Kat's former crush and good friend returns to town.

In celebration of Max's birthday, Kat, Randi and Carter jointly gift him an RV rental so they can roadtrip to the Smoky Mountains together. Gideon decides to join in on the trip, while Randi and Carter bicker over where they should live together.

Kat hires a new baker, Gideon at the Kat Cafe and shows him around town. Meanwhile, Max and Carter wingman for Sheila.

Kat wins a free trip to Puerto Rico for herself and a friend, but she doesn't have anyone to go with her. After being left in charge of the cafe, Randi and Phil have trouble with the new register.

Kat's mom sets her daughter up on a blind date, but it happens to be the same night that Max asks her to be his karaoke partner. Kat's employee Randi confronts a customer who never tips.

Kat and Max move in together and host a Super Bowl party in their new apartment but face some relationship trouble along the way. Meanwhile, Randi tries to make some extra cash.

Kat asks Max to help her learn how to salsa dance to impress Oscar; Phil bakes a bun that looks exactly like a celebrity.

Sheila comes to stay with Kat to avoid being home alone. Sheila's lack of boundaries lead them to try therapy. Meanwhile, Phil and Randi make a road trip to buy Phil's mother medicinal marijuana.

After a visit to the gynecologist takes an unexpected turn, Kat must consider freezing her eggs if she ever wants to have children. Meanwhile, Max and Carter help Phil with his online dating to prevent him from getting catfished, but it turns out Phil may be the one catfishing.

When Carter helps Kat get elected to the local business council, a rift forms in their friendship when she doesn't vote in his favor to keep the bar open later; Sheila asks Max to help her move some of her furniture to make room for her boyfriend.

In the heat of the moment, Zoey kisses Kat at karaoke night. Zoey hopes this moment can be kept between the two of them, but Kat struggles to keep the kiss a secret from Max. Meanwhile, Randi discovers a secret hideaway, that she hides from Carter and transforms into a place for her to unwind.

Kat rents her apartment to Kelly and Shrub from Flatch, Ohio; Max plans to play one of his original songs for Robin Thicke at a local fundraiser.

After taking some time to travel and decompress, Kat is on her way back to Louisville when she is upgraded to first class and seated next to “Jeopardy!’s” winningest contestant, Ken Jennings, on her flight home. Upon arrival, she discovers some significant changes have been made to the cafe by Randi and Phil and Randi’s passion for her job is now straining her relationship with Carter. Max has returned home from his time in Nashville pursuing his music career, with cowboy boots and a big ego to go along with them.

Kat decides that she would like to pursue motherhood and her friends jump at the chance to help her find a donor. Meanwhile, Carter and Max decide to check out a new bar.

When Kat becomes jealous after hearing a song Max wrote, she tries to plan a romantic evening for the two of them to spice up their relationship. Meanwhile, Randi learns how to be a cool yet responsible stepmom.

A customer asks the café to bake his wedding cake, but it’s a tricky situation for Phil. Meanwhile, Kat tries to figure out where her relationship with Max stands.

When Kat gets selected as a finalist for the Louisville Courier Journal's 'Twenty under Forty' list, she decides to join the local gym to try to get in shape. Meanwhile, Randi and Daniel struggle to take their relationship to the next level.

When Randi's cousin comes to town, Kat and Phil convince Randi to let them come out with her to prove they aren't old. Meanwhile, Randi struggles to figure out why Daniel doesn't get jealous.

Kat deals with nerves over her first date with Oscar; Randi tries to figure out the perfect anniversary gift for Daniel.

With Daniel out of town on the day of Randi's big move to his place, Kat offers to help her and discovers an unexpected secret about Daniel's past; Max offers to help tutor Carter's son in English.

Sheila grows jealous after Kat hits it off with her new retirement home friends. Meanwhile, Randi tries to find a way to tell Carter that she doesn't like her engagement ring.

Sheila must supplement her savings after moving to Valley Hills, which has turned out to be quite an expensive senior community. Meanwhile, Randi and Carter think about the future of their family.

Kat pushes Max to enter a jingle contest being held at the Middle C to boost his confidence. Meanwhile, Carter doesn't know how to react when Randi puts nail polish on his son.

It's time for Sheila to renew her driver's license, but she refuses to go take the test; Phil urges the group to try his mama's moonshine despite their skepticism; Max finally sells a song to be used in a national commercial.

Kat joins Max at his rock climbing gym to keep a close eye on him. Meanwhile, Carter has to spice up the bar after being excluded from a Christmas pub crawl.