Meredith Parks just wants to live. Two years after a fatal car crash takes the life of her brother, Meredith decides she can't spend eternity being sad. So when a well known brown eyed boy proposes a bet fueled by interest, pride, and arrogance, Meredith decides to live on the wild side and agree. Kaleb Matthews was a heart breaker. When a certain brunette catches his eye, he can't help but make the legendary proposal to her, in hopes of yet another heart to claim as his. This having been something he's done for a long time, he see's no problem in making another girl fall. Of course, it's all fun and games until they both realize what they're in for. Five dates, Two people, One love.