Dr. Jason Bull is the brilliant, brash, and charming founder of a hugely successful trial consulting firm.

Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates."

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.

Lissa, a twenty-year-old girl trapped in rural Pennsylvania, grapples with sex, drugs, love and loss. When a possible pregnancy forces her to take a hard look at her life, both her and the structure of the film mature, illuminating a brighter path ahead.