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.
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 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.
Carter hosts a Halloween Octoberfest party at The Middle C, but struggles to get customers in. Meanwhile, Kat continues her journey to find a donor and Phil has a great night with a potential love interest.
Kat and Max finally go on a first date, after a steamy hookup, but they can't seem to act like themselves. Meanwhile, Carter attempts to train his son for track but realizes Randi might make a better coach.
Kat is drained from helping Sheila run errands all over town. Meanwhile, Phil is exhausted from partying every night with his new boyfriend, Jalen, and Carter needs a self-esteem boost.
Kat's Murder Mystery-themed Friendsgiving dinner isn't a crowdpleaser, and Phil has a romantic dilemma. Meanwhile, Kat tries to encourage Max's career ambitions, but she worries that he has a bigger problem.
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.
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.
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 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.
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.
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.
Max hosts singer Zoey Monroe in hopes of advancing his career as a songwriter and although jealous at first, Kat develops a liking to her. Also, after Carter punctures a pipe inside a kitchen cabinet causing a flood in the condo, he and Randi find themselves staying at Sheila's and having a great time together.
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 and Max have some news to share, but attempt to keep it a secret until after Sheila's big birthday bash. Meanwhile, Carter breaks a pre-wedding superstition and thinks he is cursed.
To take her mind off their breakup and Max and Zoey's new successful song, Kat attends a cat show with Sheila and Randi. Kat's competitive side is brought to life, when local cat lover Val thinks Kat and her rescue cat have no chance of bringing home a trophy. Meanwhile, Max's ex, Brigette, attempts to rekindle a romance with him.
Randi and Carter decide to get married at the courthouse, however, things take a turn for the worse when Kat accidentally gets Randi's wedding ring stuck on her finger. Also, country superstar Russell Dickerson offers Max a life-changing career opportunity.
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