Chase Storm is a rich, young bachelor with no intention of settling down. His reputation as the town's playboy is ruining his family's name, so his brothers decide to take action. To tame their youngest brother's appetite for women, they offer him a sweet deal. Unwilling at first, Chase finally agrees to take on the challenge and is introduced to Madison Atkins-Morgan.

Madison, a widow, has moved back to her hometown of Tyler, Texas. After losing her husband and twin sons in a car wreck, she needs a fresh start. When things don't go as planned, she finds herself in a slump. Four years later, after having isolated herself, she decides to rejoin the real world and start living again. Unaware of Chase's reputation for being a ladies' man, she accepts his dinner invitation.

They've met before, but he hadn't seemed interested in her during any of those brief encounters. Now, however, there is a definite connection between the bachelor and the widow. When his reputation comes to light, she chooses to continue their budding relationship. She is falling in love with the person the whole town warned her about, and she couldn't be happier--until she discovers she was part of a wager that could cost both of their hearts.