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.

Katie and Greg enjoy a night on the town with Angela's ex after Celeste, an editor, helps Greg land his first book deal. But Angela, who has asked Katie not to socialize with her former wife, is furious and accuses her of being a bad friend.

When Anna-Kat develops a fear of water and stops bathing, her therapist suggests the Ottos get her to go swimming. But can Katie get over own her fear of wearing a bathing suit in public at the Westport Country Club so she can help her kid out? Meanwhile Oliver gives his dad a style makeover after students at the college give Greg a low "jalapeno" score.

Anna-Kat tells her parents that all she wants for her birthday is a chance to walk the three blocks to the library alone. Can Katie find a way to allow her a little freedom while still keeping tabs on her? Meanwhile, Greg is having a hard time adjusting to the fact that Taylor has a boyfriend, and Katie is annoyed that Oliver's entitled friend Cooper Bradford seems to be spending every waking moment at the Ottos.

When Doris insists that Katie attend the charity polo match she's organizing, Katie invites her crass best friend from college, Billy, to inject some life into the festivities, but Billy grates on the rest of the Ottos.

When Taylor keeps quitting school activities, Greg says that Katie, quite the quitter herself, sets a poor example. He challenges her to finally learn French after quitting lessons so long ago, so she reluctantly enrolls in a college class.

Katie encourages Viv to stand up to her boorish husband, Alan, but things backfire when Viv succeeds and decides to leave him - and move in with the Ottos.

Katie is fed up with the family complaining about her meddling in everything they do, so she decides to back off and let everyone fend for themselves. Expecting total chaos, she's taken aback when everyone seems just fine without her. Meanwhile, incensed that she got sold defective trash bags at the local grocery story, she decides to fight back.

Greg is delighted to finally have made a friend in Westport, fellow history buff Stan, but Katie isn't as happy, especially since Stan is married to her nemesis, Chloe Brown Mueller.

Katie's least favorite holiday is Valentine's Day, but her desire for a low-key approach is overridden by Greg's over-the-top romantic gestures. Meanwhile Oliver has an expensive gift for the girl he's crushing on, and Taylor tries to put one over on her parents in order to attend a Valentine's Day party.

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.

Oliver tells his parents that he's so embarrassed by their modest house that he'd rather not have a birthday party at all. Katie decides to teach him a lesson by ambushing him with a surprise party at home with all his wealthy friends.

The Ottos are trapped at home after a snowstorm knocks out power and blocks the roads. Greg seizes the opportunity to "rough it" at home with the kids. Katie, bitter that she can't go on her planned girls weekend, finds herself making excuses to visit Viv, who is also stranded at home, but with a power generator, free-flowing champagne and cookies.

Katie and Greg are thrilled when Anna-Kat finally has a playdate with a "normal" girl. But Anna-Kat has a little secret: She's a budding kleptomaniac and has taken something from her new friend Penny's home. Greg wants her to return the item and fess up, but Katie disagrees, especially since Penny's mom, Chloe Brown Mueller, is one of Westport's most infamous gossips.

Katie's holiday spirit, never great to begin with, is soured even further when Viv corners her into helping out with the school Christmas pageant. Greg, determined to teach Taylor and Oliver the true meaning of Christmas, takes them to a local nursing home to cheer up the residents, but things don't quite turn out the way he planned.

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.

Katie and Greg throw themselves into PTA politics when they learn that Anna-Kat's special needs teacher, Dr. Ellie, has been cut from the school budget. Greg gets elected to the PTA, and things are looking good, but can Katie keep her mouth in check long enough to win the votes they need?

It's Thanksgiving, but Katie is less-than-thankful that the holiday features a visit from her least-favorite person, her mom Kathryn, a self-centered former Pan Am stewardess. Surprisingly it's Katie's nemesis Viv who helps ease the tension when she invites herself to dinner.

Katie swallows her pride and does the unthinkable, emulating the "perfect" Westport moms by dressing like them and hanging out at the yoga studio, in an attempt to get Anna-Kat a coveted invitation to a popular girl's birthday party.

When Anna-Kat draws a super plus-sized portrait of Katie for the school art show, Katie sets out to retrieve it by any means necessary. Meanwhile, with Katie away, Doris is left in charge of Oliver and Taylor. She's determined to whip them into shape with her Tiger Mom skills, but she may have met her match.

Katie, jealous of Taylor's friendship with neighbor Viv, reluctantly competes in the Westport Halloween "Zombie Run" after she finds out they'll both be running. Meanwhile, Greg and Anna-Kat get a little too much in character for the "zombie" part of the run's obstacle course.

All Katie wants is a good, long nap after the kids keep her up all night. But when Greg gets the flu, she doesn't get a minute to herself. Her exhaustion reaches critical mass with a confrontation with the school's officious crossing guard.

Katie and husband Greg have moved to Westport because the school district there is the best option for their youngest, Anna-Kat. Katie finds herself caught up in helping Anna-Kat fit in more while trying to assure that her older kids, Taylor and Oliver, immediately caught up in the luxe Westport lifestyle, fit in a little less. On top of this, Katie has her own insecurities about her place in their new town. Her 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.