Jerry Falk (JASON BIGGS) is a comedy writer whose neurotic and manipulative live-in girlfriend, Amanda (CHRISTINA RICCI), won't sleep with him anymore. Jerry's new friend, paranoid school teacher-cum-comedy writer David Dobel (WOODY ALLEN) doesn't think that's good. While giving him all sorts of philosophical and comedy based advice about that as well as him needing a survival kit and gun, he also tells Jerry that he should dump his washed up manager, Harvey (DANNY DEVITO).
Jerry, who has a weakness when it comes to breaking off unsuccessful relationships - be they romantic or professional - can't bring himself to do that, especially since he's Harvey's only client. He also can't break up with Amanda, despite believing she's cheating on him. Things only get worse when Amanda's alcoholic and washed up singer mom, Paula (STOCKARD CHANNING), moves in with them.
With David filling Jerry's head with all sorts of disturbing thoughts, the young writer must decide what to do in his professional and personal lives.