Donovan Donaly (Geoffrey Rush), a soap opera producer, comes home unexpectedly early to find his wife Bonnie (Stacey Travis) with her ex-boyfriend, a pool cleaner named Ollie (Jack Kyle), even though the Donalys have no pool. Miles Massey (George Clooney), a top divorce attorney and the inventor of the "Massey Pre-nup", a completely foolproof prenuptial agreement, becomes Bonnie's lawyer. He is victorious in the divorce case, leaving Donovan with nothing. Meanwhile, Rex Rexroth (Edward Herrmann) is having a sexual roleplaying session with a blonde in a motel room when a private investigator named Gus Petch (Cedric The Entertainer) bursts in and records everything with a video camera. He takes the video to Rex's wife, Marylin Rexroth (Catherine Zeta-Jones), who married Rex solely to obtain wealth and independence via a divorce. Rex hires Miles. Marylin learns from her friend, a wealthy fellow serial divorcée named Sarah Sorkin (Julia Duffy), that Miles is a dangerous opponent.