At forty-something, straight-laced Cal Weaver is living the dream-good job, nice house, great kids and marriage to his high school sweetheart. But when Cal learns that his wife, Emily, has cheated on him and wants a divorce, his "perfect" life quickly unravels. Cal is taken on as wingman and protégé to handsome, thirty-something player Jacob Palmer. Jacob opens Cal's eyes to the many options before him: flirty women, manly drinks and a sense of style that can't be found at Supercuts or The Gap. Cal's son is crazy about his 17-year-old babysitter, who harbors a crush on Cal. And despite Cal's makeover and his many new conquests, the one thing that can't be made over is his heart, which seems to keep leading him back to where he began.