Jerry Falk (Jason Biggs) and David Dobel (Woody Allen), who meet at a business meeting, become fast friends. Their commonality is that they are both fledgling New York City based comedy writers, largely writing material for stand-ups, are Jewish (although David is an atheist), and are each of bundle of different neuroses. Their big difference is that Jerry is twenty-one, while David is sixty, with forty more years worth of life experience, knowledge, and neuroses. While Jerry writes full time - he is also working on a novel - David has kept his day job as a public school teacher just in case. In their relationship, David becomes somewhat of Jerry's mentor, providing advice on Jerry's life issues, most which revolve around the fact that Jerry is a product of inertia, having trouble leaving anyone. That's why Jerry's still with the only manager he's ever had, Harvey Wexler (Danny DeVito). Jerry not only being Harvey's only client (which is a testament to his effectiveness in the job), Harvey also has a twenty-five percent take as stipulated in their contract, which he wants to extend for another seven years. That's why Jerry is still in therapy with a psychiatrist who has done him no good, and who advised Jerry to stay in therapy with him as opposed to taking a job in Los Angeles, California. But that not being able to leave largely applies to his love life. Jerry already has one divorce. He is having problems with his current girlfriend Amanda (Christina Ricci), who he believes is the love of his life. He fell in love with her at first sight, when he was already in a cohabitational relationship with Brooke (KaDee Strickland), and Amanda dating Jerry's friend, Bob Stiles (Jimmy Fallon). Even after Jerry began sleeping with Amanda, he could not be up front with Brooke about the situation, leaving her to figure out his lies. What Jerry is unable or unwilling to see is that Amanda not only manipulates him, but that he focuses on the things between them that make them truly compatible, while disregarding those many more things which make them incompatible. What has made their relationship more difficult of late is that her mother, who is trying to find herself, has moved in with them in their small apartment. Despite David's unique view of life, he may be able to see Jerry and Amanda's relationship more clearly as an objective bystander. The question becomes how much of David's advice Jerry will take in its entirety.