Cal Weaver (Steve Carell), married to his high school sweetheart, Emily (Julianne Moore), believes his life is perfect. He likes his job, he owns a house and has great kids. All that changes when he finds out Emily is having an affair and wants a divorce.
Cal, who hasn't dated in years, doesn't know what to do. One night as he's drowning his sorrows at a local bar, he meets a handsome, thirty-something Jacob (Ryan Gosling), who opens Cal's eyes to the many options before him.
Meanwhile, his 13-year-old son, Robbie, is crazy about his 17-year-old babysitter, Jessica, who has a crush on Cal. And even when Cal gets comfortable with his new lifestyle, meeting new women and sporting new styles, he realizes he misses his old way of life with his wife and family.