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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. Worse, in today's single world, Cal, who hasn't dated in decades, stands out as the epitome of un-smooth. Now spending his free evenings sulking alone at a local bar, the hapless Cal is taken on as wingman and protege to handsome, thirty-something player Jacob Palmer.