Cole King lives the bachelor's dream life. He runs the family construction company and spends his free time in Southern California riding freestyle motocross with his two friends, Denver and Rodeo. Being the son of legendary rock star, Nicky King, Cole has always followed in his dad's footsteps, bouncing from girl to girl and never really stopping to fall in love. But when Rodeo bets Cole that he can't land a date with his neighbor, Kensington Modante, heiress to the Modante Winery, he accepts the challenge. Cole soon discovers that win or lose, it's a bet that will turn his heart upside down.

Kensington "Kensie" Modante has never been able to find the man that can win and keep her heart. She's decided she just doesn't need a man to stir up her contented, albeit slightly dull life where she spends most of her time helping her dad run his winery and riding horses. When Kensie meets Cole King he is just interesting and hot enough to give romance another try. But has she risked her heart for another chance at love or disappointment?