Donald Cerlino only cares about three things: money, getting girls, and gambling. His friends are so impressed with his abilities with women, they start calling him Don Juan. When senior year starts, he's got a list of girls he wants to add to the growing number of notches on his headboard. So when his best friend, Thomas, bets Donald that his skills aren't enough to nab the school valedictorian, Alaina Pizzo, Donald is up for the challenge. What Thomas doesn't know is that Donald has had a crush on Alaina since kindergarten. Problem is, Alaina hates his guts.
When Donald's feelings for Alaina start to show, Thomas begins to turn against him. Thomas wanted Donald to see the error of his ways when it comes to women, not abandon their friendship for yet another girl. The deeper Donald gets, the more he wants a future with Alaina, but that means revealing why he started talking to her in the first place. When Thomas starts threatening to tell Alaina the truth, Donald has to decide if he wants to lose the love of his life or his best friend.
Donald realizes he took a bet he can't win. The great Don Juan may lose everything.