The day before the wedding of Elise and Michael in Los Angeles, their friends from college gather to attend the bachelor and bachelorette parties and then the ceremony the following day. Rich and Samantha are the best man and maid of honor, and themselves a couple, although Rich is wary at the idea of marriage, while Samantha is pushing him to consider it, while hiding her pregnancy from him. Sam Malone, nicknamed "Pockets" because he can always find the right item in his pockets, is flying in from Thailand, still harboring an unrequited love for neurotic Lana since their college days, when she broke his heart. The group also includes Quentin, a spirited film agent, and Simon Black, a self-important movie star who shows up in the company of Franklin Brauner, director of his next project, described as "a metaphysical western, sort of El Topo meets The Matrix". Jennifer, who comes from London, was Elise's one-time girlfriend in college, is still in love with her and tries to prevent her from marrying Michael. During the day, Michael's estranged father Jonathan also shows up, hoping in a reconciliation, but is rebuffed. That night, men and women separate to go to their respective parties. The guys go to Vegas on Simon's private jet, while the girls stay at Elise and Michael's home. Once they've reunited, Quentin stumbles onto Elise's sister Sarah, who came earlier as a surprise, and has sex with her not knowing she's just 17-year-old. Pockets confronts Lana about his hurt feelings, then has a fight with Simon, who's particularly condescending toward him, and ends up in jail after soliciting an undercover cop. Jennifer, who's been brusque with everyone, bonds with Lana, and the two of them find themselves having sex, to Lana's surprise. Michael explains to Rich that marriage is not the "next step to the grave" he thinks it is, then reveals to Elise the truth about his ex-alcoholic father, whom Michael blames for his mother's accidental death in a car crash, while a younger Michael was driving. Elise confesses she's the one who invited him to the wedding, not knowing about their troubled past. The next morning, Michael goes to his father's motel, reconciles with him and allows him to attend the wedding. Lana agrees to try and be with Jennifer, exploring an entirely new avenue in her life, much to the chagrin of Donovan, a weird children's entertainer who self-elected as Lana's last minute date for the wedding. Quentin is shocked to find out Sarah's underage, but they arrange to wait for her to be 18 before going public. And Rich proposes to Samantha, who finally reveals her pregnancy.
Cast
In alphabetical order:
Jon Abrahams as Pockets, the out of town friend, in love with Lana
Amy Adams as Elise, the bride
Roger Avary as Franklin Brauner, Simon's next film's director
