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. The hapless Cal is taken on as wingman and protégé to handsome, thirtysomething player 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. But 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.