Fortysomething Cal Weaver (Steve Carell) thinks his marriage is perfect, until his wife Emily (Julianne Moore) asks for a divorce. Now Cal is single and looking for love with the help of expert ladykiller Jacob Palmer (Ryan Gosling), who gives Cal's manhood a remarkable makeover. Amid inappropriate crushes and romantic encounters, Cal and Jacob discover that being a player without the right partner isn't just crazy and stupid, it's impossible!