Kate tries to play matchmaker to Diane and another parent on Warrenâ€™s field trip, but is shocked by what she learns in doing so. Meanwhile, Jackie takes it upon herself to care for Pete when heâ€™s sick â€“ but she finds herself more interested in having the run of the house. Also, Hillaryâ€™s educational skits and songs upstage Bert in his own classroom.
When Jackieâ€™s homemade costume nearly ruins Bertâ€™s Halloween, Kate steps in with the costume he wanted, and Bertâ€™s so overjoyed that he asks Kate to take him trick-or-treating. This leads to a fallout between Jackie and Kate, which gets worse when Bert goes missing. Meanwhile, Pete tries to get a neighborhood teen to admit he egged Peteâ€™s house last Halloween.
Finding it more and more difficult to spend time alone and away from Dianeâ€™s constant demands, Kate and Pete sneak away for a romantic tryst at the school fundraiser. But when they get trapped, truths come out and Kate reveals she wants to be at the top of Peteâ€™s priority list and for him to stand up to Diane. Meanwhile, the kids help Jackie with her online dating profile.
When Jackie has a drunken encounter with one of Peteâ€™s coworkers at Kate and Peteâ€™s party, Kate and Pete deal with the ensuing awkwardness. Meanwhile, Warren and Bert try to attract more viewers to their live-streaming gum show, and Meg helps Diane with a secret mission.