As far back as his awkward days in junior high school, a black cloud of horrific luck has dampened Jack’s love life. Now, middle-aged and single, he recounts twelve of his most memorably bad dating experiences. Follow along with Jack as he endures one hilarious and short-lived romantic relationship after another. Each chapter represents a different woman in this poor man’s never-ending struggle to maintain some level of dignity and optimism while looking for love. Share is Jack’s humiliation as he learns valuable life lessons such as; never donate your hair to a charity until you have all the facts, breast implants can deflate, and age does make a difference.