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 fiancée 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.
Annie's friend Jodie scares a guy off by baking for him; a couple learn to embrace their gay son's relationship; a guy takes up knitting to spend time with a woman.
Judd and a colleague are in for a surprise when they crash a party; Ricky (Donald Faison) tries to avoid post-date responsibilities; Annie goes on a date with a man who is overly interested in her pregnancy.
Judd and Colleen indulge in treats from the medical marijuana store and almost miss a family event; a teenager's family tries to give him advice about the prom; an astronaut suspects his girlfriend is cheating.
A man (Beau Bridges) tries to console his son after a breakup; Colleen and Judd think they have found the perfect house; Julia Clark (Emily Rutherfurd) must choose between romance and her career.
Bridget is embarrassed when her boyfriend discovers one of her secrets; Judd's niece turns to him for advice.
Colleen's heart-broken nephew receives an unexpected lesson in love; a flirty receptionist distracts Annie's brother-in-law
Newly shacked-up couple Jodie and Charlie realize they have bedbugs; Judd gives his neighbor the Heimlich maneuver; a guy who helped Annie out of a date once considers leaving his girlfriend for a chance with her.
