Greg comes down with the flu and Katie battles exhaustion trying to take care of him and the kids. Her exhaustion leads to a confrontation with the school's overbearing school crossing guard.
Katie, jealous of Taylor’s friendship with neighbor Viv, reluctantly competes in the Westport Halloween “Zombie Run” after she finds out they’ll both be running. Meanwhile, Greg and Anna-Kat get a little too much in character for the “zombie” part of the run’s obstacle course.
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.
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 (Wendie Malick) 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 (Viv) 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?
Oliver is secretly taking dancing and manners classes in hopes of getting the girl he likes to go to the Westport Cotillion with him. He asks for his dad’s help in keeping this all secret from Katie, afraid that she’ll interfere, but that’s easier said than done,
Katie's holiday spirit, never great to begin with, is soured even further when Viv corners her into helping out with the school Christmas pageant. Greg, determined to teach Taylor and Oliver the true meaning of Christmas, takes them to a local nursing home to cheer up the residents, but things don't quite turn out the way he planned.
Katie and Greg are thrilled when Anna-Kat finally has a playdate with a "normal" girl. But Anna-Kat has a little secret: She's a budding kleptomaniac and has taken something from her new friend Penny's home. Greg wants her to return the item and fess up, but Katie disagrees, especially since Penny's mom, Chloe Brown Mueller, is one of Westport's most infamous gossips.
Oliver tells his parents that he's so embarrassed by their modest house that he'd rather not have a birthday party at all. Katie decides to teach him a lesson by ambushing him with a surprise party at home with all his wealthy friends.
The Ottos face the prospect of leaving Westport when their house is put up for sale. No one wants to leave except Katie, who seems determined to move on despite some fun memories of her family's time there.
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.
When Anna-Kat develops a fear of water and stops bathing, her therapist suggests the Ottos get her to go swimming. But can Katie get over own her fear of wearing a bathing suit in public at the Westport Country Club so she can help her kid out? Meanwhile Oliver gives his dad a style makeover after students at the college give Greg a low “jalapeño” score.
Katie and Greg enjoy a night on the town with Angela’s ex after Celeste, an editor, helps Greg land his first book deal. But Angela, who has asked Katie not to socialize with her former wife, is furious and accuses her of being a bad friend
Katie has been avoiding the mandatory volunteer hours at her kids’ schools all year. But when the other moms pressure her, she hits on a genius excuse after wearing a fake pregnancy “empathy” bump leads everyone to think she is pregnant. But things soon get out of hand after her former frenemies plan a baby shower for her.
