Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.

John and his buddy Jeremy are emotional criminals who know how to use a woman's hopes and dreams for their own carnal gain. Their modus operandi: crashing weddings. Normally, they meet guests who want to toast the romantic day with a random hook-up. But when John meets Claire, he discovers what true love – and heartache – feels like.