Kate has to watch Bert while both Jackie and Pete are out for the evening, and she can't get Bert to surrender and go to sleep. When he is over-tired in the morning, a frustrated Kate gives him coffee. Bert is energetic at soccer practice that day, but crashes hard later. Meanwhile, Diane uses a little psychological torture to get Warren and Hillary to confess to an accident they had in the house.

When Hillary starts sneaking around on the weekends, Pete overreacts and makes matters worse. Kate tries to take over from Pete and Diane, but she finds that her own parental style needs work. Jackie tries to finagle a jewelry deal with the parent of one of Bert's friends.

When Meg needs Kate's help getting through a breakup, Kate finds herself torn between her obligations as a friend and her responsibilities as a wife and step-mom. Kate struggles to be a good friend to Meg, but when Meg's breakup drama gets to be too much, it leads to a falling out between them. Meanwhile, Warren figures out where his true talents lie when Jackie enlists his help with Bert's Lego project.

Finding it more and more difficult to spend time alone and away from Diane’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 Pete’s priority list and for him to stand up to Diane. Meanwhile, Warren and Hillary help Jackie with her online dating profile.

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.

When Kate and Pete host a party, Jackie crashes and hooks up with Pete’s co-worker Sad Steve, much to Pete’s discomfort. However, when Sad Steve decides to pursue a relationship with Jackie, both Kate and Pete jump on the bandwagon to give young love a boost. Meanwhile, Hillary helps Warren and Bert put together a Gum Show live stream, and Diane faces off with Meg after she posts an unflattering picture of her on Instagram.

When the Harrison household is infected with lice, Diane tries to take charge leaving Kate feeling bulldozed. Jackie and Kate work together to try to prove a point to Diane, but their plan back fires and the lice problem worsens. Meanwhile, Pete plays mediator between Warren and Bert, who are fighting over custody of a teddy bear.

When Kate tries to play matchmaker with Diane and another parent on a field trip, she soon learns that Diane is more challenging to set up than she originally thought. Meanwhile, Jackie decides to nurse Pete back to health and Hillary helps Bert get on his teacher's good side.

Pete, Kate, Diane and Jackie wake up Christmas morning hung-over and the house in complete disaster. They try to piece together the events of last night’s Christmas Eve festivities while also trying to save Christmas for the kids.