Moving from small-town Iowa to Chicago, an ambitious personal-stylist hires a professional photographer to help promote her new fashion venture; a partnership which teaches her that when it comes to finding love and success in the city, all you need to do is stay true to the style in your own heart.

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.