Annie Matopoulos is a young, single woman who has taken on an incredible task - serving as a surrogate for her sister. Jealous of the attention that Annie receives while being pregnant, her friend Cassie decides she must have a "story" as well, and decides to masquerade as a virgin to attract a man. Meanwhile, when Carter is fired from his accounting job and comes home early, he finds his fiancé Liz in bed with a unique gift from her bachelorette party. Also, Judd Rouscher and his friend Bowman end up on a cross- country flight with Jennifer Love Hewitt, who is on Judd's "celebrity exemption list," allowing him sleep with her without marital consequences. When Judd ends up actually sitting next to her, he must decide what to do with this opportunity.

Judd and a colleague are in for a surprise when they crash a party; Ricky tries to avoid post-date responsibilities; Annie goes on a date with a man who is overly interested in her pregnancy.