When Anna-Kat draws an unflattering portrait of Katie for the school art show, Katie plans to retrieve it before anyone can see it; Doris is left in charge of Oliver and Taylor.

When Anna-Kat brings home a lice infestation, Katie uses it to force bonding time with Taylor. Greg attempts to bond with Oliver (and avoid lice) by camping in the backyard, but Greg becomes concerned when Oliver keeps ditching their campout to be with their new sleazy neighbor named Spencer.

When Doris goes into labor and Katie heads to the hospital to be with her, the Ottos struggle to be in the same place at the same time in order to open their Christmas presents together, as is the Otto family tradition. Meanwhile, Taylor coaches Oliver on the best way to ask out a crush, starting with the gift shop clerk.

After spending years as a full-time mom, Katie goes back to work as a party planner, which brings new challenges of balancing home and work life into the mix.

After the previous “fattest housewife” in Westport gets plastic surgery to lose weight, Chloe Brown Mueller rubs it in Katie’s face that Katie has now assumed that title. In order to get revenge on Chloe, Katie goes through great lengths to dig up bad photos of Chloe from high school.

As Oliver and Taylor stumble through their love lives, Katie begins to miss the spontaneity and unpredictability of being young and in love. Meanwhile, Kathryn’s plan to soothe Oliver’s heartbreak backfires when she tracks down an old boyfriend, Dan, and he is not as she remembers. At the same time, Anna-Kat makes strides at school when Franklin is stuck at home with the chickenpox, forcing her to make a new friend.

Against her husband's wishes, Katie sets out to play matchmaker for British Greg. Meanwhile, Oliver goes along with a rumor at school about his sexual identity to help a classmate feel accepted.