In the Yardley College, Gatsby Welles learns that his girlfriend Ashleigh Enright will travel to Manhattan to interview the cult director Roland Pollard for the college paper and he plans a romantic weekend with her. Gatsby is the son of a wealthy family in New York and Ashleigh is from Tucson and her father owns several banks. He has no attraction to study in Yardley but gambling and Ashleigh. When they arrive in Manhattan, Gatsby does not tell his parents that are planning a fancy party in the evening. Ashleigh meets Pollard and he invites her to a screening of his new film with his writer Ted Davidoff. Meanwhile Gatsby stumbles upon his friend, who is cinema student, and he accepts to participate in a kiss scene with Chan Tyrell, who is the younger sister of his former girlfriend. Along the rainy weekend in New York, Gatsby and Ashleigh have new experiences and discoveries.