After failing to get donations on her own terms, Katie gives in to the dark side and teams up with Oliver to bribe rich Westport families to donate big-ticket items for the spring gala. Greg decides to take Taylor and Anna-Kat to a Revolutionary War reenactment which Taylor finds lame until she starts a revolution of her own.

After feeling like their whole world and all of their conversations revolve around kids, Greg and Katie are ecstatic to meet new friends Zach and Courtney, a couple without children. Meanwhile, Anna-Kat coerces Taylor and Oliver into helping her with a storytelling project, which turns out to be a little more grisly than anticipated.

Katie and Greg dislike Taylor's new boyfriend, so they attempt to use reverse psychology to drive a wedge between them, which later backfires. After Spencer's over-the-top vision for Oliver's first date with a girl from his ballet class bombs, Greg helps Oliver make up for it with a romantic gesture.

Katie takes Oliver out of school for a day to help loosen him up after Oliver suffers from a meltdown about something minor. Meanwhile, Anna-Kat takes Greg to the park to help him make new friends.

Katie enlists Angela's legal help to convince Chloe Brown Mueller to sign off on the venue for the Spring Gala, but Angela ends up cozying up to Chloe instead.

When things start to fall apart at the last minute, Katie figures out a new way to make the spring gala a success. Meanwhile, Greg attempts to be a "fun dad" and winds up adopting a dog while Katie is occupied with the gala.

With her new job taking up more of her time, Katie and Greg try to split up parenting duties. Katie over-involves herself in Taylor's social life by trying to keep some distance between Taylor and her boyfriend, Trip, to make sure Taylor is her own person aside from him. Meanwhile, Greg tries to convince Oliver to be honest after overhearing Oliver lie to his friends about his less-than-luxurious summer vacation.

When Katie's mom, Kathryn, comes to town, Katie and Kathryn encourage the kids to make less than favorable decisions: Oliver cheats in shop class and Katie helps him try to get out of it, while Kathryn reassures Taylor that she doesn't need to go to college.

Anna-Kat runs for the Green Chair position in the school election against Chloe Brown Mueller’s daughter, which results in Katie and Chloe turning their kids’ election into a feud of their own. Meanwhile, Greg becomes concerned that Taylor’s new friend Pierce is trying to steal her away from Trip, causing Greg to intervene and scheme to prevent it.

Katie lands the perfect pawn to play on the insecurities of the Westport housewives when she convinces a hot young trophy wife named Harper to volunteer as room mom for Anna-Kat’s class, but she quickly shifts gears when Harper rejects Anna-Kat’s idea for movie night. Meanwhile, Greg enlists the help of the kids to get Katie’s mom, Kathryn, to take an interest in someone other than herself.

Fearing she’s spending too much time at the office and away from the family, Katie volunteers to chaperone Anna-Kat’s school field trip to make up for lost time. Meanwhile, Greg takes a creative approach to parenting when he catches Taylor and Oliver in a lie.

As the Otto family ushers in a new era, Katie and Greg make the emotional decision to sell the family minivan; Daniel suffers a setback that forces him to rethink how to accomplish his goals.

Katie ignores Greg's warning and takes Anna-Kat through a terrifying zombie-themed maze at the annual Halloween carnival. Once inside, Katie quickly regrets her decision and sends Anna-Kat to find help. Meanwhile, Greg has entered a pumpkin carving contest and is ready to go head-to-head against the previous year's winners.

With Katie’s 40th birthday fast approaching, her self-esteem starts to wane. So Greg encourages her to go out and enjoy a night on the town with the girls, even suggesting she leave her wedding ring behind for a night of faux-single, silly fun. Meanwhile, Angela receives devastating news that will turn Doris’ life upside down. While Katie is away, Greg enlists the kids’ help to create a birthday present that is a heartfelt reminder of how much she is loved.

Katie's feud with Chloe Brown Mueller is reignited when Oliver discovers Chloe's attempts to sabotage Katie's lasagna business. Meanwhile, Anna-Kat and Franklin play matchmaker for Principal Amblin in an attempt to secure more privileges.

In an effort to stay connected, Katie and Greg look into activities that they can enjoy as a couple. Meanwhile, Anna-Kat has her own hurdles to overcome when Franklin shines at square dancing and she fails miserably. Plus, Tripp struggles with the idea of Taylor going away to college.

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.

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 reminds Anna-Kat that she is a strong, independent, young woman and encourages her to start standing up for herself when dealing with Taylor. Meanwhile, Oliver feels left out when Greg invites Lonnie, Trip and Franklin to join him at the Historical Guild's latest reenactment.

Against Greg’s better judgment, Katie pushes Taylor to lighten up and participate in her school’s senior prank. Meanwhile, Anna-Kat asks Oliver to give Franklin a makeover so he won’t embarrass himself at a classmate’s party.

After Anna-Kat's big win with The Wildflower Girls, the Ottos head to California for an all-expenses paid family vacation. But when her birthday coincides with their trip, Katie is determined to have a relaxing kid-free day, one where she and Greg are free to do whatever they want. Meanwhile, Taylor loses all her money on Hollywood Boulevard and Anna-Kat is forced into busking to get them out of trouble; and after crashing their trip, Cooper surprises Katie by making her birthday wish come true.

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.

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.

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.

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.

To celebrate the momentous 100th episode milestone of his podcast, Franklin invites Katie and the family to make guest appearances on his show, “Getting Frank with Franklin.” After witnessing his intrusive tactics with Taylor and the others, Katie is determined to keep her interview light and fun but is surprised when her mom Kathryn joins her. Meanwhile, Greg asks Lonnie to be his campaign manager to help strengthen his social media presence.

Katie pushes Cooper to share his passion for the culinary arts and ambition of becoming a chef with his autocratic father, Doyle Bradford. Meanwhile, Greg and Principal Ablin go head-to-head when the election results offer an interesting twist, and the Otto family gets the surprise of a lifetime.