Annie Matopoulos (Becki Newton, "Ugly Betty") 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 (Krysten Ritter "Breaking Bad") decides she must have a "story" as well, and decides to masquerade as a virgin to attract a man. Meanwhile, when Carter (Kyle Howard, "My Boys") is fired from his accounting job and comes home early, he finds his fiancée Liz (Lindsay Price, "Eastwick") in bed with a unique gift from her bachelorette party. Also, Judd Rouscher (Greg Grunberg, "Heroes") and his friend Bowman (Craig Robinson, "The Office") end up on a cross- country flight with Jennifer Love Hewitt ("Party of Five"), 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.