|Directed by||Michael Ian Black|
|Produced by||Jamie Gordon
|Written by||Michael Ian Black|
|Distributed by||Metro-Goldwyn-Mayer Pictures
|Release date(s)||September 10, 2006|
|Running time||90 minutes|
|Box office||$11,492,406 (Worldwide)|
|This article needs additional citations for verification. (June 2012)|
Against the advice of his best friend Ted (Michael Weston), Anderson (Jason Biggs) publicly proposes to his girlfriend Vanessa (Audra Blaser), while dressed in a cupid costume. The shock of the unexpected proposal leads to her instantaneous death. Utterly devastated and distraught, Anderson quits his job and goes into mourning. A year later, Anderson is still obsessed with his perfect (and dead) former girlfriend. While Ted and Anderson are lunching together in a diner, to help him move on, Ted persuades Anderson to give romance one more try. To placate his friend, Anderson agrees, looks around, and asks attractive waitress Katie (Isla Fisher) to marry him. To both men's utter astonishment, she accepts Anderson's proposal.
Anderson and Katie then decide to take things slow, the same day she moves into Anderson's apartment. Meanwhile Anderson is feeling guilty as when he is accidentally knocked unconscious he talks to his former girlfriend, the late Vanessa, promising to be ever faithful. However he goes ahead with plans to meet Katie's parents, and brings Katie to meet his parents. The pair soon begin to get on well with each other.
Katie's father, Smitty, breaks out of jail to walk her down the aisle. He arrives at his ex-wife (Katie's mother)'s house and through their long lost passion for one another, their love sparks again, much to Stuart's (Lois's current husband) discomfort.
After a falling out over Anderson's late girlfriend, Anderson and Katie's relationship looks to be over. This pivotal moment in the film leads to the pair finally declaring their fondness of one another. The couple suddenly run off to Atlantic City, with help from Ted. Anderson, Katie, Ted and the rest of the party drive to Atlantic City in a car from the car dealership where Ted works (under the pretense of test driving the vehicle). Katie's ex-boyfriend, William, tries to persuade Katie that they should be together. He proceeds to assault Anderson on the way to their wedding. Ted's boss reports the car stolen, and in an unfortunate event, they crash into a police car, resulting in their arrest.
Meanwhile, Katie's parents know where they're headed and make their way there, stopping to rob the Tuxedo Depot in preparation for the wedding. Katie's parents are then arrested for robbing the store. They all end up in the same police station, and Anderson's parents also turn up after he calls them. In a lucky turn of events the group is able to escape from the station after stealing an officer's gun and locking them in a cell. At this point Anderson and Katie establish for the final time that they want to get married, and for the first time the whole group is in favor. Now in a police van, which the policemen let them use, they drive to Atlantic City and Anderson and Katie finally get married. However, as soon as they step outside they are all arrested. Anderson and Katie spend their honeymoon in jail and bribe a judge with a blender they received as a wedding present.
- Jason Biggs as Anderson: He is nervous and uptight. He is a mental wreck after the death of his girlfriend and attempts to return his life to normal by asking a complete stranger to marry him.
- Isla Fisher as Katie: She is a waitress at a local restaurant and has her own relationship problems when her boyfriend proposes to her. Confused and undecided on what to say to her boyfriend William, she is overwhelmed by Anderson's spontaneous proposal, and on a whim she agrees. She sees this as a way of escaping her current relationship and follow in her parents footsteps.
- Michael Weston as Ted: He is Anderson's best friend and works at a car dealership. After pushing Anderson to try at romance again, he helps Anderson and his new friends take a "very long test drive".
- Ebon Moss-Bachrach as Matador: He is Katie's friend and works in the diner. He is obsessed with performing and the circus; throughout the film he attempts daring circus acts, usually causing himself pain. He is of Russian descent, and drives a very cheap Soviet car, the Zaporozhets ZAZ-966 from the 1970s.
- Edward Herrmann and Margo Martindale as Lyle and Betsy: They are Anderson's parents. Anderson's mother was very fond of the late Vanessa, and his father is very supportive of his son. The two are seen to lead a very sexually orientated relationship.
- Joanna Gleason and Matt Malloy as Lois and Stuart: Lois is Katie's birth mother, but after Katie's father, Smitty, went to jail, she married Stuart, a hard working Jewish man who made money by selling Jewish toys.
- Joe Pantoliano as Smitty: He is Katie's real father, who during the film is serving time in jail. On hearing that his daughter is getting married, he proceeds to escape from prison to walk her down the aisle.
The film is set in Staten Island, New York. A lot of the scenes are set in the neighborhood of West New Brighton. The scene outside Gregorio's Florist where Anderson and Katie hug and kiss as well as all the diner scenes are filmed on Forest Avenue, West New Brighton.