Judy Howard, a recently widowed woman travels in her Winnebago motorhome from California to Illinois accompanied by her cat, Sportster, and a life-sized polyester doll, riding shotgun whom she calls Cowboy Jack. By the invitation of her first love, Brad, she is returning home to attend her 40th high school reunion after fleeing from family and Brad forty years ago to escape the shame and horror of an illegal abortion as the result of being drugged and date raped at the age of sixteen. Always haunted by nightmares of the rape, by dreamy memories of her Brad and by constant regrets, the trip becomes an opportunity to confront her lifelong question of "What if...?" Gathering up her shaky courage, Judy heads home to face her past and who knows? Her future? The odyssey is a deep examination of her feelings and about the woman she has become since she snuggled in the backseat of Brad's 57 Chevy. Brad, who is married only to the police force the past forty years, has lived his life with regrets and guilt, too, always tortured with his own "What ifs?" When he invites Judy to the reunion his mind is made up. He will not waste another moment wondering. He is going to pursue the love of his life and end his doubts. As Judy nears Springfield and Brad comes close to taking down Pit Bull, the biggest drug dealer in the Midwest, they are both confronted with the past when Pit Bull threatens to put an end, not only to the mysteries of the past, but Brad and Judy's future.