40-year-old Andy Stitzer has a cushy job stamping invoices at an electronics superstore, a nice apartment that includes a collection of action figures and comic books, good friends, a nice attitude. But at 40, Andy is still a virgin. His friends think he's a bit of an oddball, but they consider it their duty to help Andy out of his dire situation and decide to go to great lengths to help him. But nothing proves effective enough to lure their friend...

Will Hayes is a 30-something Manhattan dad who is in the midst of a divorce. His 10 year old daughter, Maya, starts to question him about his life before marriage. Maya wants to know absolutely everything about how her parents met and fell in love. Will's story begins years earlier when, as a young, starry-eyed aspiring politician, he moves to New York in order to work on the Clinton campaign. Will attempts a "PG" version of his romantic relationships...