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.

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.