Dean Logan is a young rising star of the Chicago financial world. Behind that success is his loyal secretary, Jody. He’s severe and serious at work, but in his private life Dean goes through a series of short-term flings, leaving Jody to clean up after him. Believing that Dean only thinks of her as a sort of custodian, Jody had given up ever having any other kind of relationship with him...but fate has other plans. One day Dean is dumped by the woman he thought was his true love, and he ends up inviting Jody to accompany him to Hawaii instead!