A man who escorts wealthy widows in New York's Upper East Side takes a young aspiring playwright under his wing.

Van Wilder is a guy who has been at his college for seven years. He spends most of his time throwing parties and "fund raisers". When his father decides that it's time for tough love, he doesn't pay his tuition. So Van becomes a professional party thrower. At the same time, Gwen who writes for the college paper, is tasked with doing a story on him, but Van is too busy partying to do that. So she writes it using info from people who talk about him and writes an unflattering piece, which doesn't make him happy. He then dares her to see if she can get the true story but is more interested in trying to score with her, which is not easy because she has a boyfriend, who is a snob, and who is not too happy with the amount time she is spending with him. So he tries to get rid of him.

Andrew Largeman is a semi-successful television actor who plays a retarded quarterback. His somewhat controlling and psychiatrist father has led Andrew ("Large") to believe that his mother's wheelchair bound life was his fault. Andrew decides to lay off the drugs that his father and his doctor made him believe that he needed, and began to see life for what it is. He began to feel the pain he had longed for, and began to have a genuine relationship with a girl who had some problems of her own.

A successful New York businessman leads a double life as a computer thief.