Frustrated by the lack of appreciation for all she does, Katie decides to go “full Westport” and leaves the family to fend for themselves. Katie’s plan quickly backfires when the kids seem to be doing just fine, leaving Greg to suffer the brunt of her absence.

Greg ropes Katie into a double date with Principal Ablin and Maria in an attempt to further his political aspirations. Meanwhile, Anna-Kat’s newfound popularity at school proves to be overwhelming.

Katie and Tami make fast friends with J.D., a luxury hotel manager whose promise of access to complimentary hotel rooms around the world sounds incredibly enticing. However, Katie’s travel fantasy comes to a screeching halt when she learns J.D. is an aspiring first-time father who’s counting on her for parenting guidance.

Katie pushes Anna-Kat and Franklin to take a risk and try an activity outside their comfort zone in order to create new content for her mommy vlog. Meanwhile, Oliver is convinced taking performance-enhancing drugs will help him ace his SATs. And after bonding with her TA over an art exhibit, Taylor begins to wonder if Trip is the right guy for her.

Katie tries to help Anna-Kat fit in at school. Taylor and Oliver like the luxe Westport lifestyle.

Katie goes to great lengths to appease Principal Ablin in order to ensure Taylor graduates high school. Meanwhile, Greg finishes ghost writing the final chapter of Lonnie's book. And while Oliver is devastated to learn Cooper's family will be moving out of Westport, Anna-Kat tells Franklin she is ready to venture outside her comfort zone and plans to attend sleep-away camp during summer break.

With Anna-Kat and Franklin home with mono, Katie seizes the opportunity to use them as the backdrop for her mommy vlog. And when Taylor's first college paper comes back with an A, Greg questions her TA's intentions. Meanwhile, Cooper helps Oliver renovate the basement.

When Katie’s mentor and dear friend Tami moves to Westport, Katie wastes no time introducing her to her “A Real Mother” vlog viewers. Meanwhile, Taylor discovers Greg has been keeping an entertaining secret.

Without her lasagna business to keep her preoccupied, Katie feels like her life is once again off course. As she searches for purpose, she redirects her energy toward Greg and the kids becoming overbearing and controlling. Franklin challenges an older boy to a duel in an effort to win back Anna-Kat's affections.

Katie goes overboard in her efforts to help J.D. become a father. Meanwhile, after a brush with the law, Greg worries Taylor may be a political liability.

Doris insists that Katie attend the charity polo match she's organizing.

While Greg enlists Oliver and Anna-Kat’s help to drum up new recruits for the Westport Historical Guild, Katie does her best to support Taylor’s dreams of becoming the next American Idol.

Katie is taken aback when she learns Taylor's boyfriend Trip has been spending the night. Greg is forced to separate the kids when Anna-Kat and Franklin both come down with mono. And when Oliver starts spending too much time at the office, Cooper begins to feel neglected.

Katie and Greg secretly put Kathryn through a series of tests to see if she would make a good guardian for Anna-Kat in the unlikely event something should happen to them. Meanwhile, after tracking down J.D.’s potential egg donors, Tami and Katie scheme to learn more about them.

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.

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.

Viv asks Katie to take Violet for the night so she and Alan can discuss reconciling but is caught off guard when Greg is hit with a bout of baby fever. Meanwhile, Taylor tricks Oliver into helping her when Luther eats an expensive pair of earrings.

Katie begins to feel like the third wheel when the topic at second breakfast starts revolving solely around Angela and Doris’ new relationships. Meanwhile, Greg struggles with Anna-Kat’s newfound independence.

Katie plays matchmaker by impersonating Oliver on his social media account to win over a girl. Meanwhile, Lonnie helps Greg dig up dirt on his political rival.

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 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.

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,

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.

Greg befriends fellow history buff Stan, but Katie is less than pleased, especially considering he is married to her nemesis, Chloe Brown Mueller.