When Alison Scott is promoted in E! Television, she goes to a night-club to celebrate with her older married sister Debbie. Alison meets the pothead reckless Ben Stone and while having a small talk with Ben, Debbie's husband Pete calls her to tell that their daughter has chicken pox. Debbie leaves the place but Allison stays with Ben, drinking and dancing along all night; completely wasted, they end up having a one night stand. Ben does not use a condom and eight weeks later, Allison discovers that she is pregnant. She calls Ben and they decide to try to stay together and have the baby. However, Ben needs to grow up first to raise a family of his own.

Early thirty-something dentist Dr. Charlie Logan has never experienced true love, despite having had a number of girlfriends over the years. After an announcement by one of his ex-girlfriends as such at her wedding, Charlie gets a reputation as being a good luck charm. Every woman he has slept with has met and married her dream man immediately following. He is encouraged to exploit this reputation by his long time best friend, Dr. Stu Klaminsky, a sex obsessed, sex starved schlub who became a plastic surgeon just so that he could masturbate over the sight of women's breasts. Charlie doesn't want to be solely a stepping stone for women, which is how they end up treating him once he gains this reputation as a lucky charm, but rather one's true love. He believes the woman of his dreams is accident-prone Cam Wexler, who works as the penguin caretaker at the aquarium. Cam initially doesn't want to date Charlie because of his reputation as a one-night stand type of guy. Charlie in turn doesn't want to sleep with Cam as he is certain she will find her true love after they do. Cam's true love seems destined to be penguin expert Howard Blaine. To get to true happiness, Charlie feels he needs to speak to Anisha Carpenter, who he feels is the cause of his current problems. Anisha ends up helping him in a way he doesn't expect.

In Manhattan, Ashley Albright is a lucky woman and very successful in the agency where she works. The clumsy Jake Hardin is an unlucky aspirant manager of the rock band McFly, who is unsuccessfully trying to contact the entrepreneur Damon Phillips to promote his band. When Ashley meets Jake in a masquerade party, they kiss each other, swapping her fortune with his bad luck.

Connor Mead, a successful fashion photographer and a Lothario keen on casual sex, goes to his younger brother's wedding to convince him not to marry. He arrives at his dead uncle's estate during the rehearsal the night before the wedding; he starts in, taking his brother aside, trashing marriage. Later in the men's room, his uncle, who taught Connor all he knows about women, appears to him, confesses to have been wrong, and tells Connor that three ghosts will visit him that night: the ghosts of girlfriends past, present, and future. Connor has already set the breakup in motion. Can he learn anything from his life and fix what he's broken?

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