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.

Nate freaks out when Lydia decides to sell his childhood home so he enlists his father Harrison and friends to sabotage the open house. Jimmy becomes scared about his future with Lydia after a talk with Nate.

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.

Nate, a budding restaurateur, returns from a trip and learns that his best friend has started dating his recently separated mother, Lydia; Nate's previously disinterested father becomes determined to win Lydia back.

Lydia and Jimmy plan a date in public to rebuff Nate's contention that they're not serious about their relationship. Nate, meanwhile, goes on a date with an older woman he meets at a restaurant; and Atticus prepares for a perfect evening with Sam.

Lydia thinks that she may be pregnant and pleads with Nate not to tell Jimmy until she knows for sure. Harrison, meanwhile, makes it clear to Jimmy that he's out to win back Lydia; and Emma writes a country song about Nate's complicated life.

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.

Nate is over anxious that a food blogger is coming to review his restaurant. Lydia is afraid Jimmy is missing doing youthful activities and concocts some drug filled gummies that Nate accidentally eats. Everyone pitches in to get Nate through his special evening.

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.