At fortysomething, straight-laced Cal Weaver (Steve Carell) 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 (Julianne Moore), has cheated on him and wants a divorce, his "perfect" life quickly unravels.

In today's single world, Cal, who hasn't dated in decades, stands out as the epitome of un-smooth. Spending his free evenings sulking alone at a local bar, the hapless Cal is taken on as wingman and protégé to handsome lothario Jacob Palmer (Ryan Gosling). In an effort to help Cal get over his wife and start living his life, 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.