When Cal Weaver (Steve Carell) discovers that his wife (Julianne Moore) wants to end their marriage, he reluctantly faces the unwelcome prospect of single life with the counsel of the younger and smoother super-bachelor Jacob Palmer (Ryan Gosling). Meanwhile, Cal's adolescent son, Robbie (Jonah Bobo), has formed an unquenchable crush on his 17-year-old babysitter (Analeigh Tipton) -- but is she more interested in Robbie's recently unwed father?