As their marriage unravels, Alex faces middle age and divorce, seeking new purpose in the New York comedy scene. Meanwhile, his wife Tess confronts sacrifices made for their family, forcing them to navigate co-parenting and identities.

Since she was a little girl, it's been drilled into Amy's head by her rascal of a dad that monogamy isn't realistic. Now a magazine writer, Amy lives by that credo - enjoying what she feels is an uninhibited life free from stifling, boring romantic commitment - but in actuality, she's kind of in a rut. When she finds herself starting to fall for the subject of the new article she's writing, a charming and successful sports doctor named Aaron Conners, Amy starts to wonder if other grown-ups, including this guy who really seems to like her, might be on to something.

When seasoned comedian George Simmons learns of his terminal, inoperable health condition, his desire to form a genuine friendship causes him to take a relatively green performer under his wing as his opening act.