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.
Kat's mom, Sheila, 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 at "The Middle C". Meanwhile, Kat's Cat Café employee Randi confronts a customer, Daniel, who never tips.
Kat wins a free trip to Puerto Rico for herself and a friend, but she doesn't have anyone to go with her. Her friends convince her to go alone, but she makes a last-minute change of plans. Meanwhile, after being left in charge of the café, Randi and Phil have trouble with the new register.
When 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.
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 and Phil deals with the realization that one of his favorite childhood books is racist.
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 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. Meanwhile, Randi tries to figure out the perfect gift for Daniel for their anniversary.
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.
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. Meanwhile, Max offers to help tutor Carter's son, CJ, in English.