Alan Harper (Two and a Half Men)
|Alan Jerome Harper|
|Two and a Half Men character|
|Created by||Chuck Lorre|
|Portrayed by||Jon Cryer|
|Nickname(s)||The Sponge by Charlie
Zippy by Berta
Huggy Bear by Kandi
Jeff Strongman by Larry
Member Board of Directors - Walden Loves Alan Enterprises
|Spouse(s)||Judith Harper-Melnick (m. 1991-2004)
Kandi Harper (m. 2006-2007)
|Significant other(s)||Melissa (ex-girlfriend)
Lyndsey MacElroy (ex-fiancée)
|Children||Jake Harper (son)|
Alan Jerome Harper, DC, is a fictional character from the CBS situation comedy Two and a Half Men. Jon Cryer has played the role since the series began in 2003. For his portrayal, Cryer was nominated for a Primetime Emmy Award for his depiction of the character from 2006–2012, winning the award for Outstanding Supporting Actor in a Comedy Series in 2009 and Outstanding Lead Actor in a Comedy Series in 2012.
According to Eric Tannenbaum, executive producer on the show, Alan Harper is loosely based on his real life friend Stephen Deane. As of season 10, Alan is the only character on the show to appear in every episode of the series. At the start of season 11, he became the only original title character.
A main theme of the show is Alan and his brother's contrasting abilities, including his brother's success in dating. Alan is very awkward when it comes to women, and he has had several long-term relationships end badly. This makes him the polar opposite of his brother Charlie, who can get any girl he wants but rarely sees women after he sleeps with them (though he also had some longer relationships conclude in a rather unhappy fashion). Charlie's housekeeper, Berta, described Alan as "the only man who can drive any woman out of Charlie's house." This theory was proven when Charlie was afraid of his attraction to Chelsea's gorgeous friend Gail, and falsely told Alan he had a shot with her; after Alan flirted with Gail, she fled the house in horror and Charlie's temptation was gone.
As a child Alan was often the victim of bullying and got no help from Charlie since his brother participated in much of it. Not much is known about his relationship with their father since he died from food poisoning when they were young, after Evelyn served him spoiled fish that had been stored in a drawer.
Alan used to be married to Judith (Marin Hinkle), the mother of their son Jake; after they divorced, Alan got stuck with paying her $3875 monthly alimony, thus forcing Alan to move in with brother Charlie at the onset of the series. Judith lived a luxurious life on Alan's alimony until she married Dr. Herb Melnick (Ryan Stiles), Jake's pediatrician (also known as Greg Melnick in earlier episodes). Alan was so overjoyed at the end of his alimony requirement that he had a large cardboard check made for her for the last payment. Following the wedding, he only had to pay child support, which Judith does not need but gladly takes from Alan to keep him miserable.
Alan's second wife Kandi (April Bowlby) was one of Charlie's former girlfriends. She was so incredibly stupid she made Jake look like an intellectual. In the divorce, she received the condominium they bought with casino winnings after their impromptu Las Vegas wedding.
Alan went to California State University at Long Beach, but failed to get into medical school. He studied chiropractic in Guadalajara with almost no Spanish language skill. Alan had wanted to be a doctor, but he could not get into medical school, and Evelyn did not help him because she did not think he was worth it.
While he loves his brother and son, Alan resents Charlie somewhat, mostly because everything (money, women) just seems to fall into Charlie's lap, while Alan has worked hard his whole life only to remain a failure and has yet to reap such rewards. (Alan notes at the beginning of Season 8 that just one of Charlie's monthly royalty checks for his children's songs is more than he makes in a year.) Although he and his brother do have a sometimes tense relationship, they remain loyal to one another with Charlie able to cheer Alan up when he needs it, or Alan having to control Charlie's free spending ways when it damages his finances. He has little confidence in Jake, mostly because of the boy's lazy, unmotivated attitude, but he does love his son.
Alan also gets little sympathy even when he's had terrible misfortunes befall him. When he fell off the roof while fixing a satellite dish and was severely injured, he got little sympathy from Charlie, Judith, or Evelyn. He has also had to suffer torments caused by Charlie's behavior. He also got no sympathy after his second divorce.
Generally a nice guy, Alan has displayed some bad behavior and sneaky motives. When Charlie was going to couples-counseling with Chelsea, he fed Charlie a bunch of false information from conversations with her, and Charlie ended up looking like a fool. He has also hidden money from Charlie and once held off on telling Chelsea he was not Charlie when she snuggled next to him on the couch (she thought Charlie had fallen asleep there, but Charlie had forced Alan to give up the guest room and sleep in the TV room instead). Alan hit his low point when his above-board idea to solicit money from all his "family and Friends" in order to finance an ad campaign for his floundering chiropractic clinic slowly turned into a Ponzi Scheme. This encouraged him to let his dark side out, although he ended up giving everyone back their original investment and returning to square one.
Because of his cheapness, neurotic nature, and inept social skills, many find Alan annoying, even insufferable—-particularly Charlie, Evelyn, and Berta, who calls him "Zippy." On his 40th birthday, instead of saying nice things about him, everybody pointed out all his faults. Also, Jake seems to have little respect for him, though Jake is not particularly respectful of Charlie or Judith either, and is not generally rude when he talks to his dad. Though Evelyn has called him the good child, she added that Charlie had not set that bar very high. She also once seriously suggested he accept some prison time after an assault charge because she wanted to save money instead of using it to hire a lawyer. This leaves Alan with very few (If any) friends.
It is also implied that in the universe of the series that God himself has a dislike for Alan, for example when Charlie told Alan reminded him of Job, Alan shouts to the sky that he is not going to lose his faith only to start raining a few seconds later. The same thing happens in "Pie Hole, Herb" when Charlie refuses to take Alan back in (having kicked him out earlier), locking him out of house.
Alan is also seen as pitiful when he tries activities such as model car building and puppetry, because it highlights how anemic his social life is.
Alan drives a 2001 Volvo V70 station wagon (though he briefly owned a red Porsche Boxster in Season 2), runs his own chiropractic-care clinic in the San Fernando Valley, and gets irritated when people point out that he's not a "real" doctor. He lives in the guest room of Charlie's house, for which he paid no rent during his first 5 years, 2 months, and 11 days there because all his money went toward alimony and care of Jake. When Evelyn said she would pay for Jake's college education, Alan had no incentive to go to work and felt aimless. He then agreed to pay rent to Charlie every month, though the amount that would earn him a say in the household's operations was too high for him. Alan has also had to endure whatever inconvenience Charlie throws his way, and the fact that Charlie really, really wants him to move out permanently. Alan has also sometimes fantasized about killing Charlie in his sleep.
Alan is also a terrible liar, as proven in several episodes where he hastily creates a lie to get out of doing something, and Charlie always asks him for more detail to torture him and expose the lie.
Judith is Alan's first wife and Jake's mother. She is generally portrayed as humorless, bitter, and hypocritical. Judith told Alan that the reason they were separating was because it was not working out, but then later told Alan that she had realized she was a lesbian, only to change her mind again later. While she sees herself as lonely and long suffering, Judith is actually quite cruel, spiteful, vindictive, irrational, unfriendly and selfish. According to Alan, Judith was a thin, scared, needy and neurotic mess with a strange eating disorder when he met her, and lived in the shadow of her more attractive popular sister. This could explain why she grew into such a bitter, angry, hate-filled person.
Alan and Judith met as teenagers and married young, though Charlie and "everybody else" advised Alan against marrying Judith. He lost his virginity to her during an Aerosmith song (from the episode "Who Is This Vod Kanockers?"). During the separation, Alan desperately tried to reunite with Judith, not realizing that the real reason she kept calling him and asking him to rush over was simply to keep him doing the chores he always did around their home. Judith clearly depises him and takes every chance to make his life miserable, even though it is sometimes clear that Alan and Judith still have feelings for each other. Once she said: "I disliked you when we were married, I resented you when we divorced, but I don't think I hated you until you started having sex with that gorgeous, 22-year-old dumbbell." Judith also felt sorry for Alan after his second divorce to Kandi, though she made it clear that she would not give him any breaks on alimony even if he had to pay that to Kandi as well. (She also arranged for the lawyer who decimated Alan in their divorce settlement to represent Kandi, though it appeared that Alan's financial losses there occurred before Kandi left him.) In a Season 5 episode, Alan begins dating a divorced woman who is friends with him and Judith, but keeps having visions of Judith and Herb having sexual intercourse, leading his date to say that he's not over Judith. Alan and Judith tried dating again in Season 3, which was after the divorce, but their attempts at intimacy were always interrupted by Jake approaching and Alan having to hide. Then when they finally had some uninterrupted time alone, Alan got upset because Judith had learned some "new moves." As they fight about this, Jake approaches and Alan jumps out the second-story window and lands in a thorny bush. At home, he finally realizes that he and Judith do not belong together.
Before the divorce, Alan actually thought he and Judith were on their way to reconciliation until he was served divorce papers in the mail.
One time (though it might have been intended as a joke to the audience), it was strongly implied that Jake might not be Alan's son, since he bears a strong resemblance to three long time acquaintances of Judith and Alan who were all in dead-end jobs (exterminator, water man and postman). While it was probably a joke, given Judith's attitude towards Alan, it's not an unlikely scenario. However given Jake's recent misfortunes with girls, he seems destined to have his father's luck.
Alan has even tried to be friends with Judith; however it was extremely difficult for him to be happy for the woman who ruined his life.
Judith has accused Alan of being controlling, but it's clear that she dominated the marriage while Alan bent over backwards trying to make her happy. Her relationships with her parents and sister are not much better; her mother is a longtime alcoholic and prescription pill abuser; she's called both parents "poison"; and she argues with her sister constantly. Judith has little tolerance for people she does not like; she was cruel to her future sister-in-law; and her first words whenever Alan comes to her house are either "What are you doing here?" or "I swear to God, you're worthless."
During the divorce proceedings, Alan had (and continues to) suffered greatly. He lost most of his possessions after Charlie slept with his attorney (Heather Locklear), then broke up with her, forcing him to fire her before the settlement could be finalized. When Judith hires her, she does everything in her power to crush Alan in the settlement (why Alan was bound to the grossly unfair terms that the attorney inflicted on him due to Charlie's behavior was never explained). Even after the divorce, Alan is constantly at Judith's mercy because of her powerful lawyer. Judith gets remarried in "Smooth As A Ken Doll" to Dr. Herb Melnick, Jake's pediatrician. Since that day, Alan may only be paying alimony to his second wife Kandi, a relief since there was some time before Judith remarried that he had to pay it to both Judith and Kandi. It is possible Alan does not pay Kandi alimony because she now makes much more money than he does, and that she signed divorce papers because she wanted to safeguard her earnings from Alan.
While Judith blames Alan and Charlie for a lot of Jake's shortcomings, she herself seems to have little faith in him and far less patience, as she takes any chance she can to drop him with Alan at Charlie's house. In Jake's Final Episode, Jake told Alan the Divorce was never fault and all Judith's. This showed that even her own son couldn't deny she was a hopelessly miserable woman.
In Season 6, Judith threw Herb out of their house and later slept with Alan, but their reconciliation ended when Alan realized Judith was the same angry, irrational person who had divorced him. Judith later told Alan that she and Herb were expecting a child, leaving a horrified Alan to think he might be the biological father. His fears were assuaged when Judith stated that Herb was the father and threatened to kill Alan if he revealed their affair. Judith does not like the fact that her daughter looks just like Alan, but Alan seems to enjoy pointing it out to her.
Despite saying she loves Herb, Judith seems to treat him in the same cruel and unfair way she treated Alan. Judith's parents seem to prefer Alan to Herb although Herb is a "real" doctor — but they also prefer Alan over Judith. Herb and Alan are great friends, but Judith disapproves, so Herb has to lie to her in order to hang out with Alan and/or Charlie. Over the course of the show, Alan and Judith's mutual hatred increases to the point that one will do anything to upset the other. When he could not afford a nice birthday present for his girlfriend Lyndsey, Alan stole earrings from Judith's house that he'd gotten for her when they were married, and after getting away with it, he decided to steal a nice necklace from Judith as well.
Recently, Judith has left Herb. She has yet to reappear.
Alan's second ex-wife Kandi (April Bowlby) was one of Charlie's former girlfriends, whom Charlie originally dated as a backup in case something went wrong between him and his girlfriend Mia. When Kandi came looking for Charlie, who was now more serious about Mia, she met Alan and they fell in love. They married in Las Vegas, shortly before Alan won $500,000. They divorced later, initially because Alan did not want another child.
When Alan changed his mind and decided that he wanted to have children with Kandi, they had not officially signed their divorce papers. Kandi then heard that she had a main role on the TV series Stiffs and said that "nobody wants to see a pregnant 'fornesic' investigator" before signing the papers that ended their marriage. Their married life was never shown in episodes, inferred to have lasted only between the end of the third season and beginning of the fourth. Early in Season 4 Alan noted that after they bought a condominium, Kandi squandered their remaining Vegas winnings on clothes and shoes. Alan briefly mentioned Kandi in Episode 5 of Season 4 when he tells Charlie that he is paying alimony to two ex-wives. She was not seen or mentioned in Seasons 5-9. When Alan is given the opportunity to talk about his two divorces to Charlie in Season 7's "Captain Terry's Spray-On Hair," he only mentioned his life with Judith. Since Charlie is upset about learning he has not been satisfying Chelsea like he thought he was, and is asking for Alan's advice since Alan is an expert at not satisfying women, it can be inferred that Alan at least had a very happy sex life with Kandi. Kandi returned in the season 10 episode, "I Scream When I Pee", wanting Alan back, but he turned her down for Lyndsey. Lyndsey was happy that Alan chose her, but when Kandi called Alan in the middle of the night, pretending to be suicidal, she came on to him, and paparazzi took photos, which Lyndsey saw. Alan pleaded with Lyndsey that nothing happened, but she didn't believe him. Kandi went to Lyndsey's house and explained everything. Kandi and Lyndsey ended up sleeping together, and agreed Alan must never find out. Walden was shocked that Kandi and Alan were married, and despite being a big fan of Kandi, Alan didn't introduce him to her. Alan and Kandi also did not discuss Charlie's death, despite Charlie being the one who introduced them.
Melissa (Kelly Stables) is Alan's former receptionist. She served as his receptionist for most of season 6 and is shown to have a perky demeanor. Before she dated Alan, she had dated Charlie in "The Flavin And The Mavin," which ended disastrously with her driving angrily and fast in a heavy rainstorm on the way to Alan's office and Alan being forced to give her a raise and health insurance. After recovering from her breakdown, Melissa starts to fall for Alan, but he is also introduced to her mother (Carol Kane), which complicates things---especially after Melissa catches them in bed together in "David Copperfield Slipped Me A Roofie."
Since then, Melissa has been working in the hospital where Judith gave birth in "Baseball Was Better with Steroids" to try to forget about him. However, her feelings for Alan return while Judith is giving birth, and they end up making out in the storage closet. In the season 7 premiere "818-jklpuzo," Melissa appears to have moved into the Harpers' beach house; when Charlie reminds Alan, he is quick to deny it. In "Whipped Unto The Third Generation," Chelsea forces Charlie to let Melissa stay. When Alan and Melissa take advantage of Charlie's generosity, Charlie stays the night at a hotel. Alan is quick to join him when Chelsea and Melissa do not obey his commands. Alan and Charlie turn to Evelyn, who reveals that Melissa and Charlie slept together, making Chelsea and Melissa end their friendship, and Melissa moves out, promising never to return to Charlie's house again.
In the episode "Laxative Tester, Horse Inseminator," Melissa is tired of Alan's cheapness and lack of his own place, so Alan tries to earn some money as Evelyn's assistant. When showing a particularly nice house, Evelyn informs Alan that the couple that own the place have houses all over the country and probably do not even remember this one. Alan promptly invites Melissa to the house that night, telling her he has rented it—but he insists that they have sex on a beach towel on the living-room floor. Inevitably, they spill wine on the floor and Alan makes a fuss because they were not supposed to be there. They are then forced to flee in their underwear when Evelyn arrives with potential buyers, and when the cops catch them, Melissa abandons Alan to deal with them. It is implied that this incident broke them up; in Alan's words: "You could say I dumped Melissa, and decided she never wants to see me again for as long as she lives."
Alan has since gone on other dates, including one with a grossly overweight woman whom he takes to an L.A. Dodgers game; another ended with him boring his date, then punching out the rude jerk who was successfully getting her to go off with him. Near Season 7's end, he begins dating Lyndsey (Courtney Thorne-Smith), the divorced mother of Jake's best friend. Hours after moving in with Lyndsey, however, Alan bumps into Melissa at a liquor store and the two dash back to his old bedroom at Charlie's house. Alan tells Charlie that he still wants to live with Lyndsey, but that he and Melissa have "so much chemistry" he wants to keep Melissa on the side. After a few days of vigorous sex with Melissa which tends to leave Alan unable to perform with Lyndsey, Melissa discovers that Alan is two-timing and she leaves him again.
Near the seventh season's end, Alan meets a personable divorced mother named Lyndsey MacElroy (Courtney Thorne-Smith). She lives across the street from Judith and Herb; the neighborhood men are happily aware that she was once featured in a soft-core pornographic movie. Thanks to Herb, Charlie has also enjoyed the film, although Alan remains oblivious. Her son Eldridge (Graham Patrick Martin) is Jake's classmate and friend and appears to be his intellectual equal. Lyndsey and Alan have at least two Alan-Harper-style sexual encounters: one in the bathroom of a local bar, and the other at a hotel where she suffers through a bad menstrual period. During the interim between seasons 7 and 8, their relationship grows significantly. Alan moves in with Lyndsey at her insistence, although he's reluctant to lose his freedom and Jake resents losing his (uncle's) weekend beach house; after Charlie's repeated attempts to make Alan "uncomfortable" after he says "My relationship with Lyndsey is fine the way it is." But Charlie wants him to move out so his first try is sticking a Parrot named "Larry Bird" in his room. The next morning Alan claims the bird tried to recircumcise him. (it bites penises and Charlie did it because Alan has to urinate at night and the Bird went in after him) the following day Alan is taking a shower and Charlie gets in behind him to creep him out; but once Judith rants about how furious she'd be if Alan became her new neighbor, Alan decides "So I'm moving in with Lyndsey". Lyndsey appears to be notoriously difficult to please sexually, and Alan finds his cunnilingus skills are usually inadequate to bring her to orgasm. At the end of "A Pudding Filled Cactus", Alan's failure to extinguish Lyndsey's late grandfather's tobacco pipe causes him to burn down her house - the second time in the series that Alan's carelessness has caused a fire, after a mishap with a candle in "That Special Tug". This forces the couple and their sons to return to Charlie's house, leaving Lyndsey replete with disgust and resentment toward Alan. Intending to retrieve a drunken and sorrowful Alan from the charred remains of their home, Lyndsey is reunited with her ex-husband, Eldridge's father, Chris MacElroy (Judd Nelson); Chris convinces her to join him for coffee and talk about giving their relationship one more try. But in the episode "A Good Time in Central Africa," Alan gets a call from Lyndsey: she and Chris were unable to reconcile, so she wants to date Alan again. This earns Alan his very own veiled-threat-making stalker in Chris. Then Lyndsey started getting friendly with Charlie, so Alan jealously started spying on them and seemed to have destroyed their relationship anew, although the premature end of Season 8 left this story unresolved. (It was later revealed that an abandoned Season 8 storyline would have been Charlie waking up in bed with a man who was a friend of Lyndsey's, hinting that she may have returned.) Lyndsey reappeared in Season 9, and dated Alan for a few more episodes until she broke up with him after learning that he'd partied while high with a group of girls in bikinis. Lindsey apparently had another boyfriend, a very young, handsome and successful guy named Dylan. However, she broke up with him and reconciled with Alan, telling him that Alan doesn't care about her looks or bodily functions and isn't going to be able to find anyone else anyway. Alan told Jake that he and Lyndsey have absolutely no intentions of getting married. Lyndsey and Zoey (Walden's girlfriend) initially had a very strong hate for one another, but later became friends when Walden and Alan were facing a crisis in a massive rainstorm to get away from the tension in the house. They become engaged in season ten episode "Something My Gynecologist Said" however she sleeps with Alan's second ex-wife Kandi in "I Scream When I Pee". They break up at the end of season ten when Lyndsey thinks the spark in their relationship is gone.
Possible second child
In Season 6, much like she did with Alan, Judith kicked Herb out, which delighted Alan because for years she blamed everything wrong with their marriage on him. Alan went to go see Judith, who started crying because Herb had moved out (though in reality she kicked him out) and Alan (understandably) took great joy in basking in her misery, much in the way she enjoyed his. However in trying to cheer her up, Alan and Judith wound up having sex. While it seemed they might patch things up, their mutual disdain for one another came to light again and Judith kicked Alan out and took Herb back. Six weeks later Judith and Herb announced they were having a baby, leaving a horrified Alan to ponder the fact that HE might be the father. Alan tried to talk to Judith about it, but she cruelly and irrationally denied they ever had sex, and said she'd kill Alan if he ever told Herb, leaving Alan at a loss of what to do about it. Judith gave birth to a baby girl named Milly (with Charlie at her side). While it remains unconfirmed, it seems clear to most people (Charlie, Berta, and even Jake), but not Herb, that Alan is in fact the father because of Milly's likeness to him. Because of Judith's hatred of Alan, she refuses to let him have anything to do with her. Alan's mother Evelyn does not know Milly could be her granddaughter, nor does Alan want her to know, as she will most likely try to stick her nose into and further complicate the matter. Charlie tells Alan not to get involved because it will most likely cause further hate and discontent between him and Judith and ruin Milly's life.
In Season 7's "Mmm, fish. Yum.", Alan took care of Milly (and her intoxicated grandmother) while Judith and Herb took a "romantic getaway." After this episode, Milly had not been mentioned by Alan, Charlie or Jake until season 8, when Herb says he "just put Milly to sleep". Alan had not been seen thinking about the possibility of Milly being his daughter, nor did he ask any questions about her to Judith and Herb.
The topic of a possible daughter is revisited during season 9. In "A Giant Cat Holding a Churro," Alan and Lyndsey tell each other their secrets, with this being one of them. Four episodes later, during "Frodo's Headshots," Walden notes that Judith and Herb's baby looks like Alan, with Herb agreeing and looking puzzled. Herb later meets Alan and says that he did a DNA test which proved that he (Herb) was not the father and that Alan was. Herb then shoots Alan, which causes Alan to wake up in hospital realizing the whole thing had been a dream and remembering that Herb remains unaware of Milly's possible parentage in real life.
Charlie's death and friendship with Walden Schmidt
At Charlie's funeral, Alan is the only person who tries to say something positive about his late brother. Alan, Evelyn and Berta are shown to be the only people saddened over Charlie's death, though Evelyn continuously mentions how she intends on making money from selling his house. Alan expects to get the house, as it was left to him in Charlie's will, and hopes selling it will yield him a significant amount of money. However, continuing on the theme that nothing goes right for Alan, Evelyn informs him that after paying for closing costs, Charlie's three mortgages and her commission, he will be lucky to break even on the deal.
A grief-stricken Alan speaks to Charlie's ashes and tells him how much he loves him and will truly miss him. He also thanks him for allowing him and Jake to move in with him when they had no place else to go. However, Alan accidentally spills the ashes after being frightened by the sight of Walden Schmidt, who was peering in through the window.
Following this incident, Alan listens to Walden talking to his ex-wife Bridget Schmidt (Judy Greer) on the phone, during which it is revealed that a heartbroken Walden tried unsuccessfully to kill himself. Alan learns that Walden is a billionaire, and figuring he can exploit his wealth, he takes Walden for a drink. He and Alan pick up two women and take them home, but both women end up having sex with Walden. Walden subsequently buys the house. After Alan reluctantly moves back in with his mother, Evelyn, a lonely Walden visits to drop off a book Alan left behind and the two end up going out. Alan ends up staying at Charlie's old house with Walden and covers for him when Bridget stops by while Walden is flirting with a girl. A grateful Walden lets Alan stay at the house temporarily, although Alan intends for it to be permanent. However, when Sylvia (Jenny McCarthy), a former flame of Charlie's and nemesis to Evelyn, tries to con Walden out of his money, Alan calls Bridget and exposes her true intentions to Walden. In gratitude, Walden tells Alan he wants him to stay at the house, as Alan has done him a service twice now. Their friendship significantly grows in later episodes. When Walden considers moving to New York at one point, he decides to stay at the beach house in Mailibu because as Walden states, "How could I leave behind my best friend?"
Later on, Walden donates Charlie's piano to a music school, causing Alan to have an emotional and mental breakdown, which progresses to the point where he comes to believe he is actually Charlie by adopting his mannerisms and dressing like him. Walden then has Alan committed to a "relaxation facility" so his friend could regain his sanity.
When Walden first begins dating Zoey, he removes his expensive wedding ring and gives it to Alan; while it appears at first that the perennially destitute Alan has pawned the ring to pay his debts, he keeps it and gives it back to Walden when Walden requests it, only to watch in horror as Walden then throws the ring into the ocean. Walden says he would give Alan money, but Alan decides that he will keep living at the house and maintain the illusion that not taking money from Walden will keep some of his dignity intact. Alan has also says that Walden's renovation of the house has ended any real ties Alan had to it from when Charlie was alive, but it seems like Alan will stay there anyway, because both because of his friendship with Walden and the fact that he has nowhere else for him to go.
On Christmas, Alan is alone on the first holiday without his brother. Jake hangs out with Eldridge, and Evelyn has an orgy with two men instead of spending time with Alan and remembering Charlie. When Walden is upset after learning that his adoptive brother (a gorilla) has been sent away when he was a boy, Alan consoles him by telling him he knows the feeling of losing a brother.
Reunion with Charlie
In the episode "Why We Gave Up Women", Charlie and Alan are reunited when he visits Alan in the hospital, while Alan is being treated for a mild heart attack. However, his soul is trapped inside the body of a woman (Kathy Bates). Initially, Alan is greatly offended at this this stranger impersonating his dead brother, but the woman correctly answers questions that only the real Charlie could do. Having convinced Alan, Charlie explains that he went Hell, and as his eternal punishment it was placed into a woman, due to his womanizing ways during his lifetime. Charlie says his real reason for coming back was to encourage Alan to finally be self-sufficient, and to cease freeloading off of everyone in his life, mainly Lyndsey and Walden. After Alan moves out of the beach house and finds a seedy apartment, Charlie reveals that he couldn't care less what Alan does, all he wanted was to finally get him out of his house. Charlie later tries to reveal himself to Jake but Jake can't pick up on the clues he drops. Irritated, Charlie goes back to Hell.
In the season 11 premiere, Charlie's illegitimate daughter Jenny appears looking for her father, and displays traits of her father, much to the delight of Evelyn and Berta, but to the frustration of Alan. Alan is annoyed to learn that Jenny got big checks from Charlie every month, even though he never lent a penny to his brother.
A major point of humor regarding Alan in the series is that he is notoriously cheap. Many of Charlie's insults and jibes at Alan were usually references to his incredible unwillingness to make the slightest expenditure. He gets his hair cut at a barber college, sneaks deviled eggs into the movies (which Charlie described the smell as "a big box of ass"), and constantly tries to avoid checks in restaurants by going to the bathroom when it arrives, leading Charlie to call it "the little cheap bastard's room". In one episode Charlie joined him in the men's room to make sure he returns and pays his half of a check; Alan procrastinates for so long that their ladies and the check were picked up by Geraldo Rivera. He finds out in the same episode that Alan's constant scrounging was a result of him saving every spare dollar he had for his lonely future as "Old Alan," and he had accumulated over $5,000 in cash.
In later seasons his extreme tightness becomes even more apparent, despite the fact that his financial situation seems to have improved on paper (he no longer pays alimony, Evelyn pledged that she would cover all of the expenses if Jake miraculously got into college, and he remains a rent-free resident at the beach house), and the jokes about his stinginess become more frequent. In season 7 when Alan pays for a meal for himself, Jake and Charlie, Charlie is so astonished that he photographs the event on his iPhone and comments on Alan's wallet opening for the first time.
In one episode, while at the movies, Alan orders $25 worth of food for Jake, only to tell Charlie, that he "forgot" his wallet. This leads to an argument where Charlie complains that Alan said he would pay for parking, which he is unable to do, because he does not have his wallet. After a line builds up because of their arguing, Charlie agrees to pay the bill, as soon as Charlie brings out his wallet, Alan orders a bagel-dog to "make it an even 30.". In season 9, Alan does exactly the same thing to Walden when they go to the movies.
When Melissa refuses to return to Charlie's house after Chelsea calls her a tramp for sleeping with Charlie, Alan resorts to dogging as he refuses to pay for a hotel. Melissa leaves angrily to walk home, commenting that it was not far considering Alan did not want to waste gasoline. (Alan revealed in "I Found Your Mustache" that he fuels up with $3 worth of gas at a time.)
In the episode "Pie Hole, Herb" Charlie borrowed 38 dollars from Alan. Alan is so intent on getting every penny back that he resorts to stealing gasoline from Charlie's car. But since there was not enough gas in the tank, Alan points out that Charlie still owes him 24 dollars and 78 cents.
In "Sir Lancelot's Litter Box" Charlie bribes Alan at first with 20 dollars to make him shut up about his relationship with Chelsea, when he still wouldn't leave, Charlie gave him forty dollars to which Alan initially took but a few seconds later gave the money back until Charlie told he only gave back a twenty dollar bill instead of the forty.
In the season eight episode "Skunk, Dog Crap and Ketchup" when Charlie and Lyndsey were having a night chat Lindsey stated that Alan was too cheap to pay for a prostitute.
Another reason for Alan's cheapness is that his chiroparactic practice has not been consistently successful, mixing periods where he has a high volume of patients with times when he has none of them. When Alan learned that an old friend and colleague living in the same area had a thriving one-man chiropractic clinic, he decided to emulate him by raising money for an advertising campaign, but ended up running a Ponzi scheme where all of his ill-gotten gains went towards luxury items for himself.
If Alan sees that anything is on offer for free he is usually very quick to be interested. When Chelsea's father takes Charlie out for drinks and exclaims that he's buying within earshot of Alan he joins them despite not being invited initially. He also asks for Charlie to pay for drinks on his behalf when trying to charm a woman.
In Season 5's "Our Leather Gear is in the Guest Room," the episode begins with Alan and Jake coming home from clothes shopping, revealing that Alan buys Jake clothes that are far too big for him, saying that he will grow into them (believing that with Jake growing so much, regular clothes are a waste of money). Later in the episode, Alan and Charlie have a fight, resulting in Alan and Jake moving out. When they ask Evelyn if they can move in temporarily, Jake begins to say that Alan was too cheap for a hotel, before being interrupted by Alan.
In Season 8's "Lookin' for Japanese Subs," Jake attempts to produce a volcano effect in his mouth by swallowing a Mentos candy after drinking a can of Diet Coke. Jake's friend, Eldridge, points out that the drink is not the official Coca-Cola brand, with Jake replying, "Yeah, my dad did the shopping."
In Season 9's "Thank You for the Intercourse", when Alan begins behaving like Charlie he tells Jake to take his girlfriend out to dinner as his treat, but only gives Jake one dollar. Later in that episode, Jake tells Walden that Alan is behaving so much like Charlie that the only thing left of him is his cheapness.
In Season 9 episode "A Fishbowl Full of Glass Eyes," Walden gives Alan his wedding ring made of rhodium, and Alan goes to a pawn shop to see how much it's worth. Alan doesn't sell it, even though it was worth at least seven digits as he asks the clerk if his price was the clerks phone number, out of respect for his friendship with Walden. When Walden throws it in the ocean, Alan waits for Walden to go back inside the house before diving into the ocean looking for it.
In Season 9's "Why We Gave Up Women", when it looks like Alan suffered a mild heart attack, he is taken to the hospital. When Walden tells the hospital receptionist that he wants Alan to have the best care possible and that he'll (Walden) cover it, the receptionist tells Walden, "You're gonna have to. This guy has the worst insurance policy I've ever seen. He's got a $500,000 deductible."
One of Alan's worst moments of cheapness happens during the episode "Why We Gave Up Women". As he was having a heart attack, and Walden had dropped one hundred dollars, he crawled to it as he was having the heart attack.
- In "Tucked, Taped And Gorgeous," Alan started to think about being gay himself after meeting a gay man named Greg in his single-parent support group. After meeting the man a couple of times, Alan got congratulated by most of his loved ones for finally "coming out." Alan found himself thinking this could be the reason he's had so many failed female relationships. Alan decides to kiss Greg to check if he is gay. When he tried to kiss Greg, however, Greg told him that Alan was definitely not gay, as he said he knows gay men... and that even if he was, "which you're not" he would state again, he does not find Alan attractive at all but finds Charlie "pretty." Alan jealously told Greg to get out of his car and drove away. Though relieved that he was not gay, Alan mentioned that he felt that "I was letting a lot of people down." 
- In season 7, episode 5 "For The Sake Of The Child", when a drunken Alan and Charlie are reading a relationship help book and get to a section where they must list things they have in common. Alan says that they both fight homosexual panic, but a furious look from Charlie says that only Alan does.
- While packing Alan's belongings in season 8, episode 2, "A Bottle of Wine and a Jackhammer," Charlie sings a modified version of "Happy Days are Here Again" into which he inserts the line, "I'm getting rid of the queer again," although this could be just a simple case of classic name-calling.
- In season 8, episode 12, "Chocolate Diddlers or My Puppy's Dead", Charlie and Alan decide to eat ribs together and watch a movie. Alan says that they do not have to watch a movie because he had recorded Glee, leading Charlie to accuse him of being homosexual.
- In Season 9,episode 6, Walden and Alan kiss (pretending to be gay) and Walden makes a comment "He claims to be straight but his lips opened a little when I kissed him."
- In season 10, episode 1, Walden suggests to Alan that they become gay and get married. Alan is completely on board because Walden is rich but Walden later changes his mind.
- In season 10, episode 12, Walden is in a state of stress and confesses that he cannot get an erection. Alan says he can help, and after some uncomfortable hesitation, says he'll go brush his teeth. Walden then says he was talking about getting some kind of drug to help with the problem.
- In season 11, episode 9, Alan meets a supposed woman named Paula. They have sex. In season 11, episode 10 it's revealed "Paula" was "Paul" for 40 years, and is actually a man. Alan keeps having sex with him, noting "You don't look... 40".
Although he is more conscientious than Charlie regarding sex, Alan does display some sexual deviance. His pregnancy fetish is revealed in the Season 4 episode, "Repeated Blows to his Unformed Head," when Berta's pregnant daughter Naomi (Sara Rue) visits and delivers. In that same episode, he tells Charlie that the best sex he and Judith ever had was while she was pregnant with Jake.
Throughout the series, Alan has a history of masturbating. In season 7 episode 5 "For The Sake of the Child," Alan tells Charlie that he masturbates angrily when he has trouble sleeping. In one episode Charlie says that he caught Alan having sex with the vacuum, but Alan cites it as an "accident." Charlie says that accidents happen once, and he has caught Alan more than once. In season 8 episode 6 "Twanging Your Magic Clanger", Alan was watching porn movies in his bedroom naked when Charlie walked in and was immediately disgusted. Later, Charlie finds Alan watching movies again naked, this time in his living room. Alan finally tells Charlie he has been masturbating because he wanted to use his prescription sexual enhancement pills before they expired (a nod to Alan's reputation for being cheap). The next day, Charlie came home from a date with Michelle, and Alan was in his car listening to Mariachi music while masturbating. Later that night, Alan went to the movie theater and masturbated, which led to an arrest for exposing himself in public, and Charlie for once had the moral high ground when he disgustedly ignored his brother's phone call begging to be bailed out of jail. In "Humiliation is a Visual Medium", when asked by Charlie how he copes with a lack of sex he responds "take up hobbies, work hard and yank it like a monkey in a mango tree." He also uses Viagra, which his son Jake accidentally took in season 3 episode 16: "Ergo, the Booty Call." In episode 14 of season 8, "Lookin' for Japanese Subs," Charlie states that Alan threw his back out trying to pleasure himself. In the opening episode of season 9, in season 8 one morning when Michelle asked Charlie about a noise she heard he answered that it was Alan masturbating and trying to fall asleep, this is also mentioned in the episode "Nice to Meet You, Walden Schmidt," Alan admitted he "masturbated and cried myself to sleep" while Walden was having sex with two women in Charlie's old bedroom. In "Slowly and in a Circular Fashion" when Walden's mother tried to bribe Alan with sex to vote Walden out of presidency of his company, Alan states "That won't work, I masturbated three times before I got here." It is learned in the episode, "Slowly and in a Circular Fashion" that he can perform auto-fellatio.
Poor luck and misfortunes
Another recurring theme for Alan is that he is constantly stricken with terrible luck and extreme misfortunes, mostly caused by himself and/or Charlie's behavior. This is a cause for his neurotic personality. His misfortune usually revolve around women and money. Alan's poor luck was taken to the extreme in "Frodo's Headshots", where he found out Jake had impregnated his girlfriend, had Walden reveal to Herb that Alan is the father of Judith's daughter Millie, learned that Walden had begun dating Alan's ex-girlfriend Lyndsey while he was at a mental health clinic, got hit with an IRS audit, was told by Walden that he had to move out due to the awkwardness of him being around Lyndsey, failed at a suicide attempt, was molested by a male truck driver, turned away in the rain by his own mother, and was shot to death by Herb at the storage facility where Walden and Lyndsey had moved all of his stuff. While the closing scenes revealed that all of those events happened in a dream, Alan decided afterwards that in any realm of his life, happiness wasn't in the cards for him. Eventually in "Why We Gave Up Women", Alan had a heart attack when told by Walden he can't move back in, although a variety of events (ranging from residual sympathy for his plight to Walden's marriage proposal to Zoey being rejected) have allowed him to keep living there anyway as Walden desperately needed a friend.
- "Charlie Sheen Fired From 'Two and a Half Men'". HollywoodReporter.com. 2011-03-07. Retrieved 2013-06-08.
- "Two and a Half Men". Trivia. The Internet Movie Database. Retrieved May 27, 2008.
- Lorre, Chuck; Aronsohn, Lee; Roberts, Mark; Gorodetsky, Eddie (2006-01-23). "Humiliation Is a Visual Medium". Two and a Half Men. Season 3. Episode 13. CBS.
- Lorre, Chuck; Aronsohn, Lee; Gorodetsky, Eddie; Beavers, Susan; Foster, Don (2007-04-09). "Smooth as a Ken Doll". Two and a Half Men. Season 4. Episode 19. CBS.
- Lorre, Chuck; Aronsohn, Lee; Roberts, Mark; Foster, Don (2007-03-18). "It Never Rains in Hooterville". Two and a Half Men. Season 4. Episode 18. CBS.
- Episode 163 (8.2) "A Bottle of Wine and a Jackhammer"
- "A Pudding Filled Cactus"
- "Three Girls and a Guy Named Bud"
- "A Bottle of Wine and a Jackhammer"
- Episode 8.4, "Hookers, Hookers, Hookers"
- Lorre, Chuck; Aronsohn, Lee; Roberts, Mark; Foster, Don (2007-04-23). "Tucked, Taped and Gorgeous". Two and a Half Men. Season 4. Episode 21. CBS.