Episode 1
Graduation
October 28, 2020
Episode 3
Coupling
November 18, 2020
Episode 4
Homeschool Sweet Homeschool
November 25, 2020
Episode 5
Kids These Days
December 2, 2020
Episode 6
Mother's Little Helper
January 13, 2021
Episode 7
Under Pressure
January 27, 2021
Episode 8
Encourage, Discourage
February 3, 2021
Episode 9
The Heist
February 10, 2021
Episode 10
Getting Frank with the Ottos
February 24, 2021
Episode 11
The Guardian
March 3, 2021
Episode 12
How Oliver Got His Groove Back
March 24, 2021
Episode 13
The Election
March 31, 2021
Episode 1
The Minivan
September 27, 2019
Episode 2
Bed, Bath & Beyond Our Means
October 4, 2019
Episode 3
Bigger Kids, Bigger Problems
October 11, 2019
Episode 5
The Maze
October 25, 2019
Episode 6
Girls' Night Out
November 1, 2019
Episode 7
Flavor of Westport
November 15, 2019
Episode 8
Women in Business
November 22, 2019
Episode 9
Hip to Be Square
November 29, 2019
Episode 10
The Bromance Before Christmas
December 6, 2019
Episode 11
One Step Forward, Three Steps Back
January 17, 2020
Episode 12
Wildflower Girls
January 24, 2020
Episode 13
The Great Cookie Challenge
January 31, 2020
Episode 14
A Very English Scandal
March 18, 2020
Episode 15
In My Room
March 25, 2020
Episode 16
The Battle for Second Breakfast
April 1, 2020
Episode 17
All Is Fair in Love and War Reenactment
April 15, 2020
Episode 18
Senior Prank
April 22, 2020
Episode 1
Mom Guilt
September 26, 2018
Episode 2
Here We Go Again
October 3, 2018
Episode 3
Cheaters Sometimes Win
October 10, 2018
Episode 4
Enemies: An Otto Story
October 17, 2018
Episode 5
Trust Me
October 24, 2018
Episode 6
Body Image
October 31, 2018
Episode 7
The Code
November 7, 2018
Episode 8
Trophy Wife
November 28, 2018
Episode 9
Highs and Lows
December 5, 2018
Episode 10
Saving Christmas
December 12, 2018
Episode 11
The Things You Do
February 5, 2019
Episode 12
Disconnected
February 12, 2019
Episode 13
Mo' Money, Mo' Problems
February 19, 2019
Episode 14
Baby Crazy
February 26, 2019
Episode 15
American Idol
March 19, 2019
Episode 16
Insta-Friends
March 26, 2019
Episode 17
Liar Liar, Room on Fire
April 9, 2019
Episode 18
Phone Free Day
April 16, 2019
Episode 19
Grandma's Way
April 23, 2019
Episode 20
Field Trippin'
April 30, 2019
Episode 21
Locked in the Basement
May 7, 2019
Episode 23
A Mom's Parade
May 21, 2019
Episode 1
Back to School
September 27, 2017
Episode 2
Boar-Dain
October 4, 2017
Episode 3
The Uprising
October 11, 2017
Episode 4
The Lice Storm
October 18, 2017
Episode 5
Boo-Who?
October 25, 2017
Episode 6
The Pig Whisperer
November 1, 2017
Episode 7
Family Secrets
November 15, 2017
Episode 8
Gala Auction
November 29, 2017
Episode 9
The Couple
December 6, 2017
Episode 10
Blue Christmas
December 13, 2017
Episode 11
Blondetourage
January 3, 2018
Episode 12
Selling Out
January 10, 2018
Episode 13
The Anniversary
January 17, 2018
Episode 14
Midlife Crisis
January 24, 2018
Episode 15
The Mom Switch
January 24, 2018
Episode 16
Field Day
February 28, 2018
Episode 17
All Coupled Up
March 7, 2018
Episode 19
It's Hard to Say Goodbye
March 21, 2018
Episode 20
The Inheritance
April 4, 2018
Episode 21
It's Not You, It's Me
April 11, 2018
Episode 22
Sliding Sweaters
May 2, 2018
Episode 23
Finding Fillion
May 9, 2018
Episode 24
The Spring Gala
May 16, 2018
Episode 3
Westport Zombies
October 25, 2016
Episode 4
Art Show
November 1, 2016
Episode 5
The Snub
November 15, 2016
Episode 6
The Blow-Up
November 22, 2016
Episode 7
Power Couple
November 29, 2016
Episode 8
Westport Cotillion
December 6, 2016
Episode 9
Krampus Katie
December 13, 2016
Episode 10
The Playdate
January 3, 2017
Episode 11
The Snowstorm
January 10, 2017
Episode 12
Surprise
January 17, 2017
Episode 13
Then and Now
February 7, 2017
Episode 14
Time for Love
February 14, 2017
Episode 15
The Man Date
February 21, 2017
Episode 17
Other People's Marriages
March 14, 2017
Episode 18
The Otto Motto
April 4, 2017
Episode 19
The Polo Match
April 11, 2017
Episode 22
Dude, Where's My Napkin?
May 9, 2017
Episode 23
Can't hide It Anymore
May 16, 2017