Caleb Pierce

Eileen decides it's time to get back to work and applies for a job for the first time since having children. Pat doubts that he's ready to be single. Jimmy explores the world of online dating to help Kenny.

Kenny secures the role of Romeo in the school play, and Eileen offers to help when she learns that Mimi will be playing Juliet.

Kenny throws his own party to celebrate Halloween when Eileen allows him to have it at home, while Jimmy and Shannon put together the ultimate Halloween prank.

With the school prom approaching, Kenny begins to think about potential prom dates, before he and Jimmy brainstorm ways to ask their classmates to prom.