Budding Portland restaurateur Nate's world is turned upside down when he comes back from a business trip to find his lothario best friend and roommate, Jimmy, is now dating his recently separated mother, Lydia. To make matters worse, Nate's previously disinterested dad, Harrison, is now determined to win Lydia back and isn't afraid to use Nate to get what he wants. Stuck between his family feud and his best friend's first serious relationship, Nate's "new normal" forever changes his relationships with his parents, and severely handicaps his own dating life.

When Lydia suspects that she could be pregnant, she begs Nate to keep it a secret from Jimmy until she can find out for sure. As Nate makes every attempt to avoid Jimmy at all costs, Jimmy begins to suspect that his best friend is hiding something and makes it his mission to find out what. Meanwhile, Harrison makes his intentions to win Lydia back clear to Jimmy, setting off some not-so-friendly competition. Elsewhere, Nate's complicated life gives Emma everything she needs to write the perfect country song.