Natalie Young has everything going for her: she's beautiful, she's smart, she's successful, and she's got a great best friend. There's just one problem: she can't keep a boyfriend because of a medical condition she has. 

Jason Pruitt, a handsome high-school football star, makes a bet with his friends that he can win the affections of Sara Krason, the shrewish, homely, overweight girl no one at school likes. Things go awry when Jason starts to actually fall for Sara, and he must decide whether he wants to continue with the bet and the status quo or admit his feelings for Sara and lose his status.