A former party girl marries a much older man knowing that he has "baggage" (two ex-wives and three children between them), and she soon realizes the baggage is going to bring new challenges every day.

When Jackie’s homemade costume nearly ruins Bert’s Halloween, Kate steps in with the costume he wanted, and Bert’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.

Pete tries to get a neighborhood teen to admit he egged Pete’s house last Halloween. Diane steps in to intervene and Warren and Hillary get involved.