- Season 1
Knowing that Jimmy needs a little tough love in order to realize a mistake he's just made, Nate enlists Sam and Atticus' help to drive home his point. Elsewhere, Lydia finds herself at a crossroads and takes advice from her boss Parker, while Harrison comes to a realization about his marriage to.
Ready to move forward with her life, Lydia decides to sell the house she once shared with Harrison and enlists the help of realtor Bob Babcock After learning that his mother plans to sell his childhood home, Nate turns to Sam and Atticus to help crash the open house, while Harrison joins in on the plan in his own attempt to win Lydia back. Meanwhile, a frank conversation with Nate causes Jimmy to have doubts about taking things to the next level with.
After Lydia forces him to give Jimmy the night off, Nate hires a temporary bartender named Timmy, who shares an uncanny resemblance to Jimmy. Impressed with his skills and new money-making potential, Nate hires Timmy for the remainder of the week. Not happy with Timmy moving in on his territory, and in on his friendship with Nate, Jimmy suggests a bartending duel to determine who is the best man for the job - and who is the best friend for.
After being told by Lydia and Jimmy that he needs to loosen up, Nate reluctantly agrees to go on a series of dates with women they meet on a dating website. Quickly realizing that speed dating isn't for him, Nate throws in the towel, but Lydia urges him to go on one more date with a girl named Annie. Elsewhere, Sam struggles to write the lyrics to her next song after Atticus points out all of her songs are about Nate. Finally, when Jimmy makes a surprising discovery about Annie, he and Lydia disagree on how to break the news to a smitten Nate.
Just when things are beginning to go smoothly with Jimmy, Lydia gets a major surprise when her uptight mother, Gammy shows up unannounced. Knowing that Gammy would never approve of her new relationship with Jimmy, Lydia is forced to create an elaborate cover-up, which finds Nate drawing the short end of the stick. Meanwhile, Jimmy wants the chance to prove himself to Gammy, but ends up in an awkward position when an innocent mix-up sends their plan spiraling out of control. Finally, Gammy surprises everyone when she reveals her own little secret.
As Nate meticulously prepares for an interview with a major food blogger, Jimmy and Lydia consider taking pot gummy bears to spice up their dating life. However, when Nate unknowingly eats the gummy bears before his interview, Lydia, Jimmy, Harrison and Sam are forced to create an elaborate plan to cover for him.
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.
After Nate suggests they may not be taking their relationship seriously, Lydia and Jimmy decide to prove him wrong by going on a date - in public. Meanwhile, Jimmy calls Nate out for his own lackluster dating style, prompting him to go on a date with a notorious cougar he meets at the restaurant. Elsewhere, Atticus prepares for his own perfect evening enjoying the equinox with Sam. Finally, things take an uncomfortable turn when Lydia and Jimmy run into Nate on his date with Pepper Spinner, who happens to be Lydia's former archrival.
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.
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