For all of his life, billionaire Blake Harrison has firmly believed the route to happiness was keeping his heart free. But after seeing two of his best friends fall hard for women, he's starting to second guess himself. The problem is, if he can't get past the second date with a woman, how can he possibly consider settling down? Jokingly, his buddies bet him he can't go out with the same woman five times. When he gets beaned in the head with a baseball at his team's practice field, trainer Michelle Stewart is the one to patch him up. His buddies immediately set their sights on the beautiful trainer. She's the one, they agree. And after a few dates, Blake begins to wonder if she really is…

Sure, Michelle is attracted to Blake. He's sweet and charming and the hottest guy she's ever dated. But if she's attracted to him, it's got to mean he's wrong for her. For one thing, she works for him. For another, she has a rotten track record when it comes to men, and it's better if she just steers clear of charming, hot guys. Besides, she has to think about her daughter Mollie and what's best for her, too. Even though her mind is telling her no, her heart is shouting that Blake is a big yes. The problem is, listening to her heart has always gotten Michelle into trouble. Could it be possible that her heart is finally telling her the truth? Or is Blake just too big a risk?