Kat, a woman who struggles every day against society and her mother to prove that she can live a happy and fulfilling life, despite still being single at 39. Which is why she recently spent her entire savings to open a cat café in Louisville, KY. Although Kat celebrates her independence, her single-forever plans may begin to veer off-course, when her former crush and good friend, Max, returns to town.
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 and Phil deals with the realization that one of his favorite childhood books is racist.
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. Meanwhile, Sheila asks Max to help her move some of her furniture to make room for her boyfriend, and Randi asks Phil for help with her photography project.
Louisville has some special visitors — WELCOME TO FLATCH's Kelly and Shrub Mallet stop by, and the one-and-only Robin Thicke is in town for a fundraiser, which Max exploits for his own music career’s benefit. Meanwhile, Kat tries to cut costs at the café in order to pay the rent that her new landlord is demanding.
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 and Kat tries to figure out why. Meanwhile, Phil urges the group to try his mama's moonshine despite their skepticism, and Max finally sells a song to be used in a national commercial, but it ends up becoming a big joke online.
Carter hosts a Halloween Octoberfest party at "The Middle C," but is struggling to get customers in, Randi suggests a ladies night instead, which turns out to be a hit. Meanwhile, Kat continues her journey to find a donor and her next opportunity is closer than she might expect. Phil has a great night with a potential love interest.
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. Meanwhile, Carter punctures a pipe inside a kitchen cabinet causing a flood in the condo. Randi and Carter find themselves staying at Sheila's for the time being.
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. During another hectic day of condo renovations, Randi discovers a secret hideaway, that she hides from Carter and transforms into a place for her to unwind.
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. Meanwhile, Country superstar Russell Dickerson offers Max a life-changing career opportunity and Max must make a big decision about his future.