Max would do anything for his best friend, Brad. Anything except date a kleptomaniac. His grandparents raised him with a firm set of morals and rules. But Brad's fiancée insists on the double date.

Cassi is freshly moved back to Denver after a bad break-up. She's hesitant about her first date in a year, especially a blind date, but her best friend, Becca, pushes until she agrees.

Half way through a colossal flop of a double date, Max has no interest in seeing Cassi again, and vice versa. But in a twist of fate, Becca and Brad announce they've moved up their wedding to Christmas Eve. Three weeks away. As the best man and the maid of honor, Max and Cassi are stuck together wedding planning. Cassi is funny, kind, and—much as Max doesn't want to admit it—beautiful. Problem is, he can't forget the stories about Cassi's days in college as an unchecked kleptomaniac.

Cassi tries to make the best of the situation. Much as she tries to connect with the handsome man she's forced to work with, nothing she says seems to be right. One minute they're having great conversation and the next he's a complete ass.

Then it hits her. He has to know about her past. The single night that drove her out of the state and still haunts her. With the wedding looming and a lonely Christmas on the horizon, emotions are high. And emotions don't always follow the rules.