List of Gossip Girl characters
The following is a list of characters for The CW teen drama Gossip Girl. The series is based on the popular book series of the same name written by Cecily von Ziegesar. The series featured nine regular characters: Queen bee Blair Waldorf (Leighton Meester), her best friend, it girl Serena van der Woodsen (Blake Lively), Serena's new love interest, loner Dan Humphrey (Penn Badgley), Blair's boyfriend, the golden boy Nate Archibald (Chace Crawford), Dan's little sister, insecure freshman Jenny Humphrey (Taylor Momsen), Nate's best friend, wealthy playboy Chuck Bass (Ed Westwick), Dan's best friend and ex-lover, the creative Vanessa Abrams (Jessica Szohr), Serena's mother, socialite Lily van der Woodsen (Kelly Rutherford) and Dan's father, former rock star Rufus Humphrey (Matthew Settle), all of whom reside in the Upper East Side of Manhattan or Brooklyn. Momsen and Szohr left the series in season five, while Kaylee DeFer was added to the main cast, portraying Ivy Dickens, a con artist who pretends to be Serena's cousin Charlie Rhodes. The series is narrated by a seemingly omniscient character, "Gossip Girl" (voiced by Kristen Bell).
- 1 Main and Recurring Cast
- 2 Main Characters
- 3 Other Characters
- 3.1 Family members
- 3.1.1 Anne Archibald
- 3.1.2 Howard Archibald
- 3.1.3 Bart Bass
- 3.1.4 Jack Bass
- 3.1.5 Alison Humphrey
- 3.1.6 CeCe Rhodes
- 3.1.7 Cyrus Rose
- 3.1.8 Scott Rosson
- 3.1.9 Maureen van der Bilt
- 3.1.10 Tripp van der Bilt
- 3.1.11 William van der Bilt
- 3.1.12 Eric van der Woodsen
- 3.1.13 William van der Woodsen
- 3.1.14 Eleanor Waldorf
- 3.1.15 Harold Waldorf
- 3.2 Other characters
- 3.2.1 Isabel Coates
- 3.2.2 Kati Farkas
- 3.2.3 Dorota Kishlovsky
- 3.2.4 Carter Baizen
- 3.2.5 Headmistress Queller
- 3.2.6 Penelope Shafai
- 3.2.7 Hazel Williams
- 3.2.8 Nelly Yuki
- 3.2.9 Jonathan Whitney
- 3.2.10 Diana Payne
- 3.2.11 Damien Dalgaard
- 3.2.12 Louis Grimaldi
- 3.2.13 Juliet Sharp
- 3.2.14 Ben Donovan
- 3.2.15 Russell Thorpe
- 3.2.16 Raina Thorpe
- 3.1 Family members
- 4 Guest stars
- 5 Special cameo appearance
- 6 References
Main and Recurring Cast
Characters are listed in order of which season they appeared in first.
|Season 1||Season 2||Season 3||Season 4||Season 5||Season 6||Total|
|Blake Lively||Serena van der Woodsen||Main||121|
|Leighton Meester||Blair Waldorf||Main||121|
|Penn Badgley||Dan Humphrey||Main||121|
|Chace Crawford||Nate Archibald||Main||115|
|Taylor Momsen||Jenny Humphrey||Main||Special guest||66|
|Ed Westwick||Chuck Bass||Main||117|
|Kelly Rutherford||Lily van der Woodsen||Main||96|
|Matthew Settle||Rufus Humphrey||Main||119|
|Connor Paolo||Eric van der Woodsen||Recurring||Main||Special guest||53|
|Zuzanna Szadkowski||Dorota Kishlovsky||Recurring||79|
|Jessica Szohr||Vanessa Abrams||Recurring||Main||Special guest||61|
|Michelle Trachtenberg||Georgina Sparks||Guest||Main||28|
|Hilary Duff||Olivia Burke||Recurring||6|
|Katie Cassidy||Juliet Sharp||Recurring||Special guest||12|
|Kaylee DeFer||Ivy Dickens||Guest||Main||30|
|Ella Rae Peck||Lola Rhodes||Recurring||Special guest||15|
Serena van der Woodsen
Portrayed by Blake Lively since the pilot and one of the few characters to appear in every episode, Serena Celia van der Woodsen is the it girl of the Upper East Side and best friend of Blair Waldorf. Recently returning from a Connecticut boarding school for reasons unknown to her friends, as was her departure from Manhattan a year prior to the show's beginning. Serena van der Woodsen comes across as down-to-earth for someone from the UES, but things, relationships (Dan, Nate) and opportunities (fashion shoots) seemed to be handed to her on a silver platter. Serena's past as the partying and promiscuous 'it girl' causes her to leave Manhattan for mysterious reasons. What's even more strange is that she abruptly returns to the high society world of Manhattan. During the first season, she deals with a spiteful Blair, her incident with Nate and a new relationship with Dan. Her relationship with Dan first faces the return of his best friend, Vanessa's and her gradual warming up to her, and Dan's acceptance of Serena and the high society world she lives in. Their relationship ends during her mother's wedding to Bart Bass due to her frenemy Georgina making life horrible for her and her friends. The second season has Dan and Serena renewing their relationship, but facing the reality that they could never be together, Dan's incident with a new girl and a scandal with a teacher, their residual feelings for each other and the discovery of their parents' love child. This season also sees Serena's mother, Lily, adopting Chuck Bass, thus making the two of them step-siblings. Serena leaves Manhattan during the summer and returns in the third season a local celebrity. She was with Nate, but decided to breakup with him. Serena went to Paris with her best friend Blair, trying to figure out if she wants to be with Nate or Dan. When she got back, they both were with other people. Serena decides to go to Columbia. As a freshman in Columbia, she constantly had to deal with many situations; a classmate named Juliet Sharp, plotting a lot of devious schemes to ruin her life with many reasons involving her family, her mother's secret forged signature on an affidavit sending her English professor to prison for 3 years so that Serena can admit back into Constance with cleared clean records, her younger brother, Eric, feeling lonely and depressed again, her estranged cousin, Charlie, who is a con named Ivy, hired by Carol Rhodes herself to scam out Lily's checks for money while Ivy "Charlie" started to fall for Dan, then went terribly suicidal from not taking her daily medication. In season 5, Serena starts to have feelings for Dan once again, but everything turns into chaos when she sees Dan and Blair kiss in Valentine's Day. Not only does it ruin her dreams of being again with Dan, but also her friendship with Blair. She became Gossip Girl in the "Con Heir" episode after receiving the mysterious package which contains the laptop where Georgina wrote a note. The note contains the password to Gossip Girl's website and e-mail address where all the tips are sent. Toward the end of the episode though, someone who claims that she is the real Gossip Girl sent her a message and told her that she wants the password so that she can have her site back. During the beginning of the episode "It Girl, Interrupted" she messaged GG and said she will return but she will do something first. After a fight with Blair that ends their friendship, Serena has sex with Dan at the Shepard's divorce party and records it as a way to get back at Blair, but gets caught by Dan, who ends his friendship with Serena also. Serena is last seen on a train doing cocaine with a guy. In season 6, after being missing for the entire summer, her friends search for her, thinking the worst. They soon find her okay and in a happy relationship under the alias: Sabrina. She also wants nothing to do with her friends, as she is in a good place. After the truth about her life is revealed, Steven and Serena go back to New York, where Serena has to deal Steven's seventeen-year-old daughter and Nate's new girlfriend, Sage, who sabotages her relationship with Steven. Dan befriends Serena, in order to get a story out of it. He then falls for her once again and they later kiss, which makes them an official couple once again. Later in the season, Dan launches a terrible story about Serena, which causes them to break up and for Serena to leave as Dan slips another story about Serena into her bag which turns out to be another version of the story but all of the great things about her. She confronts him and asks which story is the "real him" and demands answers and a recap on their history. It is then revealed that Dan and Serena first met at an Upper East Side party at Blair's house, which they had talked for a bit, but Serena was drunk. He then decided to try to get to know her, but he knew that he could never enter the world that she lives in unless he writes himself into it. It is finally then revealed that Dan Humphrey is Gossip Girl. Serena is at first upset but then finds it funny, after realizing that it all makes sense. She also realizes that without Gossip Girl, she would've never realized that the people in her life are all family, if she had left. In the end of the finale, it skips ahead 5 years and reveals that Serena and Dan get married.
Portrayed by Leighton Meester since the pilot and like Serena, one of the few characters to appear in every episode, Blair Cornelia Waldorf is the queen bee of the social scene of Manhattan and Constance Billard High School. An only child, she is introduced as the daughter of a divorced fashion designer mother and a homosexual father and the longtime girlfriend of Nate Archibald, although she also fell for and is dating Nate's best friend Chuck Bass. Blair is often portrayed as naughty, shallow, intelligent, and scheming. Despite her uptight, frivolous nature, she "works for everything she's ever gotten", in contrast to Serena, and despite her snobbish ways, she is a good friend and constantly looks out for those she cares about. Blair faces her crumbling relationship with Nate and a new, secret relationship with Chuck in the first season and her return to power as Queen Bee after a power struggle with Jenny Humphrey. Chuck leaves her alone over the summer, leading to a short relationship with a British noble during the second season. Her relationship with Chuck changes as he tries to win her back and she tries to own up to her own feelings towards him. Blair gets tired of the high school pettiness until her admission to Yale is compromised. The loss of Yale destabilizes her life plan, and she resumes her relationship with Nate in the hope of getting back on track, only to realize that he was meant to be her "high school boyfriend". By the end of the second season, Blair and Chuck embark on a relationship, continuing on into season three and dissolving into chaos at its end. Season four sees Blair trying to juggle her feelings for Chuck, her aspirations to be a successful woman and the opportunities offered her by Prince Louis, whose love will mean she has to give up on Chuck. At the end of the season, Chuck chooses to let her go, believing that he is incapable of making her happy, and she accepts Louis' proposal of marriage. In season five, Blair finds out that she is pregnant with Louis' baby, which produces conflicting feelings as she starts to find herself drawn to Chuck again. After a heartfelt apology from Chuck, the two are ready to run away and start a new life together, before they are badly injured in a car crash. Blair loses her baby and almost loses Chuck; as a result, she makes a promise to God to keep her vows to Louis and never be with Chuck again, as long as Chuck's life is spared.In the season six finale she and Chuck get married and in the five year jump shows them still happily married and have a son called Henry.
Portrayed by Penn Badgley since the pilot and the only character other than Serena, Blair and Gossip Girl herself (and the only male character) to take part in every episode, Daniel Randolph "Dan" Humphrey is the son of a rock musician turned art gallery owner, Rufus Humphrey, and absentee mother Allison Humphrey, and the elder brother of Jenny Humphrey. He first meets Serena van der Woodsen at a party where she seemed to be the only person who spoke to Dan when she greeted him. Smitten with Serena, he finds himself immersed in her moon-eyed world when he is made to attend St. Jude's at his father's bidding. Dan is an aspiring writer who dedicates his first poem to Serena and later becomes an assistant to a popular writer. He initially dreamed of attending college at Dartmouth but decided to pursue Yale, believing it to have the better English faculty. His recent break up with Serena eventually changes his luck with women, but he still has feelings for her, which leads to Serena breaking up with Aaron and the two renewing their relationship—until news of a love child between their parents makes the road quite rocky for them. He then becomes involved in a scandal with a teacher named Rachel Carr, which leads to the two ending their relationship for the final time. He now attends NYU after losing his money to a scheme involving Poppy Lifton and Serena's new love interest, Gabriel Edwards. With Rufus and Lily's relationship heading towards marriage, Dan has adapted to his family's new wealthy lifestyle. Dan has becomes a well-known face amongst the freshmen in NYU—unlike Blair who becomes a social pariah—and starts dating Olivia Burke, a Hollywood actress. The two break up when Olivia sees that Dan and Vanessa have feelings for each other. In season four, Dan begins to spend time with Blair, who he becomes close friends with and pines over, though she states that she has no romantic feelings for him and is engaged to a prince. However, it seems that he retains strong feelings for her, despite the fact that she struggles between choosing either Louis or Chuck. Dan is there for Blair whenever she needs him to be, like when she sneaks out of her wedding reception to get a divorce. He eventually lets Blair know how he feels about her with a kiss, and she in turn discovers that she likes him too. Dan and Chuck acknowledge that there may be some competition over Blair, but Blair soon makes it clear that Chuck Bass doesn't have her heart anymore. Dan and Blair are together at the end of the March season 5 hiatus. However, Dan is heartbroken when he learns that Blair chooses Chuck in the season finale. He then has sex with Serena at the Shepherds' divorce party. In the end, he leaves Serena and goes to Georgina to ask her to help him to write a book about the real scandalous stories of the Upper East Side. In season 6, Georgina and Dan go to Italy where they are off Gossip Girl's radar so they can finish and publish the book that Dan has written with Georgina being his new manager. They then return to the Upper East Side and Nate, Chuck and Blair find that he wrote terrible but true stuff about them in his book. They unfriend him and continue to go on with their lives without him. Later on in season 6, Dan befriends Serena in order to get a story out of it. He then falls for her once again and in episode 5 of season 6, Dan and Serena kiss leaving them an official couple once again. Later in the season, Dan launches a terrible story about Serena which causes them to break up and for Serena to leave as Dan slips another story about Serena into her bag which turns out to be another version of the story but all of the great things about her which Serena then finds it and stops the plane from leaving to go and see Dan. She confronts him and asks which story is the "real him" and demands answers and a recap on their history. It is then revealed that Dan and Serena first met at an Upper East Side party at Blair's house which they had talked for a bit even though Serena was drunk. He then decided to try to get to know her, but he knew that he could never enter the world that she lives in unless he writes himself into it. It is then revealed that Dan Humphrey is Gossip Girl and everyone finds out with him asking Nate to launch it off in The Spectator. Finding that Jenny knew all along, everyone is surprised but then realizes that it is not a coincidence and that it makes sense with a few flashbacks. In the end of the finale, an epilogue taking place five years later reveals that Serena and Dan get married.
Portrayed by Chace Crawford since the pilot, Nathaniel Fitzwilliam "Nate" Archibald is torn between Serena and Blair – both of whom he has romantic histories with, the so-called golden boy also frequently finds himself making life decisions. His closest friend is Chuck Bass. After his relationship with Blair ultimately falls apart, he has a fling with Vanessa Abrams. When his father flees New York to escape the FBI, Nate enters a relationship with an older married woman, Duchess Catherine Mason Beaton. The relationship turns into an arrangement of sex for money when the Archibalds' accounts become frozen. Without any funds, Nate temporarily moves in with the Humphreys. He briefly has a crush on Jenny, but it never turned out to be anything serious. In the second season, he pursues a relationship with Vanessa but when Nate gets in touch with his grandfather again, their relationship declines and he breaks up with Vanessa because of Blair in the end. They eventually break up and he goes on a trip to Europe for the summer. He returns in the third season in a Romeo and Juliet relationship with Bree Buckley, but ends up being used for Bree to get her revenge on Carter Baizen, thus ending their relationship during Lily and Rufus' wedding. He is also seen having a relationship with Raina Thorpe in Season 4 and goes on a round the world trip with his best friend Chuck. He tries to bring his parents together in season 4, but fails. He also has a relationship with both Ivy Dickens, and the real Charlie Rhodes in season 5. He also becomes the chief editor of the New York Spectator and with the help of his new love Lola, tries to find out the identity of Gossip Girl. In season 6, Nate gets involved into a relationship with Sage, the 17-year-old daughter of Serena's boyfriend, Steven. They later break up due to differences but remain good friends on their quest to finding out who Gossip Girl is. Nate also gets involved in dirty business with Chuck's father, Bart, but after he dies, he is left free and in complete control of his website. Dan, later gives Nate an envelope which he doesn't read but posts it to the Spectator. In it contains the identity of Gossip Girl, who turns out to be Dan. Nate is at first upset but later realizes that Gossip Girl hasn't done that much damage to his and his friends' lives. Five years later, it is revealed that The Spectator is extremely successful and he may be running for Mayor of New York.
Portrayed by Taylor Momsen from seasons one to four and as a special guest character in the series finale, Jennifer Tallulah "Jenny" Humphrey is introduced as a freshman at Constance Billiard with a desire to carve her own place in the popular crowd. Jenny is impressionable and quickly becomes the pawn of several characters. She, amongst other girls, harbors a crush for Nate Archibald. Jenny also has a tight-knit relationship with her brother, Dan, which proves handy as she finds herself in frequent need of help due to her bad judgment. Jenny dreams of becoming a designer and her efforts eventually pay off after receiving a letter of internship at Eleanor Waldorf's studio. When Jenny begins to feel that Eleanor is exploiting her talent, she teams up with a bad-girl model Agnes to jump-start her own line, J Humphrey Designs, to disastrous consequences. She returns to Constance and slowly transitions to become her own person. By the end of the second season, Blair crowns her as the new Queen Bee. In the third season, Jenny's position as queen begins eroding her friendship with Eric and her own personality. She then hooks up with a drug dealer and tried to lose her virginity with him, but stopped just in time. At the end of season three, she ends up losing her virginity to Chuck. She was then shipped off to live with her mother. The following season, Jenny returns to Manhattan only to be once again foiled by Blair and Chuck. She retaliates by revealing the secret of her intimate relationship with Chuck. Her next arrival involves a scheme with Juliet and Vanessa to take down Serena. As the plot gets out of hand, she is alienated by her family after Vanessa reveals that Jenny was behind the scheme initially. Fearing another encounter by Blair, she gives Blair useful information about Juliet's true intentions, as well as her and Vanessa's involvement. She leaves New York City for Hudson for good to avoid further drama. It is revealed in the Season 5 premiere episode that Jenny is now attending Central Saint Martins College of Art and Design in London, England. Jenny does not appear all throughout season 5. Dan reveals to Rufus, that Jenny knew he was Gossip Girl from the beginning and that she wanted to be on Gossip Girl. It is also revealed that Jenny had Dan as Gossip Girl send out a blast telling everyone that she lost her virginity to Chuck, in order for Blair to run her out of New York because she knew she did not have the strength to leave on her own. In a flash forward in the series finale, Jenny returns with Eric to attend Dan and Serena's wedding. It is also hinted that Jenny is now business partners with Blair, after she is seen holding a bag with the words, J by Waldorf on it.
Portrayed by Ed Westwick since the pilot, Charles Bartholomew "Chuck" Bass is cynical, world-weary, handsome, and suave. Chuck has no qualms about living life on the edge. As Nate's childhood best friend, his reputation of womanizing and a patron of baser habits make them complete opposites. He is the only son of Bart Bass, and his mother is thought to have died in childbirth. Portrayed firstly as the 'bad boy' of the group, Chuck demonstrates a nicer side in the succeeding episodes when he lends Nate $10,000 to get out of a shady poker game, falls in love with Blair, and acts as a surprisingly supportive stepbrother to Serena and her brother Eric. He and Blair finally become a couple towards the end of the first season, yet Chuck's insecurities and fear to let anyone close, cause him to leave Blair waiting at the helipad on their supposed trip to Europe. During the second season, Chuck's activities revolve mainly around winning Blair back, realizing who he is and struggling with his devious nature, the death of his father, and confronting his deviant uncle Jack Bass. Lily quickly then adopted him, legally making her his stepmother and guardian, to save B.I. from Jack. At the end of the second season, Chuck finally tells Blair that he loves her and the two share a romantic kiss. The third season starts with Chuck and Blair playing games to keep their relationship interesting, and Chuck then begins a new mission of making a name for himself and getting out of his father's corporate shadow. He finds his real biological mother, but is doubtful about her at first. She turns out to really be his mother, but lies and says she is not after she betrays him by being involved in a plot with his scheming uncle, Jack Bass, the details of which involve filing a lawsuit against Chuck and taking away the ownership of his hotel. Chuck makes a deal with Jack to trade ownership of the hotel for sex with Blair, then tricks her into going through with it. Jack reveals all to Blair, who breaks up with Chuck despite his insistence that she followed through of her own volition. They briefly reconcile at the season's end, and Chuck is about to propose when Dan reveals that Chuck has slept with Jenny. Blair, brokenhearted, tells him she never wants to speak to him again, and Chuck goes off on a bender around Prague and is shot in defense of her engagement ring. He is saved by Eva, a young French woman who briefly redeems his dark character until she is run out of town by a jealous Blair. Chuck vows revenge and begins to sabotage his former love at every turn, a plan which eventually falls apart and brings them back together. They separate for reasons of personal growth and agree to wait for each other, but Chuck begins a relationship with Raina Thorpe, as does Blair with Prince Louis. His jealous side flares up often, such as when he publicly humiliated Dan Humphrey after hearing that Blair kissed him and said that it was "life changing". At news of Blair and Louis' engagement, Chuck blows up and smashes a window, harming Blair and showing his dark side. When Blair finally realizes that what she has with Chuck is great love, Chuck lets her go to Louis because he can make her fairy tale dream come true. In season five, he's seen doing some dangerous things to feel pain, however he only feels it when Blair tells him that she is pregnant with Louis's child. After a few meetings with a counselor, a new Chuck Bass is seen. He tries to stop Blair's wedding but fails. It is revealed in the episode "It Girl, Interrupted" that Elizabeth Fisher is not his mother and that he paid Blair's dowry. Later we find out that Elizabeth is indeed his mother and Diana Payne was lying about being his mother to protect the secret about his father, Bart Bass being alive. Towards the end of the season, Bart takes away Bass Industries from Chuck and tells him that he is still an immature boy who always puts Blair Waldorf first even though she always bets against him. He then joins forces with his Uncle Jack to take down Bart. In the season finale, Blair is seen confessing her love for Chuck and telling him that she is going to fight for him. Chuck sounds the majority of Season 6, in a battle to take down Bart. In an effort to reconcile, Bart tells Chuck to get on a plane, which later explodes. Chuck is revealed to not have gotten on the plane and that Bart tried to have him killed. During Bart's Man of the Year award, Bart and Chuck have a confrontation on the rooftop, in which Bart falls off the roof. Chuck decides not to help in fear that he will hurt him and his friends and lets Bart fall to his death. Chuck and Blair later go into hiding and then decide to get married with their family and friends there at attendance. Chuck is later arrested, but he and Blair are let free when Bart's death is ruled an accident. Five years later, it is revealed that Chuck and Blair have a son named Henry.
Portrayed by Jessica Szohr from seasons one through four, starting as a recurring character in season one episodes 6 until 12 and a main character since season one episode 14, Vanessa Marigold Abrams is the childhood best friend of Dan Humphrey. Prior to Dan's relationship with Serena, she and Dan were inseparable, and the two developed a mutual attraction that was dashed when she moved to Vermont. A year later, she returned to move in with her big sister, just as Dan was trying to make things work out with Serena. Despite her continued attraction to Dan, she backed off when she saw that Dan genuinely loved Serena. Later, she strikes up a relationship with Nate Archibald but they break up before the summer and resume by the time it's over. Unlike most of the cast, Vanessa is home-schooled having been raised by outgoing parents who scorn modern society, and thus has the free time to man a café she added to Rufus's art gallery during his summer absence. After many complications with Nate, ranging from his summer fling with Catherine Mason and subsequent troubles, his sudden relationship with Jenny and his return to the Vanderbilt family circle, their relationship ends when Nate and Blair get back together. Nate's one-time favor of her applying to college has led her to attend NYU. At the start of season 3, Vanessa then embarks on a relationship with Scott Rosson that ends when she is forced to let him go because of the damage it could do to Rufus and Lily's relationship. She later begins an on-again, off-again relationship with Dan. In Season 4, Vanessa's relationship with Dan is jeopardized when she learns that Dan may have resumed his feelings for Serena, and may be the father of Georgina's baby. Forever considering herself an outsider to the scandalous high society life, she befriends Juliet Sharp as they plot (along with Jenny) the take down of Serena. Alienating herself from Dan because of her one-time alliance with Juliet, she is ousted by her friends and shunned socially. Ultimately by the end of Season 4, she decides to leave Manhattan and everything—including Dan—behind and start a new life studying abroad in Barcelona, Spain. But before she does, she steals a rough draft copy of Dan's book and shows it to a publisher who offers Vanessa money for the book (with Dan's name remaining anonymous). Vanessa says that the author will come forward after the book is published, however she asks the publisher to send her the money to her new residence in Barcelona, where she claims she will pass it on to Dan. Vanessa makes a cameo appearance in the series finale where she is shocked to find out that Dan is Gossip Girl.
Portrayed by Michelle Trachtenberg in seasons one till six, Georgina Sparks is a ruthless, manipulative girl from Serena's past who returns to New York City in the final episodes of season one after escaping drug treatment in Utah. Before that, she was supposed to be at an Equestrian circuit but sold her show pony for cocaine, prompting her parents to send her to rehab. Being Serena's friend, she wants Serena to be back to her old self and join her in doing things they used to do together. Her sudden return causes Serena to relapse into her old habits and even fixes Serena's drink which causes her to wake up late for her SATs. After Serena asks that she leave Manhattan, she becomes even more determined to ruin her life. Georgina persuades Dan to almost sleep with her, but this leads to a confrontation with Serena. Blair, taking matters into her own hands, informs her parents of her location, persuades Dan to make Georgina fall for Blair's trap and is sent to a reform school recommended by Blair herself. She reappears late in the second season where Georgina is at a church camp and appears to be a completely reformed "saved" Christian. That is, until Blair persuades her to help them in a plot to take down Poppy. After which, Georgina goes back to her old scheming ways. At the end of the second season, she is about to attend NYU and requests Blair as her roommate. She reappears in the first few episodes of the third season and surprises Blair Waldorf when she shows up as her lovely roommate. After her relationship with Dan is once again thwarted, followed by blackmailing Vanessa and ruining Rufus and Lily's wedding, she gets tricked and sent away with a Russian prince, a plan to get rid of her set by Blair and with the assistance of Dorota, by exiling her to Europe. At the end of season 3, after a long absence, Georgina returns to New York City from her enforced exile in Belarus disguised by wearing a blonde wig and a large coat, desperately seeking the help of various Upper-East Siders with her "problem". It is revealed that Georgina is pregnant, and claims it is Dan's child. At the start of season 4, she runs off again, leaving Dan with their son Milo but it is later revealed that he is not the father and that it was just another one of Georgina's schemes. Georgina takes Milo back when Dan signs the birth certificate, ending her manipulative plot and leaves Dan. Georgina later returns at the very end of season 4 for the Constance Billiard alumni event in hopes of stirring up drama. She reveals to Serena and others in attendance that she is currently living in Bedford, New York, is married to a young Wall Street stockbroker intern, and is outright bored with her current lifestyle of being a stay-at-home-mother. Georgina accidentally learns the secret behind Serena's cousin Charlie and informs her to keep in touch. In Season 5 at Blair's wedding, it is revealed that Georgina steps in as the 'new' Gossip Girl, the anonymous narrator of the series, as the 'real 'Gossip Girl' abandoned her post following Chuck and Blair's accident. In the season 5 finale, it is revealed that she will help Dan write his follow up to "Inside". Having left him for Chuck, Dan promises to write the book that he should previously published, which Georgina, who has her own score to settle with the Upper East Side, is more than happy to help him with. In the series finale, she is shown to be in a relationship with Jack Bass and helps Blair and Chuck with their problem regarding Bart Bass.
Ivy Dickens, portrayed by Kaylee DeFer, joined the series late in season four as a recurring character and became a main character from season five onwards. She came to New York pretending to be Serena and Eric's cousin Charlotte "Charlie" Rhodes. Once Charlie arrives in Manhattan, she is amazed by the glamorous lifestyle of her relatives, especially her cousin Serena. More importantly, with she feels that she finally has the loving family that she never had. Much to the chagrin of her mother, Carol, Charlie decides to prolong her stay in Manhattan. She begins to set her sights on Dan and decides to blackmail Vanessa to get on his good side. Trouble ensues when Charlie's mental behavior wreaks havoc on the Upper East Siders, which leads to Charlie leaving New York. Back in Miami it is revealed that Charlie is actually a professional actress that goes by the name of Ivy, who was hired by Carol to get access to the real Charlie's multi-million dollar trust fund as well as to keep her identity a secret. During the season five premiere, it is revealed Ivy has since moved to LA with her boyfriend, Max. Serena, who has been in LA since the beginning of summer, encounters Ivy in the restaurant she is working at and invites her to lunch. Ivy resumes to identity of Charlie whilst with Serena. After Serena invites "Charlie" back to New York, Ivy is initially uncertain, but later agrees and leaves Max. Upon their arrival to New York, Ivy is confronted by Carol. Ivy blackmails Carol, telling her that she will expose their secret unless she is allowed to stay in New York under the identity of Charlie. Carol hesitantly agrees and leaves New York. During her time in New York, Ivy's identity is discovered by Diana Payne, a powerful media mogul who owns 'The Spectator' newspaper, and even Max who is in New York looking for Ivy. Even though Serena, CeCe, Lily and Rufus are told the truth, none choose to believe it. During a ball thrown by Lily to help "Charlie" become integrated into New York society, Ivy sends a tip to Gossip Girl sharing the location of Blair and Chuck's getaway car to divert attention away from her in case her secret is exposed. When Chuck and Blair are hospitalized after a car crash, Ivy decides to leave New York. A private investigator hired by Lily to find "Charlie" tracks down the real Charlotte Rhodes who has been living in New York under the name of Lola, unbeknownst to her mother. Ivy returns to New York where she is reunited with Charlie after it is revealed they were in the same acting class in Miami. She then leaves New York, unable to tell Lily an important message. Ivy is staying with a terminally ill CeCe in a care home in the Hamptons, taking care of her. When CeCe is hospitalized, Lola becomes suspicious as to why Ivy is using her name leading to Ivy and Carol's secret being uncovered. Ivy is then cast out of the family by Serena which is followed by the death of CeCe. At the reading of the will, it is revealed that CeCe's entire estate has been left to Ivy, much to the chargrin of Lily and Carol. This suggests that CeCe knew about her identity before her death. Ivy then kicks Rufus and Lily out of her inherited apartment and makes it her quest to become accepted on the Upper East Side. Her plan ultimately fails, but she agrees to help Lily to take down Carol for her actions. For this, Lily pays her $1,000,000, which she rejects since what she truly wants is to be forgiven and that she does not care about the money, but about her "family." However, Lily just bids her goodbye. Hurt, she later makes a new plan with Lola to take Lily down. In season 6, Ivy begins seeing a newly divorced Rufus, as part of her plan to destroy Lily. It is revealed that she is working with and dating William, who is also in on the plan. After Rufus sees them together, he breaks up with her. In the series finale, William reveals that he played Ivy in order to get back together with Lily, leaving Ivy devastated. Five years later, Chuck is seen reading a newspaper with an ad to see a movie adaptation of Ivy's autobiography starring Lola and Olivia Burke.
Lily van der Woodsen
Portrayed by Kelly Rutherford since the pilot, Lillian Celia "Lily" van der Woodsen (née Rhodes; previously van der Woodsen, Humphrey, Mueller, and Bass) is the multiple-divorced, ex-ballerina and socialite mother of Serena and Eric van der Woodsen, biological mother of Scott Rosson, adoptive mother of Chuck Bass, and stepmother of Dan and Jenny Humphrey. Lillian has a colored history as a former groupie of Dan and Jenny's father, Rufus, that she would rather not acknowledge. Her previous marriage before Rufus Humphrey, was to Bart Bass. Before Bart Bass, she was divorced from Dr. William van der Woodsen. Despite her constant concern for appearances and status in high society, it can be assumed that she lived as indulgently as Serena during her wild child years. Her similarity to Serena can especially be seen when she cries and is unable to make any decisions, both of which are behaviors commonly seen in Serena. It is revealed she was also institutionalized at 19 much like her son Eric. It was later revealed that it was not because of a suicide attempt, but because she was pregnant with Rufus's child. The son she gave up, Scott, came to New York to find them. Rufus and Lily returned to New York, and became a couple. The character is portrayed by Brittany Snow in flashback sequences. She adopts Chuck Bass in the second season after Bart's death. In the last episode of the second season, Lily and Rufus became engaged and married in the fifth episode of the third season. At the end of season 5, when Bart Bass is found alive and well, one of Lily's marriages needs to be annulled, and because of the recent difficulties Lily has been facing with Rufus, she chooses to end her marriage to Rufus and pursue a life with Bart. In season four, Lily becomes a "grandmother" from Georgina and Dan. Dan and Georgina name the baby Milo Humphrey. It is later discovered that Dan is not the biological father of Milo. It was revealed that Lily had put Ben Donovan in jail for having an "affair" with Serena, which was the current rumor at Serena's school in Connecticut. As revealed in the flashback sequences, she was raised in Montecito, California by her father Rick Rhodes; who was a music producer and her mother Celia "CeCe" Rhodes who was also a socialite and raised on the Upper East Side, who later dies leaving Lily heartbroken. In season six, Lily is caught between her loyalty to Chuck and her loyalty to Bart. When Bart dies, William consoles Lily as she deals with the stress. In the series finale, Lily is shown to be in a relationship with William, but is also in a good place with Rufus, who is dating Lisa Loeb.
Portrayed by Matthew Settle since the pilot, Rufus Humphrey is a former rock star whose marriage has fallen apart. He is also an owner of a fledgling art gallery. Determined to give his children a quality education, he enrolled them at private day schools which lead him to bump heads more than once with his former flame, Lily van der Woodsen. He got a divorce from his wife, Alison Humphrey who was having an affair with a man named Alex. He has difficulty, as a single parent, managing his growing children, in particular the strong-willed Jenny, and often enlists Lily's aid. Although he and Lily attempted to rekindle their old relationship prior to Lily's marriage, she ultimately chose to remain friends with Rufus and to marry Bart Bass. After Bart's death, the pair rekindle their romance when they search for their son. In the last episode of season two Lily and Rufus became engaged and married in the fifth episode of season three. In season four, Rufus doesn't believe Georgina when she says that she and Dan have a son, Milo Humphrey. In the season four "Double Identity" episode, Rufus finds Milo's ID bracelet, which says that Milo has a different blood type than Dan. When Bart Bass is found alive and well, one of Lily's marriages needs to be annulled, and because of the recent difficulties Lily has been facing with Rufus, she chooses to end her marriage to Rufus and pursue a life with Bart. In season six, Rufus gets into a relationship with Ivy, but breaks up with her after he catches her cheating with William. When Dan is revealed to be Gossip Girl, Rufus is immediately furious at the fact that he hurt his friends and his sister, Jenny. Dan explains that Jenny knew all along that he was Gossip Girl and that she wanted to be on the site. After coming to the realization that Jenny has a better life away from New York, he finally understands. In the series finale, Rufus is shown to be in a relationship with Lisa Loeb, but also in a good place with Lily.
Voiced by Kristen Bell, "Gossip Girl" is the narrator of the show, an unseen character whose gossip commentary blog is widely visited by the youths of the Upper East Side social scene, often stirring the lives of the main characters. Her identity remains a secret but still manages to lure readers with catty wordplay and scandalous news provided via tips through the members of the Upper East Side social network. Gossip Girl has avoided discovery twice: first, when her blog was the subject of getting shut down during Dan's incident with Miss Carr; and second, when Serena attempted to confront her personally in the second season episode, "The Graduates," by texting her and saying she knows Gossip Girl's identity. However, this second attempt ultimately failed, as Gossip Girl invited the entire class with her, masking her identity. Gossip Girl then gave everyone the perfect present: A clean slate and that she will be following them to college. Gossip Girl showed a personality trait in the fourth season episode, "The Townie", where she responded to a request from Blair for the location of Juliet with the address and "find the bitch," showing that she does not appreciate anyone who may threaten the validity of her blog, leading one to believe she may be personally motivated. In the fifth season episode, "G.G.", it shows Georgina Sparks behind the computer posting a message as Gossip Girl, but in the following episode she reveals to her husband/accomplice that the real "Gossip Girl" abandoned her post following Chuck and Blair's accident. Serena becomes "Gossip Girl 3.0" in the season five episode, "Con Heir", after Georgina ("Gossip Girl 2.0") sends the power laptop and the blog's password to her. The real Gossip Girl steals back her post with the power laptop in episode 22, "Raiders of the Lost Ark," with the help of Nate and Lola. In the series finale, Sage advises Nate to find out who Gossip Girl really is after seeing his old research of Gossip Girl. Nate had to give up his research as a part of the deal for information from Gossip Girl herself. With everything resolved, Nate is now determined to find out who Gossip Girl is by going through his research again. Dan had been releasing chapters of his second book to multiple blogs, each containing stories specific to one person, with disastrous aftermaths. The final chapter of the book was given to Nate from Dan, who uses it to propel The New York Spectator forward in the ratings. Everybody gets a message from The Spectator, revealing Dan as Gossip Girl all along. His true motivation behind Gossip Girl was his love for Serena and the need to get in the elitist world of Manhattan, which Dan couldn't get because he wasn't born into that world. One moment, years in the past, Dan accidentally got in a birthday party of someone, he met Serena for the first time and fell in love with her. After that, Serena disappeared and Dan vowed himself that one day he would be a force to reckon with. So he made the identity of Gossip Girl himself, and posted the first post about Serena in the ninth grade. Just soon after Gossip Girl was established, he got the tips and e-mails from everyone in New York. When Serena returned from boarding school, Gossip Girl becomes really famous by sending the news to everyone that Serena was back in town. Everyone comments that Gossip Girl was not at fault but everyone else for providing Gossip Girl with the information. With Dan revealing his identity to the world, Dan declares that Gossip Girl is officially dead. In the flashforward, we are shown a new generation of kids as Gossip Girl narrates: "You may be rid of Dan Humphrey, but you'll never be rid of me. There's always someone on the outside, wanting to get in. Who am I now? That's a secret I'll never tell. XOXO, Gossip Girl.", revealing that five years later someone else is Gossip Girl, and that the legacy goes on."
Recurring characters who are family to one or more main character. Names are listed alphabetically.
Portrayed by Francie Swift in seasons one, two and four, Anne Archibald (née van der Bilt) is the mother of Nate Archibald. During the events of the first season, she aids her husband in dealing with Eleanor Waldorf's accounts. She once promised to Eleanor Waldorf to give Blair her Cornelius Vanderbilt engagement ring should Nate and Blair ever be engaged but when Blair witnesses Nate's troubles with his father she ends the relationship. By the second season, Nate's mother whose financial assets have been frozen since her husband's guilty departure have caught up with her and their house in Manhattan is seized, leaving Nate to lodge in temporarily with the Humphreys. Anne Archibald's reputation was also in danger during her financial situation with Chuck giving her loan after selling his club, Victrola but this causes Nate to end his friendship with Chuck. Her financial troubles come to an end when Nate convinces his father to come clean to the FBI and she sheds tears for the arrest of her husband. A short while before her husband is released from prison however she files for divorce.
Portrayed by Sam Robards in seasons one, two, four and six. Howard "The Captain" Archibald is the father of Nate Archibald. Howard is a white-collar criminal and a recovering cocaine addict. He leaves to escape arrest, still addicted to cocaine and Nate punches his father before the Captain could get into his limo and fled to Dominica. In the second season, when he returned to New York, to take Nate and his mother with him, Nate gave him a choice. Either go back to Dominica and never speak to his family again or turn himself in to the police. Howard decided to do the right thing and chose to turn himself in. In the fourth season, Howard later receives a file for divorce while in jail, a few months before his release from prison. When he is paroled, Howard soon takes a job with Russell Thorpe.
Portrayed by Robert John Burke in season one, two, five and six, Bartholomew "Bart" Bass, is Chuck's billionaire father, founder of Bass Industries and was married to Lily van der Woodsen. His family lived at the New York Palace Hotel, which he owned. His money was self-made, as opposed to inherited like most Upper East Side families. He was controlling with his family, ruthless in business and demonstrated little affection for Chuck, and it's revealed that this is because he holds his son responsible for his late wife's death (Chuck's mother died while giving birth to him.) At times Bart appears to care about his son, and asked him to be his best man at the wedding. Bart complimented Chuck on his speech, and said he was proud of his commitment to Blair. In season 2, with Dan's help, he and Chuck try to mend their relationship, but he suddenly dies in a limo accident. In season 3, he reappears as a ghost on the anniversary of his death. In season 5, Diana Payne claims that she is Chuck's biological mother, conceiving him after she and Bart had an affair, but it is revealed to be untrue. When looking for Diana's secret, he is discovered alive. As Life on the Upper East Side goes on with its gossip and rage of others, Chuck finds out something he was not supposed to about his father and how he pays people off to "accidentally" kill people who are after him and with information that could destroy his reputation. As Chuck and Blair keep digging for dirt on Bart, He gets Nate into prison and tries to kill his own son in a flight to Moscow as a deal to Chuck to keep everyone he loves safe. As a party is going on for Bart, it is then announced that there was a plane crash which turns out to be a Bass industries private jet which is the one that Chuck was in. As Dan gives hits heart felt speech about what was supposed to be Bart, Dan reveals it was not Bart he was talking about, it was Chuck as he steps onto the stage and reveals in front of the cameras that his father tried to have him killed. Bart tries to fix the mess that Chuck had done while having him taken to the roof top to the building by his guards and leaves saying that Chuck is going to be put in an institute for his delusional mind set. As Chuck tries to get the truth out of Bart on the roof top, Bart threatens Chuck which leads to Chuck hitting Bart and Bart hanging from the side of the building as Blair approaches the scene. Bart eventually slips and falls off of the cliff without any regret from Chuck and a horrified Blair.
Portrayed by Desmond Harrington in season two, three, four, five and six. Jack Bass is Chuck's uncle who comes to New York upon hearing of his brother, Bart Bass' death, and slept with Blair on New Year's. Jack headed Bass Industries in Australia and served as Chuck's legal guardian when Bart died. He then plots to take Bass Industries from Chuck and sets him up by having the Board of Bass Industries to witness his debauchery and inebriation. Chuck turns to Lily to remove Jack from Bass Industries due to his incompetence at handling the assets of Bass Industries causes the business to become stagnant. Jack loses hold of Bass Industries when Lily decides to become Chuck's new legal guardian, thereby transferring a significantly large power of the company to her. Jack then confronts Lily while he is high and attempts to rape her until Chuck has him kicked out of the opera. Jack is then sent back to Sydney. By the third season, during Chuck's opening of his new hotel, Blair aids him in getting a liquor license for Chuck by contacting Jack. Chuck confronts Blair for contacting Jack and Blair receives flowers and a note stating that the liquor license is fake. Blair and Chuck eventually allow the police to end the opening party and therefore receive enough press and publicity for future clients for a genuine speakeasy that Chuck has been planning. Chuck goes to find Jack, whom could maybe help him take back Bass Industries from Lily, who is going to sell it. Jack returned to help Chuck in season four. in season 5, Jack, back to New York to thank him for saving his life in the car accident by donating blood, but starts to doubt Jack's story when Chuck investigates and learns that Jack was recently diagnosed positive with Hepatitis C, and a test on Chuck turns to be negative. At the end of episode, Chuck finds out that it wasn't Jack who saved his life and assumes it was Elizabeth Fisher, Jack appears to verify his story by saying that she didn't want him to know. Although, near the end, there is a scene with Jack in his limo calling someone and telling her that Chuck knows that Jack didn't donate him the blood, and that she should come. In prior episodes to episode 22 "Raiders of the Lost Ark", Chuck begins to believe that Jack Bass is more than an uncle and is actually his biological father, but this isn't proved in the episode previously stated. In the series finale, he is shown to be in a relationship with Georgina Sparks.
Portrayed by Susan Misner. Alison is Rufus's estranged wife and Dan and Jenny's mother. She had an affair while living and working as an artist in Hudson, and Rufus cannot forgive her for the transgression. She returns for the holidays during the first season, but Rufus asks her to leave after a former lover attempts to contact her at the Brooklyn loft. She and Rufus ultimately ends their marriage.
Portrayed by Caroline Lagerfelt in seasons one, two, three, four and five, Celia Catherine "CeCe" Rhodes is Lily's mother and Serena and Eric's grandmother. She lives in Montecito, California and visits Lily, Serena and Eric in New York City a few times every year. She is portrayed as a very wealthy, highly conservative, uptight, intimidating, snobbish, and impassive socialite who looks down and scorns at all people who are of middle or lower classes. She caused the breakup of Rufus and Lily by making Lily choose between her family inheritance and Rufus. Intimidated, Lily chose her inheritance. CeCe also tried to break up Serena and Dan to no avail by inviting Carter Baizen (who comes from a wealthy family) to the cotillion. During the first season, CeCe manipulated her daughter and granddaughter by declaring that she had a terminal illness, claiming that the doctors found 'something' in her lungs. Although she later admitted that this was a lie to gain sympathy, she was later seen taking pills. Her cold and manipulative personality changes in the second season when she lets Dan into the White party by making him her escort, seeing that he still has feelings for Serena. After Bart Bass' funeral, she reveals the reason why Lily was in a sanatorium. During the events of Serena's arrest, Lily and CeCe resume their mother-daughter fight but later patch up their problems before CeCe leaves. CeCe's supposed sudden illness in the third season causes Lily to leave Manhattan to take care of her in California for a couple of months, with CeCe returning for an appearance on the Thanksgiving episode. CeCe returned to Manhattan in season four to support her daughter Lily's impending jail sentence along with Lily's estranged sister Carol. In the second season episode "Valley Girls", a younger CeCe is portrayed by Cynthia Watros. In Season 5, CeCe Rhodes arrives back in New York where Lily and Serena are planning to throw her a Studio 54 party in her birthday. There's a some scheme at the party about her granddaughter Charlie Rhodes that whom to be revealed as Ivy Dickens because Ivy's ex-boyfriend come to CeCe's party by invitation of Serena. After that CeCe knew all of her fake granddaughter Ivy Dickens story to herself but still love Ivy because her kindness and CeCe knew about Carol and William's affair. Ivy also finds out that CeCe is sick, but keeps it a secret. In episode 16 "Cross Rhodes", it revealed that so far who has been caring for and maintaining CeCe very well and concerned about her condition is Ivy Dickens and asked Charlie/Ivy to stay with her to the hospital because she is the only person CeCe's feel safe with. At the end of the episode CeCe dies. Ivy Dickens is announced as CeCe's heir and we learn that CeCe was apparently aware the whole time of Ivy's real identity.
Portrayed by Wallace Shawn in seasons two, three, four and five Cyrus Rose is Eleanor Waldorf's divorce attorney and an entertainment lawyer, who becomes her new love interest in season 2. Cyrus is also the father of Aaron Rose, from a previous marriage. Blair is excited to meet him at first, as she believes her mother to have the best taste in men. She is shocked to find that he is old, bald, 5 feet tall, with a crude, jolly personality, and is a 'hugger'. Blair describes meeting him as "expecting Cary Grant and getting Danny DeVito" He also has a catchphrase, "Not enough!", once using the catchphrase to comment on Blair's pumpkin pie during Thanksgiving, and on hugs and other occasions. During Blair's eighteenth birthday, she and Cyrus have a conversation about Mei Li, the 'golden lion', a Vietnamese woman he met during the Vietnam war that leads him to divorce his first wife. When Mei Li died during the Vietnam war, he didn't find love until he met Eleanor Waldorf. Blair uses this knowledge to separate to Cyrus from Eleanor but Cyrus uses the arrival of Cyndi Lauper to prey on Blair's guilt causing Blair to admit her mistake and slowly accept Cyrus. The two return to her eighteenth party to convince Eleanor to take him back. They get married the day after and announce the engagement during Thanksgiving, bringing his jolly family with him that irritates Blair. Cyrus and Eleanor get married during the 2nd season. Cyrus returns in the 3rd season and convinces Dorota to get married, buying her and Vanya an apartment in Queens.
Scott was portrayed by Chris Riggi in Seasons 2 & 3. Scott Rosson is the biological son of Rufus Humphrey and Lily van der Woodsen. He was born at a French hospital sometime in 1986, whom Lily secretly gave up without Rufus's knowledge. When Rufus discovers this, he decides he wants to locate him. He and Lilly meet with Scott's adoptive parents in Boston, who inform them that he recently died in an boat accident. But it's revealed later on that Scott's younger brother was the one who actually died. In the season finale of season 2, Scott leaves home to go to New York to find Rufus and Lilly while his adoptive parents believe he's in Portland. He pretends to be a student at NYU, and develops a romantic relationship with Vanessa. When she discovers his real identity, she helps him try to connect with Rufus and Dan. His mother reappears right before his is able to tell them the truth. Scott tells her that she had no right to keep his birth parents away from him, but she explains that she and his father were heartbroken after losing his brother, and that they were afraid of losing him to if he met rich birth parents. He decides to leave, but reappears in the episode "Rufus Getting Married" along with Georgina Sparks. He attempts to talk to a distraught Lilly, who, believing him to be a stranger, yells at him to leave her alone. When she and Rufus discover that he's their son, they rush to the bus station in order to stop him. Lilly apologizes for her behavior earlier, and says that she always wanted to meet him. The two of them, along with Rufus, embrace together and go to the
Maureen van der Bilt
Portrayed by Holley Fain in seasons two and three, Maureen van der Bilt is Tripp's wife. She reveals her more manipulative side on the 3rd season when she concocts a plan to have Trip win the Congressional seat left by the late Congressman Krueger. She hires someone to purposefully drown himself to be saved by Trip, giving him an advantage to win the election by giving him a heroic image. When Nate and Vanessa discover that the man in the video was hired to help Trip win the election, Nate and Trip accuse William and swear that they will avoid any association with him. William soon discovers Maureen's plot but only after Trip wins the election. Serena then earns her ire when she and Trip start and affair and are discovered by Chuck during Thanksgiving, with Nate revealing the affair to Maureen. An upset Maureen leaves early for Thanksgiving but returns for her jacket, identical to Lily's, and gets Lily's letter from her ex-husband. Maureen uses it to blackmail Serena, but offers her a chance to become Trip's mistress, something she and Trip have agreed on to save his career. She decides to keep her husband from getting into any more trouble and silences him when he tries to justify the accident with Serena to Nate.
Tripp van der Bilt
Portrayed by Aaron Tveit in seasons two, three and five, William "Tripp" van der Bilt III is Nate's older, "political minded" cousin, who was getting married in the second season and argues with Vanessa over Nate's future. He then convinces Nate to take the internship at the Mayor's office but Nate does otherwise by traveling to Europe for the summer. In the third season he runs for office, with Nate's help and wins the congressional seat. Tripp starts an affair with Serena when he discovers that Maureen created a plot that would win him the election. Their affair ruins his marriage and compromises his career and is discovered during a disastrous Thanksgiving. The following day, Tripp and Maureen agree to certain terms concerning Serena and his career. Serena refuses to continue such an agreement of her becoming a mistress and they fight. While on the road back to Manhattan, Trip and Serena collide towards a bridge and Tripp places Serena on the driver's seat to remove himself from any implication of arrest. Nate later punches him for getting Serena into an accident. Tripp resurfaces in Season 5 when Nate gets a tip that Tripp's wife is having an affair. Tripp causes Chuck and Blair's car accident, intending to target Nate out of jealousy.
William van der Bilt
Portrayed by James Naughton in seasons two, three and five, William van der Bilt is Nate Archibald's grandfather through his mother Anne Archibald and the patriarch of the powerful van der Bilt family. William is very proud of his family's political heritage and tries to convince Nate to follow the family business, having already convinced his cousin Tripp to do so. William appears to care for his family, but is not above manipulating them to further his own agendas, such as when he asks Blair to "talk" to Nate about going to Yale instead of Columbia. Previously, he had refused to help Nate's mother when the Captain was charged with embezzlement, leading to a falling-out between his grandson and himself. In "The Grandfather" Nate reconnects with his mother's family and his grandfather exerts his considerable influence over him, contributing to tensions with Vanessa and Blair. So far Nate has resisted William's suggestions regarding his future political career.
Eric van der Woodsen
Portrayed by Connor Paolo since the pilot, Eric van der Woodsen is the troubled younger brother of Serena and heir to the Van Der Woodsen fortune, his suicide attempt becomes the catalyst for Serena's homecoming. Revealed his homosexuality later on in season one to everyone, after his boyfriend Asher pretends to have a relationship with Jenny Humphrey. His friendship with Jenny is repaired after she apologizes in the beginning of the second season. They soon become best friends through the second season. This once again falls apart during Season 3 after Jenny accepts her role as Queen Bee but soon, Eric makes amends with her after Serena's accident. He then begins to date Jonathan Whitney but their relationship falls apart due to Eric's once obsessive need to "teach Jenny a lesson". In the next season, he begins dating a bisexual man named Elliot.
William van der Woodsen
William van der Woodsen, portrayed by William Baldwin in seasons three, four, five and six, is Lily's first husband and the father of Serena and Eric. Lily hides the fact that she has cancer from her family except her mother and goes to her ex-husband for treatment. When Rufus finds out, it causes a strain in their marriage. Meanwhile, Serena is angry with Lily for concealing this from her since Serena had been searching for her father for these past 3 years. When William comes back to the Upper East Side, he is met with hostility from his family. Lily decides that she needs him; Eric is cautious about his agenda, Serena decides she wants to get to know her father; and Rufus is angry at his intrusion. Although William really had been treating Lily, he continues to keep her just sick enough for him to be needed because he had fallen in love with her again and misses his family. Jenny wanted her Humphrey family back and the rest of the family finds out William's plot to separate Lily and Rufus. When Serena finds out, she is especially devastated, and William leaves town as the police closes in on him. He returns in season four when Lily is arrested to support his family. He also makes amends with Rufus. In Season 5, William van der Woodsen returns to the Upper East Side for the wake, and is the executor of CeCe's estate. Ivy Dickens is announced as CeCe's heir and we learn that CeCe was apparently aware the whole time of Ivy's real identity. Carol Rhodes also reveals the identity of Charlie's father as William Van der Woodsen. In season 6, it is shown that William is in a relationship with Ivy, the two seemingly working together for a plot to take Lilly down. When Bart Bass dies, William consoles Lilly about it and the two rekindle their old love. Ivy is confused when she is ready to tell Lilly about them and William claims to have never met Ivy before. In private, William reveals to Ivy that he was using her all along in a plan to get back with Lilly and coldly dismisses her. The final moments of the series reveal that William and Lilly have remarried.
Portrayed by Florencia Lozano in the pilot and Margaret Colin since episode four, Eleanor Waldorf-Rose is the fashion designer mother of Blair Waldorf. Her decades-long marriage to Blair's father, Harold Waldorf, ended when Harold left her to pursue a relationship with a French male model, Roman. It is implied through flashbacks that Eleanor knew about Harold's sexuality. Her clothing line 'Eleanor Waldorf Designs' is being distributed by Barney's and Bendel's. She once employed Jenny as an overworked intern.
Portrayed by John Shea in seasons one, two and five. Harold Waldorf is Blair's father who went to France to live with his male lover Roman. He traditionally makes pumpkin pie during Thanksgiving but hasn't made it since Blair's last Thanksgiving with him, before he came out and left for Europe. He returns for the holidays with his partner, Roman, a model once used by Harold's ex-wife, Eleanor. Roman earns Blair's spite during Christmas by breaking his leg, inviting an old flame of Roman's that frustrates Harold. Harold speaks with Blair about the incident and then shows her his life in France through a video. He now lives in France, tending a vineyard and has a cat named Cat, the same name as the cat in Blair's favorite movie, Breakfast at Tiffany's. He returns in the second season during Thanksgiving when Blair first thought that her mother didn't invite him. He and Blair share a pie during thanksgiving. He gives Blair a dog named Handsome Dan whom Blair renames Handsome. During Blair's hazing incident that sparked a controversy with Miss Carr and Dan and the almost removal of Gossip Girl's blog, Blair convinces her father and the parent's council of Constance-St.Jude's by showing a picture of Dan in a compromising position with Miss Carr, thus securing her admission to Yale. When he overhears Blair's conversation about the picture only being eerily prophetic and untrue, Harold speaks with Blair and tells her that he saw a different side of her and is disappointed that he lied for her indirectly. He then tells Blair that the college she is admitted to doesn't matter and that the person she becomes matters more.
Portrayed by Nicole Fiscella in seasons one, two and four, Isabel Coates is Blair's loyal sidekick, who remains her friend despite her losing rank as Queen Bee. She was best friends with Kati Farkas and tends to match outfits with her. During the first season, she and Kati often appeared in Blair's Audrey Hepburn dreamscapes and at one point she and Kati also appear in Dan's dreams. She is also a concert pianist. Isabel and Penelope contribute to the new rift between Blair and Serena when the position of Queen shifts from Blair to Serena. Her see-through dress that she intended to wear to the Snowflake Ball is used to humiliate Vanessa. Isabel, Penelope and Nelly Yuki are all present when they plan on declaring Emma Boardman as the new Queen, which went to Jenny. Both Isabel and Penelope refuse to have a girl from Brooklyn carry out their legacy but Blair convinces them otherwise. Isabel, together with Kati, returned at the end of season four at a Constance reunion.
Portrayed by Nan Zhang in seasons one, four, five and six, Kati Farkas is Blair's loyal sidekick until she loses her rank as Queen Bee. She was best friends with Isabel Coates and regularly matches outfits with her. During the first season, she and Isabel often appeared in Blair's Audrey Hepburn dreamscapes and at one point she and Isabel also appear in Dan's dreams. Kati's brother owns the apartment that would be the setting place for Blair's Japanese-themed seventeenth birthday, which led to Blair and Chuck's continuing secret relationship during the first season. Her parents move her back to Israel after spring break. Kati returned with Isabel for a constance event in the penultimate episode of season four and the season finale. In season five, Kati returns to compete with Blair's former minions, Penelope and Jessica, to become Blair's bridesmaid in her upcoming nuptials. In the sixth season, Kati and Jessica still continue being Blair's loyal minions.
Portrayed by Zuzanna Szadkowski since the second episode, Dorota Kishlovsky is the Waldorf's housekeeper. Despite often snapping at her in numerous episodes, Blair is shown to see Dorota as a mother figure and her closest confindant. In the web-series "Chasing Dorota", it is revealed that Dorota is actually a Polish countess with a secret husband, Stanisław. She fled to America to escape her family and began working for the Waldorfs in 2004. She eventually divorces her husband after falling in love with Vanya, the Russian doorman at the van der Woodsens' apartment building. In "The Treasure of Serena Madre" she is revealed to be unexpectedly pregnant. They get married in "The Unblairable Lightness of Being" when she finds out that her family will be visiting her. She gives birth to a daughter named Anastasia in the third season finale, and she and Vanya move into an apartment in Queens, bought for them by Cyrus.
In the season 5 premiere episode, she finds out that Blair is pregnant and covers it up by announcing her own pregnancy. She later gives birth to a son named Leo.
Portrayed by Sebastian Stan in seasons one, two and three, Carter Baizen is a St. Jude's graduate and rival of Nate and Chuck. It is mentioned that he turned his back on his parents and so was left without a trust fund and was forced to take matters into his own hands by shaping his own future, something that Carter reveals to Serena a week before the cotillion. In the second season, Carter resurfaces in New York with the mysterious Elle but ends up being involved with Blair and sleeps with her, contributing to her downward spiral. He soon leaves New York as Serena and Chuck intervene. In the second season finale, Carter returns to New York to tell Serena that he has found her father. During the premiere of season three, it is discovered that he and Serena spent their summer in Europe in pursuit of her father. In light of Serena's failure to capture her father's attention, Carter reveals his feelings to Serena and they share a kiss. Their relationship ends when it is revealed that he left Bree Buckley's cousin at the altar, earning the wrath of the Buckleys as Bree has her cousins called in during Rufus and Lily's wedding to bring Carter to Texas to work at an oil mill to pay off his debt. Serena then gambles on a high stakes poker game for Carter's freedom and fails. She then takes matters into her own hands and has him freed but Carter refuses to resume their relationship, saying that he would have preferred it if Serena didn't save him so that he could make amends and leaves. Carter resumes his habit of lying when he informs Serena of her father's definite location. Serena's disappears with him, which creates a strain in her relationship with Nate. Serena later finds out that he had known about where her father was since before they began dating, but had been delaying the information from her in order to get closer to her. She then forces him out of the limo.
Portrayed by Linda Emond in season one and the beginning of season two and by Jan Maxwell at the end of season two and for one episode in season four, Headmistress Queller is Constance Billiard School for Girls' and St. Jude's School for Boys' headmistress. Blair mentions that she and Headmistress Queller had tea when she first applied to Yale. She is first introduced in the first season as the new Headmistress and immediately faces trouble with the junior class. She pragmatically interrogates Constance Billard and St. Jude's students when an accident in the school swimming pool involving the most of the Junior class reaches her ears and threatens expulsion if the perpetrator doesn't come forward. Serena comes forward but doesn't get expelled and instead finds out that Bart Bass paid off her headmistress that earned Serena community service. In the second season, Jenny rejects a meeting with her when she has been skipping school and instead working at Eleanor Waldorf's atelier. Jenny eventually returns to Constance. In the later episodes, Blair seeks advice from her when she discovers that she is waitlisted for Yale and reassures her that all Constance students eventually get accepted as long as their transcripts are untarnished. When Miss Carr informs her of Blair's hazing against her, headmistress Queller gives Blair detention through community service. Blair's hazing incident eventually reaches the ears of Yale and Blair is no longer accepted. Blair eventually attempts to apply to Sarah Lawrence College but has no chance because of her hazing incident and that the dean only spoke with her as a favor from headmistress Queller.
Portrayed by Amanda Setton in seasons one, two, four and five, Penelope Shafai is a member of Blair's clique until she was dethroned as queen bee; and constantly shifts her allegiance between Blair and Jenny. She makes no secret of her crush on Nate when she aids in Blair's dethroning and Jenny's ascent as Queen with Jenny earning her and Hazel's favor when Jenny salvages herself after Blair attempted to sabotage her birthday. She helps host Jenny's party with Asher and gives the freshman the benefit of the doubt when she lied about having sex with Asher Hornsby, eventually ending her friendship with her when Jenny reveals the truth. She is also a national Merit Scholar. Chuck persuades her to ruin Amanda Lasher's hair which ends up in a fight between Dan and Serena. Isabel and Penelope contribute to the new rift between Blair and Serena when the position of Queen shifts from Blair to Serena. Penelope attempts to get Nate as her date to the Snowflake Ball, planning with the girls and a reluctant Jenny to humiliate Vanessa. Isabel, Penelope and Nelly Yuki are all present when they plan on declaring Emma Boardman as the new Queen, which went to Jenny. Penelope refuses to have a girl from Brooklyn carry out their legacy but Blair convinces them otherwise. Penelope returns in season 4 as she attends Columbia University. She is currently a member of an exclusive club, the Hamilton House. She also continues to be Blair's loyal right-hand woman, and the ring-leader of her sidekicks. The following season, Penelope competes, alongside Blair's former minions Kati and Jessica, for a spot as Blair's bridesmaid in her upcoming wedding.
Portrayed by Dreama Walker in seasons one and two, Hazel Williams is a member of Blair's clique until she was dethroned as queen bee; constantly shifts her allegiance between Blair and Jenny. Jenny steals her mother's Valentino dress during Jenny's birthday. She forgives her right after Jenny impresses Blair's clique by bringing Nate during their dinner at Butter. Like Penelope, she gives Jenny the benefit of the doubt when Jenny lies about having sex with Asher, eventually breaking her friendship with Jenny. Along with Isabel and Penelope, she succeeds in publicly humiliating Vanessa at the Snowflake Ball. Hazel has tendency to be desperate for a boyfriend and Jenny at one point blackmails her to treat Nelly Yuki better by reminding her that she once hooked up with her cousin. She also regularly checks Gossip Girl's blog and once suffered symptoms of withdrawal when Rachel Carr has cellphones banned from Constance premises.
Portrayed by Yin Chang in seasons one, two and six, Nelly Yuki is Blair's academics rival. Depicted as a bookworm, she's a Merit Scholar, a Peabody Scholar, and an Intel Science Talent Search Finalist. Itzhak Perlman gave her first violin and her parents own a substantial amount of property in Tribeca. Despite being sabotaged by Blair during the SATs, she has a short-lived friendship with her, and sides with Blair (along with Isabel) during Blair's battle for the throne. She also brands Jenny Humphrey a liar, ending Jenny's status as Queen Bee. Nelly is part of Blair's clique in season two. Jenny tries to help her out when she fears the girl is being bullied too much by the other clique members, using Nelly's knowledge to blackmail them into backing off. When Nelly realizes Jenny has no intention of taking over as the new Queen Bee, she reveals she was playing Jenny the whole time to take advantage of a regime change and goes back to the clique. She wins admittance to Yale University over Blair after their long rivalry in the second season. Nelly eventually approves of Jenny becoming Queen at the end of the 2nd season. In Season 5, Nelly, still remaining a student at Yale, is invited to return to tryout to become a bridesmaid at Blair's wedding but doesn't show up because she hates her and is replaced by Charlie instead. In Season 6 episode 2, Nelly Yuki returns as a fashion reporter sent to review Blair's new fashion line. Blair, having bullied Nelly throughout high school, becomes convinced Nelly is working with Poppy Lifton to sabotage her debut and goes to extreme means to stop it only to discover that Nelly just let Blair "implode" as she often does. Nelly also gives Dan advice to stop trying to get into the elite crowd. Nelly later judges Blair's first fashion show, seated next to Serena who assumes Nelly is still one of Blair's minions until the show goes badly, and Nelly writes it up as a disaster. However, she eventually gives a stellar review of Blair's line, contributing to Blair's success in the fashion industry. In Season 6 episode 3, she equivocally displays her affections for Dan at a bar, only to be overlooked for a tall, red-headed woman with whom Dan leaves the bar.
Portrayed by Matt Doyle in seasons two, three and four, Jonathan Whitney is Eric's ex-boyfriend. In "The Goodbye Gossip Girl", Jonathan was mistakenly identified as "Gossip Girl" when the presiding room was silenced and Serena texted her,"Now I know who you are." It turns out that he had hacked Gossip Girl's website. In season three, Jonathan was absent for a few episodes - he was with his grandparents - when he returned, he and Eric challenged Jenny's authority over the school by sitting higher on "the steps" than her and her cronies, this resulted in Eric being splattered with yogurt. That night, at a party, ("They Shoot Humphreys, Don't They?") Jonathan is egged by Jenny's cronies, angering Eric, who plots to ruin Jenny's Cotillion. But when Jonathan learns of Eric's scheming with Blair, he breaks up with him. In season four, Jonathan tries (unsuccessfully) to reconcile with Eric.
Portrayed by Elizabeth Hurley in season five, Diana Payne is a sexy, smart, and manipulative cougar. She first meets Nate Archibald in Los Angeles at a party at her home (while Nate claims the house is his) and end up in bed together. She soon ends up in New York and launches her own online journals: 'The NY Spectator.' We next find out her goal is to take down the infamous blog and media social rumor site in New York - 'Gossip Girl.' Until their secret relationship reaches its breaking point, Nate and Diana find themselves attempting to make each other jealous until Diana decides to go public - via the NY Spectator. Meanwhile, Diana finds out the story of Ivy and Charlie being the same person and forces Charlie to work for her and threatening Ivy Dickens's life. At the end, more shocking twists are revealed as the evil Diana and Nate's crooked grandfather, William van der Bilt, are revealed to have been working together to orchestrate Nate's employment with Diana as part of sinister grand plan for Nate and then she is gone out of town. In episode 19 "It Girl Interrupted" Diana Payne's return to The Spectator starts a power struggle with Nate and Diana meets Nate's new girlfriend, Lola Rhodes. After her return, Lola inadvertently reveals to everyone that Diana is Chuck's biological mother. Trying to find more information about her, Nate finds that Diana Payne may not be her real name.
Portrayed by Kevin Zegers in seasons three and four, Damien Dalgaard is a drug dealer and the son of the Belgian ambassador. Later befriends Jenny and uses her as a drug mule and gets her to become a dealer. He begins dating Jenny and wanted to have sex with her, and when she refused he left her. It was revealed in "The Hurt Locket" that he was very intelligent and athletic, and also went to the same boarding school as Serena when she went away. Later on, this is also reaffirmed in "The Townie".
In season 4, Damien tries to help Blair and Dan find Juliet when he finds out that he sold Juliet a large amount of drugs such as cocaine, pills and ether which was used to drug Serena. At one time, he started to sell sleeping pills to Eric. To get revenge on Ben, when the latter has threatened him to stay away from Serena and her family, he befriends Eric and comes up with a scheme to send Ben back to jail, unsuccessfully. As he has used Eric for his intent, he ends his fake friendship with Eric. Dan and Nate, thinking that Eric is in the embassy with Damien, went for him. They did not find them but they have found the ambassador. They told him his son is a drug dealer and he was cut off from his father inheritance. He starts to blackmail Eric with the information he knows about the affidavit Lily forged against Ben. Eric was to deal drugs for Damien, so that the latter could keep a low profile with his father. Damien has acquired a check of $100,000 by Eric. As he exits the Van der Woodsens' building he was stopped and death threatened by Ben to stay away from the Van der Woodsens while gaining the check back.
Portrayed by Hugo Becker in seasons four and five, Louis is the heir to the throne of the principality of Monaco. He meets Blair in Paris at the beginning of season four and begins to fall for her - however, not wanting her to be only interested in him because of his title, he acts as if he is a chauffeur (though Blair later discovers the truth). Blair turns down Louis both to return to Manhattan and because she isn't over Chuck, giving him her shoe so he can find her again. At the end of the season, Louis comes to New York to woo Blair. Blair tells him that she wants a relationship and at first they meet secretly so Louis' mother doesn't discover her son is dating a commoner. Louis asks Blair to marry him after she runs away from a royal event Chuck ruined with his drunken declarations of love, though his mother doesn't think Blair is suited to be a princess of Monaco. Later, with the help of Cyrus, Louis' mother is convinced Blair is worthy enough, and in deference Louis often upholds her wishes over Blair's. Louis, while usually mild-mannered, is intensely paranoid about Blair's previous relationship with Chuck, who often has to cajole him into returning to and trusting her. In Season 5 episode 13, the 100th episode, Louis and Blair's wedding ceremony was interrupted by an explosive Gossip Girl blast, a video of Blair professing her undying love for Chuck, not Louis. Afterwards, Louis forgives Blair and continues the ceremony. However, at the reception, Louis reveals to Blair that the wedding stands as a contract and "a show", but that their love does not exist.
Portrayed by Katie Cassidy in season four, Juliet Sharp is an intriguing woman that Nate first met in a bar while he's on a date with one of the girls of Chuck's little black book. She knows much more about the gang than what she lets on, and she's the one who advises Vanessa to get back together with Dan, so that Nate can get Serena back. At the end of the third episode, she meets a man in prison, Ben, who is later found out to be her brother. When Nate begins to suspect Juliet's strange behaviour and busy schedule, he asks her to tell him more about her life. She takes him to what appears to be her apartment, but while Nate goes to see the place, she hands some cash to a man who tells that the real owners of the apartment will be back in the next day. Her glamorous, impenetrable façade and dismissive approach to love actually hides a sensitive, caring nature and as the season progresses, she declares to having genuine feelings for Nate. But after her brother attacks Nate's father in jail for Juliet's attempt at forgoing their plans, she calls Nate, and ends their relationship for the sake of Howard's safety. After she hangs up, Serena's professor Colin then enters the room and hands Juliet a cheque, thus making us believe that he is in on her plan to sabotage Serena. We later learn that he is in fact her cousin, and that the cheque was to cover her rent and school fees, he has no idea of her and her brother's plans for Serena. Juliet, Vanessa, and Jenny come together to strike a savage blow against Serena, landing her a place at the Ostroff Center for recovery. Juliet proceeds to blackmail Lily for a monthly cheque by telling that she will reveal one of Serena's other dirty secrets if she does not provide her with cash. To avoid the wrath of Blair and others, Juliet leaves to return to her home town. A while later, Juliet sees Damien, Dan, and Blair getting into a car together, making her assume that they know all about what she's done and bringing her back to Manhattan to tell Serena everything. Serena and Juliet make peace when Juliet finds out that it was really Lily who signed the document that caused her brother sentenced five years in prison. Before she departs for her home town once more, Juliet promises not to cause harm to Serena or anyone else again. However, this does not convince Nate, who rebukes her. This hurts Juliet immensely as she leaves.
Portrayed by David Call in season four, Ben Donovan is Juliet's brother who is in jail. He was Serena's English teacher for a brief time, and having spent some time together they both developed mutual feelings. When Serena returned to Manhattan, Ben was charged with statutory rape and transporting a minor across state lines. A crime of which was signed off by with Serena's very own signature. This caused him to be forced into serving a five-year sentence for a crime that he did not commit. He and Juliet devised a plot to destroy Serena's life permanently, however with no real intent on hurting her physically. In the end it was revealed that Lily, Serena's mother, had him put in jail by faking her daughter's signature so that Serena could return to Constance,
Serena visits Ben to explain everything and to successfully attempt a reconciliation. Ben and Serena started to hang out, later developing into a couple. He has threatened Damien to stay away from the Van Der Woodsens twice, the second being a death threat.
Portrayed by Michael Boatman in season four, Russell Thorpe is a longtime friend of Bart Bass who started in the real estate market around the same time together. After Bart stole most of his deals and wrecked many of his business plans, Thorpe essentially was run out of town and went to Chicago to build his own empire there. Russell and his daughter Raina returned to the Upper East Side in The Kids Are Not Alright to shake things up for the reigning families and buy Bass Industries. Morever, he and Lily also shared a sexual past, although she states that it was a very long time ago. He is against the relationship between Raina and Chuck.
Portrayed by Tika Sumpter in season four, Raina Thorpe is Russell Thorpe's savvy and candid daughter who also assists her father in his business dealings. Chuck Bass first meets her and assumes that she is his assistant, to which she says that she is his secretary. Later, he finds out that she is in fact his daughter and the vice-president of her father's company. She is involved with her father in buying Bass Industries and later admits to Chuck that it was Russell who tipped off a potential buyer so they could acquire it. She also offers to sleep with Chuck, who takes her up on the offer at the end of "The Kids Are Not Alright". They have a short sexual relationship which ends when Chuck is told by Russell that Bart Bass was responsible for the death of Raina's mother, Avery. He explained that Bart was having an affair with Avery over twenty years ago, and that Bart purposefully trapped her in an apartment fire when she decided to go back to Russell. He tells Chuck that he has led Raina to believe that her mother abandoned them when she was a baby, so she doesn't know about her death. "In Damien Darko", Chuck asks Raina to get Nate's father fired after finding out that he is working for Russell Thorpe. She later develops a romantic relationship with Nate, who tells her the truth about her mother. She tells Russell she wants nothing to do with him, but later helps Blair and Chuck when it's discovered that he was responsible for killing her mother.
Reed Birney portrays Mr. Prescott in seasons one and two, a teacher at Constance Billard and St. Judes. Jill Flint portrays Bex Simon in seasons one and two, Lily's art dealer and a minor love interest for Rufus. Alison Humphrey, Rufus' ex-wife and Dan and Jenny's mother is portrayed in season one by Susie Misner. Mädchen Amick portrays Duchess Catherine Beaton in the second season. She has a short affair with Nate. Her stepson, Lord Marcus Beaton is portrayed by Patrick Heusinger in season two. He has a relationship with Blair. At first he pretends to be a college student called James, but when Blair thinks he is boring, he tells her the truth. When Blair finds out that he is having an affair with his stepmother, she blackmails them into leaving the country. Tamara Feldman portrayed Poppy Lifton in the second and sixth seasons, a friend of Serena's. Her boyfriend, Gabriel Edwards, is portrayed by Armie Hammer in the second season. When Serena comes back from a holiday in Spain with Poppy and Gabriel, she starts a relationship with him. However Poppy and Gabriel are actually still together and use Serena to steal money from Lily. John Patrick Amedori portrays Aaron Rose in season two, an artist who becomes a love interest for Serena. However she leaves him when she realizes she still likes Dan. Willa Holland portrays Agnes Andrews in season two and for one episode in season three. She is a model that befriends Jenny, however when the two become business partners, things go wrong and they become enemies. Andrew Tyler, a detective that works for Bart and Chuck, is portrayed by Kevin Stapleton in seasons two and four. Aaron Schwartz portrays Vanya in seasons two, three and four, the doorman at the building of LIly's apartment, who later marries Dorota. He and Dorota have a daughter in season three and are currently expecting a second child. Laura Breckenridge plays Rachel Carr, Dan's romantic love interest and his teacher in Season-2
Joanna Garcia portrays Bree Buckley in the first four episodes of season three. Her and Nate's families are rivals and they begin a "Romeo and Juliet" kind of relationship. When she finds out that her cousin is left at the altar at her wedding to Carter Baizen, she tries to get revenge on him for her family, which leads to her and Nate's break-up. Olivia Burke is portrayed by Hilary Duff in season three. She is a famous movie star that starts a relationship with Dan. They break up when she realizes Dan has feelings for Vanessa. Deanna Russo portrays K.C. Cunningham, Olivia Burke's publicist and Serena's former boss, in season three and for one episode in season four. Laura Harring portrays Elizabeth Fisher in season three. She's Chuck's mother, who was thought to have died when giving birth to Chuck. She reveals to Chuck that she left when he was born, because she was nineteen and had no intentions of marrying Bart. Bart later paid her to stay away from their son. She also dated Chuck's uncle Jack in the past, who she gave Chuck's company to after he had given it to her. Sherri Saum portrays Holland Kemble in season three. She is hired by William van der Woodsen to seduce Rufus in order to break up him and Lily. Luke Kleintank portrays Elliot Leichter, Eric's bisexual love interest, in seasons three and four. Jessica, portrayed by Alice Callahan in seasons three, four and five, is one of Blair's new minions at Columbia.
Clémence Poésy portrays Eva Coupeau in the first four episodes of season four. She saved Chuck from dying when he was shot in Prague. They start a relationship and she changes Chuck into a better more philanthropic person. When Blair tries to break them up, she finds out that Eva was a prostitute, but Chuck forgives Eva for not telling him and dedicates a charity in Eva's name. However Eva dumps Chuck when, after all the good things she has done for him, Chuck is still duped by one of Blaire's devious schemes into thinking Eva was only using him. Chuck realizes the error only too late as Eva, heartbroken at Chuck's distrust, flies back to France. Dean Reuther, the dean of Columbia, is portrayed by Jayne Atkinson in season four. Samuel Page portrays Colin Forrester in season four, Juliet's cousin and Serena's college teacher, who she has a short relationship with. Carol Rhodes, portrayed by Sheila Kelley in seasons four and five, is Lily's sister who comes to New York with Ivy, who pretends to be her daughter Charlie, in order to get access to Charlie's trust fund. Brian J. Smith portrays Max Harding in season five, Ivy's ex-boyfriend, who finds out that she is pretending to be someone else and blackmails her. Jane, portrayed by Michael Michele in season five, is a movie producer that hires Serena, but she soon quits. Marina Squerciati portrays Alessandra Steele in season five, a publicist that publishes Dan's book.
During season five, Roxane Mesquida portrays Béatrice Grimaldi, Louis' sister who doesn't approve of her brother's interest in Blair. Marc Menard portrays Father Cavalia, a priest from Monaco with ties to Blair’s fiancé, Louis. Amanda Perez as Tina, Nate's assistant at The Spectator.
Special cameo appearance
- The Pierces ("Hi, Society")
- Lisa Loeb ("Woman on the Verge", "New York, I Love You XOXO")
- Sylvia Weinstock ("Woman on the Verge", "Rhodes to Perdition")
- Ebony J Lewis ("Much 'I Do' About Nothing")
- Tinsley Mortimer ("Summer Kind of Wonderful", "The Serena Also Rises")
- Cristina Greeven Cuomo ("The Serena Also Rises")
- Michael Kors ("The Serena Also Rises")
- Honor Brodie ("Chuck in Real Life")
- Ariel Foxman ("Chuck in Real Life")
- Cyndi Lauper ("Bonfire of the Vanity")
- Nastia Liukin ("It's a Wonderful Lie")
- Charles Isherwood ("The Age of Dissonance")
- Patrick McMullan ("Remains of the J")
- Ashley Hinshaw ("Reversals of Fortune")
- Nacho Figueras ("Reversals of Fortune")
- Alexandra Richards ("Reversals of Fortune")
- Sean MacPherson ("The Lost Boy")
- Tory Burch ("Dan de Fleurette")
- Tyra Banks ("Dan de Fleurette")
- Georgina Chapman ("Dan de Fleurette")
- Kim Gordon ("Rufus Getting Married")
- Jimmy Fallon ("The Grandfather: Part II")
- Plastiscines ("They Shoot Humphreys, Don't They?")
- Lady Gaga ("The Last Days of Disco Stick")
- Alexandra Carl ("The Hurt Locket")
- Deadmau5 ("The Empire Strikes Jack")
- Lou Doillon ("Belles de Jour")
- Karlie Kloss ("Belles de Jour")
- Willy Wong ("Belles de Jour")
- Danielle Billinkoff ("Belles de Jour")
- Meredith Melling Burke ("Belles de Jour")
- Hamish Bowles ("The Undergraduates")
- Charlotte Ronson ("The Undergraduates")
- Diane von Fürstenberg ("The Undergraduates")
- Alessandra Ambrosio ("The Undergraduates")
- Kick Kennedy ("Touch of Eva")
- Tim Gunn ("Easy J")
- Jared Kushner ("Easy J")
- Isaac Mizrahi ("Easy J")
- Ivanka Trump ("Easy J")
- Cynthia Rowley ("War at the Roses")
- Joe Zee ("War at the Roses")
- Rachel Zoe ("War at the Roses")
- Robyn ("War at the Roses")
- Darci Kistler ("Juliet Doesn't Live Here Anymore")
- Peter Martins ("Juliet Doesn't Live Here Anymore")
- Gillian Murphy ("Juliet Doesn't Live Here Anymore")
- Ethan Stiefel ("Juliet Doesn't Live Here Anymore")
- John DeLucie ("The Witches of Bushwick")
- Minnie Mortimer ("The Townie")
- Stefano Tonchi ("Damien Darko")
- Robert Ackroyd ("Panic Roommate")
- Florence and the Machine ("Panic Roommate")
- Cecily von Ziegesar ("The Wrong Goodbye")
- David O. Russell ("The Wrong Goodbye")
- Zoë Bell ("Yes, Then Zero")
- Jenny Lewis ("Yes, Then Zero")
- Johnathan Rice ("Yes, Then Zero")
- Sloane Crosley ("Memoirs of an Invisible Dan")
- Elizabeth Quinn Brown ("Rhodes to Perdition")
- Matthew Lynch ("Riding in Town Cars with Boys")
- Vera Wang ("The End of the Affair")
- Dick Cavett ("Con-Heir")
- Bethany Carkhuff ("Gone Maybe Gone")
- Kristen Bell ("New York, I Love You XOXO")
- Rachel Bilson ("New York, I Love You XOXO")
- Michael Bloomberg ("New York, I Love You XOXO")
- Jonathan Karp ("Simon and Schuster- Dan's publisher")
- Ausiello, Michael (May 9, 2011). "Gossip Girl Exclusive: Taylor Momsen and Jessica Szohr Not Returning For Season 5". TV Line.