Plot[ edit ] In an opening scene, a group of men are interviewed regarding Christina Walters Cameron Diaz who introduce her as a player and a user of men in the swinging singles market. A neurotic loser who gets a nose bleed when she fails to call him after promising to do so. A man who saw the movie Swingers and is calling her after 3 days, only to find that she gave him a number for Moviefone. A man whose masculinity comes into question when he attempted to court Christina and was denied claiming her to be a lesbian A very talkative man who ends up propelling himself off an exercise bike when he starts talking about Christina.
The scene shifts back to the sexist man whose claims of Christina's lesbianism causes an entire crowd of women to attack him with baseball bats and the movie moves along, introducing Christina Walters, a successful interior designer and Courtney Rockcliffe Christina Applegate who is a divorce lawyer as they console their friend and roommate Jane Selma Blair , who had recently broken up with her boyfriend Kevin, by taking her out to a dance club and cancel their plans to stay in for pizza.
At the club, Jane feels out of place and Christina grabs a man passing by to set Jane up with. She meets Peter Donahue Thomas Jane who confronts Christina for her methods before disappearing for the night. While in the bathroom with Courtney, she calls him by name, leading her to suspect that he got under Christina's skin and she is actually attracted to him which she denies.
After running into Peter again, Christina buys him a drink and they spend time together, Peter explaining that he will be attending a wedding on Saturday and he is at the club with his obnoxious, womanizing brother Roger Jason Bateman to celebrate.
He invites Christina and Courtney to an after-party at their hotel, but Christina goes home and later regrets not going. The next day, Christina cannot stop talking about Peter while Jane deals with an embarrassing "cleanup" from her fun with the guy she met the night before. In the unedited version, Jane returns to the lunch and the women talk about always complimenting men for the sizes of their penises , eventually breaking out into a restaurant-wide "Penis Song". Courtney arranges for her and Christina to travel to Somerset where Peter's brother's wedding is to take place and they meet Jane's boyfriend as a recurring gag they indicate he is well endowed causing misery and enjoyment from Jane.
After they leave, Christina and Courtney go on a series of misadventures including an exploding toilet, a glory hole discovery, and a motorcyclist who is led to believe Christina is giving Courtney oral sex. Meanwhile, Jane encounters her boyfriend at her retail job and is nearly caught having sex with him in the changing rooms.
When Christina and Courtney finally get to Somerset, Christina begins having second thoughts after visiting a store to replace their wet and ruined clothing only to come out in extremely gaudy, indiscreet outfits, but a series of coincidences gives her a change of heart and they go to Peter's brother's wedding.
Arriving, they discover that it is Peter, not Roger who is getting married and the pair nearly ruin the ceremonies in their attempts to escape. Peter and his fiance then decide that they do not want to marry each other and they call off the wedding much to her father's chagrin while Christina returns home and back to a newly unfulfilled life of being single again.
Later, Peter finds Christina's address in the log at the store they bought their clothing in and tracks her down. Christina, determined not to fear the commitment, kisses Peter and then walks away disappointed. Sometime later, Courtney is dating a doctor and is clearly very attracted to him, and Peter is interviewed like the men at the beginning of the film, retelling his version of the events calling her a bitch and a player, but ultimately revealing that he and Christina are together, having gotten married and are living very happily with Jane and Courtney and Roger as well.
Whether they all live together is left ambiguous.