Hillary Wilkes is the unlikely middle-aged heroine in this romantic comedy about a woman whose life is a precarious climb on an uphill battle. Toronto, early 2000's. Hillary "Lary" Wilkes is an emotionally and physically challenged, Over Fifty, once a very vibrant woman. She's at the lowest point of her life, having lost her dream job to a younger woman, her self-esteem, and even her sense of humor. Hillary is overweight, underloved and, as a result, feels unlovable - except perhaps from her family, whose encouragement keeps her from bottoming out. But enough of the self-pity: this is the year she will find herself an exciting new career, lose the 20 pounds for good and find the perfect mate. Quit smoking. Sort out her finances and ... well, maybe she can't do it all at once. But with the help of her best friend Becks, her wonderful neighbor Howard, her lovely niece Pumpkin and her loyal brother Roger, and the cheery encouragement from a new friend Dudley, she knows she can do it. One step at a time. With a hitch here and there and plenty of fun and hilarity, Lary reaches for the hilltop. But can she find the perfect job, and the perfect man?