A Night in the Life of Jimmy Reardon (1988)

A high school graduate receives an ultimatum from his father to improve his life or else study at a business school chosen by his father. However, he chooses a third option - to go to Hawaii. But how will he do that with no money whatsoever? With River Phoenix playing the role of a charming womanizer, this coming-of-age story is one that you should definitely watch!