In the midst of veteran con man Nicky's latest scheme, a woman from his past - now an accomplished femme fatale - shows up and throws his plans for a loop.

Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.

A miserable conman and his partner pose as Santa and his Little Helper to rob department stores on Christmas Eve. But they run into problems when the conman befriends a troubled kid.

Nicky Spurgeon is an extremely accomplished con man who takes an amateur con artist, Jess, under his wing. Nicky and Jess become romantically involved, and with Nicky's profession of being a liar and a cheater for a living, he realizes that deception and love are things that don't go together. They split, only to see each other three years later... And things get messy.