Kat's former crush and good friend returns to town.
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 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.
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.
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; Randi tries to figure out the perfect anniversary gift for Daniel.
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.
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.
Kat asks Max to help her learn how to salsa dance to impress Oscar; Phil bakes a bun that looks exactly like a celebrity.