When Lydia's mother visits unexpectedly, she tries to hide her relationship with Jimmy by implying he and Nate are boyfriends. Lydia also indicates she is getting back together with Harrison to further complicate things.

Concerned about Nate's uptight nature, Jimmy and Lydia sign him up on a dating site. After a succession of awful meet ups, Nate connects with Annie. Jimmy then recalls that he has seen Annie before due to her infamous Internet activities.

Lydia asks Nate give Jimmy a busy night off but his replacement as bartender Timmy works out so well, Jimmy feels threatened. As Nate and Timmy start hanging out, Jimmy decides to compete to get his friend back.

Jimmy falls into a deep depression after his breakup with Lydia and Nate feels responsible. Sam and Atticus help Nate show Jimmy his future if he can't make decisions while Harrison agrees to divorce Lydia.