Dr. Cheapskate (2016)

Fresh off of a divorce, thrifty Dr. Kelly has become even stingier. His isolated life is shaken up when he runs into Beau, an old classmate from high school who makes it his mission to help Dr. Kelly get back into the dating game. Against his better judgment, Dr. Kelly listens to Beau's odd pickup tips, putting him in uncomfortable and unusual situations. Making it worse, Beau's other friend Hunter, a guy who gets girls' numbers by smiling, throws down a bet involving women that Dr. Kelly has no chance of winning. Dr. Kelly agrees to the wager and goes all-in to take down the lothario Hunter. Beau pushes Dr. Kelly out of his comfort zone, forcing him to open up his wallet, and testing the limits of their friendship.