Rick Stevens (Wolff) is willing to do whatever it takes to try and win the heart of Nina Pennington (Gomez). Even if this means making a bet with a mobster’s son! The pressure is on, but the mob isn't the only thing that's standing in his way. He'll also have to deal with a group of strippers, his best friend's horny mother, his drug abusing boss, a perverted principal, a priest with a really big secret, if he ever hopes to land the girl of his dreams. No one ever said love was easy.