Neurotic Jewish writer Jerry Falk (Jason Biggs) is in love with beautiful aspiring actress Amanda (Christina Ricci), who has several troubling flaws: she hasn't had sex with him in six months, her mother's just moved into their tiny apartment, and she has a pretty nasty eating disorder to boot. It's no wonder, Jerry's problems being what they are and this being a Woody Allen film, that Jerry's in therapy. Unfortunately, it doesn't seem to be working, but when Jerry meets fellow writer David Dobel (Allen) he finds in the older man a mentor and confidant. Trouble is, the advice-spewing Dobel is even more neurotic (actually, paranoid might be the more apt term) and troubled than Jerry.