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.
Aspiring New York City artist, John Hollar returns to his Middle America hometown on the eve of his mother’s brain surgery. Joined by his girlfriend, eight months pregnant with their first child, John is forced to navigate the crazy world he left behind.