Plot

Christina Walters spent years avoiding men, then suddenly met her perfect match while hanging with her best friends, Courtney and Jane. When she finds out that he has left town, she and Courtney set out on a trip.

Christina Walters and Courtney Rockcliffe take their roommate her out on the town to try to ease her relationship-induced depression. During their attempts to find her "Mr. Right Now", Christina meets Peter Donahue. Missing her opportunity with him that night, Christina is talked into pursuing him to his brother's wedding.—Sean Lewis <agvii@yahoo.com>

A group of men are being interviewed regarding Christina Walters (Cameron Diaz) who introduce her as a player and a user of men in the swinging singles market. The men include: A neurotic loser who gets a nosebleed when she fails to call him after promising to do so. A man who saw the movie Swingers and is calling her after three 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. Christina Walters is a 28-year-old 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 (who dumped her 3 days before their 1-year anniversary), by taking her out to a dance club and cancel their plans to stay in for pizza. Christina tells Jane not to make herself too exposed and vulnerable all the time. She advocates looking for "Mr. Right Now", instead of "Mr. Right" and says that if the guy is worthy, the "now" part will simply drop away.

At the club, Jane feels out of place and Christina grabs a man passing by to set Jane up with. The guy walks away saying that he has some friends waiting for him. Jane feels that the guy rejected her, but Christina retorts that the guy was simply a jerk. The guy overhears and returns to confront Christina. This is how Christina meets Peter Donahue (Thomas Jane) who confronts Christina for her methods (to set random men up with her friends) before disappearing for the night. Christina tells Peter that he might actually meet a fun woman if he didn't play it so safe all the time.

Meanwhile Jane finds a date all by herself. While in the bathroom with Courtney, she calls him by name (Peter), 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. He explains that he will be attending a wedding on Saturday, and that he's at the club with his obnoxious, womanizing brother Roger (Jason Bateman) to celebrate. Roger comes by to meet Peter and finds Christina at the bar. Roger reveals that he is getting married that weekend. Peter 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. Jane had borrowed Courtney's dress for the previous night, and she wanted to drop it off to the dry cleaners before she joined the girls for lunch. The girls cannot hold their curiosity and find a huge semen stain on Courtney's dress that Jane borrowed.

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". Meanwhile Peter admits to Roger that he liked Christina, but now he can't do anything about it as she is gone and there is no way to contact her.

Courtney arranges for Christina and herself to travel to Somerset, where Peter's brother's wedding is to take place, and they meet Jane's boyfriend (who is at Christina's apartment having sex with Jane). Jane admits to Christina that her boyfriend is very cute, has a huge penis, but is very stupid.

As a recurring gag, they indicate that he is well endowed, causing misery and enjoyment from Jane. After they leave in Courtney's Saab 9-5, Christina and Courtney go on a series of misadventures. Christina finds an old foil wrapped leftover dinner in the back of Courtney's car. Christina throws it out the window, but it hits the windshield. The girls enter a gas station to clean the car and clean themselves. They encounter an exploding toilet (due to which all their clothes get wet), a glory hole discovery, and a motorcyclist who is led to believe Christina is giving Courtney oral sex (the girls were drying their clothes and were driving in their undergarments). 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, they visit a store to replace their wet and ruined clothing, only to come out in extremely gaudy, indiscreet outfits. Christina begins having second thoughts, but a series of coincidences occasions 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. Christina and Courtney help Jane get out of a sexual situation with her boyfriend where the emergency crew was called in.

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 b***h 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.