Jerry Falk (Biggs) is an aspiring writer living in New York City. He falls in love with Amanda (Ricci) and leaves his girlfriend Brooke (Strickland) for her. Jerry then turns to an aging, struggling artist David Dobel (Allen) who acts as his oracle, which includes trying to help sort out Jerry's romantic life.
This film contains examples of:
- Crazy Survivalist: David, besides advising Jerry on comedy and sex, also tells him to have guns in the house, in case something happens and he has to defend his integrity, but the scenarios he puts become more outlandish every time.
- Hot-Blooded: Harvey Wexler, Jerry's agent, is quite hot-tempered, which is only exacerbated by him not seeming to be that great at his job.
- Manic Pixie Dream Girl: Subverted. Jerry falls hopelessly in love with Amanda, but she proves to be an uncompromising, unsure, difficult, and insecure girlfriend.
- Writer's Block: Jerry struggles with writer's block on top of his romantic problems.
- Your Cheating Heart: Jerry already had a girlfriend, Brooke, when he fell in love and began an affair with Amanda.