Jerry Falk (Jason Biggs), a fledgling comedy writer with an inept agent, is about to celebrate an anniversary with his girlfriend Amanda (Christina Ricci). There's trouble in paradise: she's late (and has already eaten), she's been uninterested in sex for a few months, and her quixotic mother is moving in with them.
Jerry looks back to meeting Amanda and dumping Brooke (KaDee Strickland). A constant is his friendship with another wannabe comedy writer, a sixty-year-old teacher named David Dobel (Woody Allen), prone to long walks and advice filled talks.
As Amanda's and Jerry's relationship flounders and her mom's noisy presence makes writing difficult for him, he and David plan something different. Wouldn't anything else be better?