After the second-fattest housewife in Westport moves out of the Otto family's neighborhood, Katie tries to ensure that another heavyset woman moves into the home to avoid moving up to the #2 spot herself.
Greg comes down with the flu and Katie battles exhaustion trying to take care of him and the kids. Later: her exhaustion leads to a confrontation with the school's overbearing school crossing guard.
Upset over Taylor spending so much time with new neighbor Viv, Katie tells Viv that she plans to participate in the annual Westport Zombie Run, with the intention of beating Viv and winning her daughter back.
When Anna-Kat submits a family drawing for a local children's art fair that portrays her mom as huge and round, Katie goes to great lengths to get it replaced with something else. While she is out, Katie leaves Doris in charge of the kids, and they don't react well to her much stricter parenting style. Meanwhile, Greg has an idea for an article that he thinks will finally earn him tenure, but his writing routine is constantly interrupted by family members.
Katie tries to fit in with the other Westport moms in order to get Anna-Kat invited to a popular girl's birthday party. When Anna-Kat still isn't invited, Katie vents to Angela and Doris, and realizes her daughter doesn't need a bunch of friends, just a couple of close ones. Elsewhere, Greg tries to convince Taylor that she can't get by on her athletic ability alone, while Oliver complains about a flawed polo shirt that his mom bought at an outlet store.
Katie's mother Kathryn shows up for Thanksgiving, and typically wants to be the center of attention. Just prior, Katie met with Anna-Kat's teacher, who said Anna-Kat is more anxious than normal, and Katie realizes her own anxiety over her mother is affecting her daughter. Also, an unwanted guest crashes the Otto family Thanksgiving.
Katie and Greg throw themselves into PTA politics when they learn that Anna-Kat's special needs teacher, Dr. Ellie, has been cut from the school budget. Greg gets elected to the PTA, and things are looking good, but can Katie keep her mouth in check long enough to win the votes they need?
As Katie tries to keep better tabs on what her children are doing, Oliver tells Greg that he's secretly taking cotillion classes. With the cotillion dance event coming soon, Oliver asks Dad to keep the secret from Katie, fearing that Mom will show up at the dance and embarrass him.
When Katie angrily refuses Viv's help in decorating the Otto house for Christmas and is reluctant to help Viv with the school's Christmas show, Anna-Kat sees her mother as Krampus, the demon who punishes misbehaving children during the holidays. Meanwhile, Greg tries to teach Taylor and Oliver about the true meaning of Christmas by forcing them to visit elderly residents at an assisted living facility, but it backfires.
The Ottos are surprised when Anna-Kat gets invited to a playdate with the daughter of Chloe Brown Mueller, a known gossip who posts ratings of her daughter's playdates on social media. The playdate goes surprisingly well, but Katie and Greg later find that Anna-Kat stole a silver candlestick from the Mueller house. Elsewhere, Oliver is always on the phone and Taylor is convinced he has a new girlfriend. She tails him after one of the calls and finds something entirely different going on.
The family camping trip Greg has planned is cancelled when a snowstorm knocks out power to the Otto home, so he uses the blackout to set up a "camping at home" experience. Katie takes refuge at Viv's house, which has backup generators. After discovering that Viv is lying about her husband's affection to keep up appearances, Katie also learns how Viv's first marriage ended and realizes she has to share Greg's interests once in a while.
Oliver insists he doesn't want a birthday party with friends because he's embarrassed over the size and amenities in the Otto home, but Katie and Greg throw one anyway with an escape room. Despite some problems, the party winds up working in Oliver's favor. Meanwhile, Taylor starts to get romantic with her new math tutor, a classmate, which angers the boy's adoptive mom.
The Ottos return home to find their house has been put up for sale. As they cannot afford to buy or rent any other home in the Westport area, they are forced to consider moving. This thrills Katie, until she sees how much Greg and the kids want to stay. Katie and Greg learn that the man who wants to sell the house did not get permission to do so from the actual owner (his mother). They track down the owner, Linda Smith, who tells them they can stay and pay their current rent as long as they want.
Katie's least favorite holiday is Valentine's Day, but her desire for a low-key approach is overridden by Greg's over-the-top romantic gestures. Meanwhile Oliver has an expensive gift for the girl he's crushing on, and Taylor tries to put one over on her parents in order to attend a Valentine's Day party.
Katie finds it hard to put aside her ongoing feud with Chloe Brown Mueller when Greg becomes good friends with Chloe's husband, Stan. Meanwhile, Taylor learns that Anna-Kat is being bullied at school, but the advice she gives her little sister turns Anna-Kat into the bully.
After her family confesses to giving Katie the unflattering nickname "Colonel Beatrix Von Beige Underpants Control Freak", she tries to back off and let them run their own lives for a while. It seems she isn't needed when Oliver helps Anna-Kat sell bunches of panda paintings for charity and Greg helps Taylor find a sporting activity she can do while her ankle heals. But it's not long before all ask for Katie's help again. Meanwhile, Katie goes to war with big box store manager Ian over defective garbage bags.
When Viv proclaims her husband Alan has cut off her credit cards, Katie suggests she stand up to him, despite Greg's advice that she stay out of other people's marriages. The result is that Viv leaves Alan and moves in with the Ottos. Meanwhile, Greg tries to find a way to discipline Oliver and Taylor for constantly leaving cupboards and drawers open.
Taylor quits synchronized swimming and takes up drama. When she soon wants to quit drama, Greg and Katie remind her of the "Otto Motto" which is "never give up". This backfires on Katie when Greg reminds her of all the things she started and quit, including learning French in advance of their dream vacation to Paris. Meanwhile, Oliver has put together an attainment board with a collage of shirtless male models and also takes up ballet, causing Katie, Doris and Angela to think he might be gay.
When Doris insists that Katie attend the charity polo match she's organizing, Katie invites her crass best friend from college, Billy, to inject some life into the festivities, but Billy grates on the rest of the Ottos.
Anna-Kat wants to walk to the library by herself. Elsewhere: Greg copes with Katie's dating life and Katie is annoyed that Oliver's entitled friend seems to be spending every waking moment at the Ottos.
Anna-Kat develops a fear of water and stops bathing, so her therapists suggests the Ottos take her swimming, but that involves Katie overcoming her fear of wearing a swimsuit in public. Elsewhere: Oliver gives his dad a style makeover.
Katie and Greg enjoy a night on the town with Angela's ex after she helps Greg land a book deal, but Angela's ex soon accuses Katie of being a bad friend.
Katie fakes a pregnancy to get out of mandatory volunteer hours, but things go too far after a baby shower is planned for her.