At Yardley College, Gatsby Welles learns that his girlfriend, Ashleigh Enright, will travel to Manhattan to interview movie director Roland Pollard for the college paper, and he plans a romantic weekend with her. Gatsby is the son of a wealthy New York family, and Ashleigh's father owns several banks in Tucson. Gatsby is not enthused about college, except for gambling and Ashleigh. When they arrive in Manhattan, Gatsby does not tell his parents, as they are throwing a fancy party that he is loath to attend. Ashleigh meets Pollard, and he invites her to a screening of his new film with his screenwriter, Ted Davidoff. Meanwhile Gatsby stumbles upon a high-school friend who's shooting a movie, and agrees to participate in a kiss scene with Chan Tyrell, the younger sister of his high-school girlfriend. Throughout the rainy New York weekend, Gatsby and Ashleigh have new experiences and discoveries.