Katie Otto, a confident, unapologetic wife and mother of three, raises her flawed family in the wealthy town of Westport, Connecticut, filled with "perfect" mommies and their "perfect" offspring. Katie's perfectly imperfect world is upended when her neighbor's decision to move notches her up from her ideal social standing and sets her on a path to ensure that doesn't happen, regardless of the consequences.
Frustrated by the lack of appreciation for all she does, Katie decides to leave the family to fend for itself.
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 plans a "friend date" in hopes of reconnecting with Taylor; Greg attends self-help seminar with Oliver; Anna-Kat takes extreme measures to secure her place as Katie's favorite child.Watch Now:Amazon
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 strives to keep her long-separated parents apart when her father arrives in time to surprise the Otto family for Christmas. Anna-Kat does her best to help Trip win Taylor back but has a hard time getting past a very persistent Pierce. Meanwhile, Oliver thinks no one will remember him as the mask-wearing villain in the school's production of "The Nutcracker" but quickly takes center stage when a series of mishaps damages his costume.
Oliver and Taylor stumble through their love lives, making Katie miss the spontaneity and unpredictability of being young and in love. Meanwhile, Kathryn's plan to soothe Oliver's heartbreak backfires when she tracks down an old boyfriend, Dan, and he is not as she remembers. At the same time, Anna-Kat makes strides at school when Franklin is stuck at home with the chickenpox, forcing her to make a new friend.Watch Now:Amazon
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 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.
When Katie forgets Greg's birthday, she attempts to make up for it by pulling together a last-minute dinner party.Watch Now:Amazon
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.Watch Now:AmazoniTunes
Katie tries to help Anna-Kat fit in at school; Taylor and Oliver like the luxe Westport lifestyle.Watch Now:Amazon
When Katie gets sick, Greg enlists Kathryn's help in taking care of the kids; Taylor gets a taste of her own medicine when she tries to help an unruly Katie.Watch Now:Amazon
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.
When Katie's mom, Kathryn (Wendie Malick), 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.Watch Now:Amazon
Katie must mend fences with the Westport moms by volunteering to run the school's spring gala. Meanwhile, Katie confronts Oliver's belittling ballet teacher; and Taylor and Greg disagree about the necessity of college.Watch Now:Amazon
Katie is worried that the launch of Greg's new book might go poorly, so she enlists Angela and Doris to write positive reviews of the book online to boost his confidence. When the book unexpectedly does exceedingly well, Greg buys a new car without consulting Katie.Watch Now:Amazon
A lice infestation occurs in the Otto household thanks to Anna-Kate, and Katie uses this as an excuse to bond with Taylor. Meanwhile, Greg and Oliver camp in the backyard, but Oliver keeps ditching their campout to hang with their sleazy new neighbor.Watch Now:Amazon
Katie panics when Greg is hit with a bout of baby fever; Taylor tricks Oliver into helping her.Watch Now:Amazon
Greg's insistence on doing the family's taxes prompts Katie to take matters into her own hands; Oliver and Anna-Kat join forces in an attempt to win a popular radio contest; Taylor finally sees Pierce's true colors.
When Doris goes into labor and Katie heads to the hospital to be with her, the Ottos struggle to be in the same place at the same time in order to open their Christmas presents together, as is the Otto family tradition. Meanwhile, Taylor coaches Oliver on the best way to ask out a crush, starting with the gift shop clerk.Watch Now:Amazon
Fearing she's spending too much time at the office, Katie volunteers to chaperone Anna-Kat's school field trip; Greg takes a creative approach to parenting when he catches Taylor and Oliver in a lie.Watch Now:Amazon