After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.

Famous pop star Ricky Prince has grown tired of the spotlight and the pressures of fame. He makes the acquaintance of Ralph Bitondo, a pizza delivery boy who looks almost exactly like Ricky -- so much so that the two decide to trade identities for a while.

Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet—both blissfully unaware that he's trying to put her out of business.