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Fortysomething straight-laced Cal Weaver is living the dream—good job, nice house, great kids and marriage to his high school sweetheart, Emily. So when Cal learns that his wife has cheated on him and wants a divorce, his “perfect” life quickly unravels. Cal, who hasn't dated in decades, stands out as the epitome of un-smooth so handsome player Jacob Palmer takes him on as wingman and protégé, opening Cal’s eyes to the many options before him: flirty women, manly drinks and a sense of style. 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 Cal back to where he began.