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.

When Sheila comes to stay with Kat to avoid being home alone, Sheila's lack of boundaries leads them to try therapy; 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; Kat tries to figure out where her relationship with Max stands.

Kat decides to join the local gym to try to get in shape; Randi and Daniel struggle to take their relationship to the next level; Phil deals with the realization that one of his favorite childhood books is racist.