It's 1953 and single mom Ann Reynolds can't seem to get into the perky spirit of the decade, so after dropping her sons off at summer camp, she sets out on a journey to discover what's left of her life. Her best friend Charlie isn't going along for the ride. He's not exactly husband material, and it's become obvious that Ann needs more from him than he can ever give. When a stranger name Trey joins Ann on her trip, Charlie feels honor bound to make sure the guy isn't out for one thing. After all, she deserves better. But if all Ann is looking for is a summer fling...well, hell, Charlie isn't opposed to helping her out one last time. And he's got no problem if her new friend wants to come along for the ride.