Ok, this movie takes place at a college. The main caracter owes money to a bookie so he decides to sell calanders with pictures of male athletes attending the school. He features a pic of his best friend who is a diver. This calendar is seen by a magazine editor who wants to use his friend as "the new look of the 90's". When rumors that the friend got paid for the calendar spread through school, the friend gets school/ scholarship troubble. So the main character plans an elabrate scheme to make the magazine editore change her mind about his friend and use his bookie instead.

Campus Man (1987) (http://www.imdb.com/title/tt0092717/)