Episode 1
The Minivan
September 27, 2019
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.
Episode 2
Bed, Bath & Beyond Our Means
October 4, 2019
Katie's life is turned upside down when her notoriously elusive boss Whitney pops into town and promotes Katie; a colleague's death pushes Greg toward an existential crisis.
Episode 3
Bigger Kids, Bigger Problems
October 11, 2019
When Anna-Kat's school lunch lady refuses to make simple eco-friendly changes in the school cafeteria, Greg puts on a show highlighting the importance of recycling with his friend and fellow environmentalist Bill Doty.
Episode 4
Lasagna
October 18, 2019
Greg hosts a meeting for the Westport Historical Guild to welcome back Stan, and Katie's homemade lasagna is a huge hit with the guys. After Stan makes several trips back for seconds and begins spending an inordinate amount of time at the Otto house, Chloe Brown Mueller becomes convinced that Katie and Stan must be having an extra-marital affair. Meanwhile, Angela and Doris step in to help Oliver with his Teen Help Line.
Episode 5
The Maze
October 25, 2019
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.
Episode 6
Girls' Night Out
November 1, 2019
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.
Episode 7
Flavor of Westport
November 15, 2019
Katie teams up with Oliver in hopes of growing her lasagna-making endeavor from hobby to serious business venture. Meanwhile, a bout of writer's block forces Greg to look at new career opportunities. When a young YouTube sensation enlists Greg's help to ghostwrite his memoir, Greg is pushed out of his comfort zone.
Episode 8
Women in Business
November 22, 2019
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.
Episode 9
Hip to Be Square
November 29, 2019
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.
Episode 10
The Bromance Before Christmas
December 6, 2019
Katie looks forward to sharing her favorite childhood Christmas tradition with Taylor, but a surprise visit from her mom threatens her holiday cheer; Greg is blindsided by Katie's good intentions; Oliver and Anna-Kat break a family heirloom.
Episode 11
One Step Forward, Three Steps Back
January 17, 2020
When Anna-Kat begins exhibiting past OCD behaviors, Katie and Greg worry their busy schedules are disrupting the family. Meanwhile, Oliver fields a call at the Teen Help Line center that rattles him. And, Taylor and Trip attempt a trial run at being in a long-distance relationship.
Episode 12
Wildflower Girls
January 24, 2020
Katie grows concerned when Anna-Kat is invited to join Westport's elite scout troop, The Wildflower Girls. Meanwhile, Taylor learns her Carnegie Mellon interview is scheduled with famous alumnus and Broadway star Brecken Phillips ; and, Oliver befriends the school recluse, Trevor.
Episode 13
The Great Cookie Challenge
January 31, 2020
When Katie learns that the top prize is an all-expense paid vacation, she doubles her efforts to help Anna-Kat win top prize in cookie sales against her fellow troop members, The Wildflower Girls. Meanwhile, Oliver's attempt to help a student he befriends through the Teen Help Line center backfires.
Episode 14
A Very English Scandal
March 18, 2020
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.
Episode 15
In My Room
March 25, 2020
Katie finds an old piece of furniture in the basement and sets out to recreate her and Greg's first apartment, reminiscent of a time when life was simpler. Meanwhile, Greg enjoys an unexpected benefit of being the victim of Lonnie's relentless practical jokes.
Episode 16
The Battle for Second Breakfast
April 1, 2020
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.
Episode 17
All Is Fair in Love and War Reenactment
April 15, 2020
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.
Episode 18
Senior Prank
April 22, 2020
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.
Episode 19
Vacation!
May 6, 2020
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.
Episode 20
Prom
May 13, 2020
Katie confronts a classmate's mom when she suspects Anna-Kat is being bullied at school. Meanwhile, Taylor sets out to complete the final item on her life skills checklist - teaching Greg to shoot a three-pointer - so that she can attend her senior prom. At the same time, Oliver is sympathetic when a caller at the Teen Help Line confides that no one asked her to prom.
