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.

Anna-Kat tells her parents that all she wants for her birthday is to walk to the library alone.

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.

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.

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.

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.

The Otto children are beginning to experience struggles in their love lives after jumping into the dating world: Oliver is forced to choose between his girlfriend and his friend Cooper who come from two different worlds; Greg must play the “bad cop parent” to halt the PDA between Taylor and Trip; and Anna-Kat tries to make her relationship with Franklin official, without his consent.

Katie wants to prove to the Westport moms that she is fully capable of competing at Field Day at Anna-Kat’s school, but she ends up taking the competition a little too seriously. Greg enlists Taylor’s boyfriend, Trip, to help him make the family recipe for chili in a local competition, which makes Taylor and Oliver jealous.

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 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.

When Anna-Kat draws an unflattering portrait of Katie for the school art show, Katie plans to retrieve it before anyone can see it; Doris is left in charge of Oliver and Taylor.

Greg befriends fellow history buff Stan, but Katie is less than pleased, especially considering he is married to her nemesis, Chloe Brown Mueller.

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.

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 “jalapeño” score.

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.

Greg plays dirty to convince Katie to let them keep Anna-Kat's beloved pet pig; Oliver and Viv compete for the attention of a new neighbor; Taylor considers leaving her boyfriend.

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?

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.

Katie struggles with Taylor and Anna-Kat’s defiance, as Anna-Kat decides she’s now a vegetarian (under the influence of Tara Summers) and Taylor dies her hair blonde without Katie’s permission. Greg and Katie help Oliver come to terms with embarrassment after Oliver has a humiliating moment in ballet class.

Katie and Greg struggle to help the kids accept loss as a family friend suddenly passes away and as their pet pig, Hans Gruber, must be returned to his natural habitat.

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.

Greg makes big plans to impress his parents when they visit for Thanksgiving; but his vision is shattered when his neighbor Spencer and Katie’s mom, Kathryn, arrive unannounced and nothing goes as intended.

Katie lets everyone fend for themselves and is a bit surprised when they don't seem to need her.

Katie tries to fit in with the other Westport moms in order to get Anna-Kat invited to a popular girl's birthday party. When Anna-Kat still isn't invited, Katie vents to Angela and Doris, and realizes her daughter doesn't need a bunch of friends, just a couple of close ones. Elsewhere, Greg tries to convince Taylor that she can't get by on her athletic ability alone, while Oliver complains about a flawed polo shirt that his mom bought at an outlet store.

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

The Ottos struggle with being stuck at home without power during a snowstorm.

Greg blames Katie for setting a bad example when Taylor quits her school activities.

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.

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.

Katie's mother Kathryn (Wendie Malick) shows up for Thanksgiving, and typically wants to be the center of attention. Just prior, Katie met with Anna-Kat's teacher, who said Anna-Kat is more anxious than normal, and Katie realizes her own anxiety over her mother is affecting her daughter. Also, an unwanted guest (Viv) crashes the Otto family Thanksgiving.

With the kids away at the school dance, Katie and Greg look forward to a romantic evening alone; but Anna-Kat is crushed when the boy she likes doesn’t ask her to the dance, and Oliver begins to panic when the town psychic’s predictions begin to come true.

Frustrated by the lack of appreciation for all she does, Katie decides to go “full Westport” and leaves the family to fend for themselves. Katie’s plan quickly backfires when the kids seem to be doing just fine, leaving Greg to suffer the brunt of her absence.

Katie goes overboard in her efforts to help J.D. become a father. Meanwhile, after a brush with the law, Greg worries Taylor may be a political liability.

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.

While 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.

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 plans a “friend date” in hopes of reconnecting with Taylor and encourages Greg to attend self-help guru Johnny Diamond’s seminar with Oliver. Meanwhile, Anna-Kat takes extreme measures to secure her place as Katie’s favorite child.

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.

Katie plays matchmaker by impersonating Oliver on his social media account to win over a girl. Meanwhile, Lonnie helps Greg dig up dirt on his political rival.

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.

Katie is worried that the launch of Greg's new book might go poorly, so she enlists Angela and Doris to write positive reviews; when the book unexpectedly does exceedingly well, Greg buys a new car without consulting Katie.

As Oliver and Taylor stumble through their love lives, Katie begins to 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.

When Katie forgets Greg’s birthday, she attempts to make up for it by pulling together a last-minute dinner party; but when the evening falls flat, Katie gets caught up in a series of lies, leading her friends to believe that she and Greg are in marriage counseling.

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.

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.

Katie strives to keep her long-separated parents apart when her father, Marty, 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.

Katie and Tami make fast friends with J.D., a luxury hotel manager whose promise of access to complimentary hotel rooms around the world sounds incredibly enticing. However, Katie’s travel fantasy comes to a screeching halt when she learns J.D. is an aspiring first-time father who’s counting on her for parenting guidance.

Katie tries to help Anna-Kat fit in at school. Taylor and Oliver like the luxe Westport lifestyle.

When Katie gets sick, Greg enlists Kathryn's help in taking care of the kids, but Kathryn leaves the kids to fend for themselves while she entertains an old high school boyfriend. Meanwhile, Taylor gets a taste of her own medicine when she tries to help an unruly Katie.

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.

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.

When Katie starts her day in a bad mood, the Ottos come together to cheer her up; but in an alternate reality and in a different sweater, Katie starts her day in a good mood and the family comes together to cheer up Greg.

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.

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.

After discovering that the four digit pin code the Otto family uses for everything spells out Greg’s ex-girlfriend’s name, Katie gets upset and retaliates by dragging out old gifts from past boyfriends. Meanwhile, the kids’ current love lives take a hit as Taylor and Trip argue over her relationship with Pierce; and Oliver and Gina’s relationship goes south when they both apply for a ballet scholarship that only one of them gets.

Katie feels left out and slightly jealous when Greg becomes fast friends with the newest member of the Westport Historical Guild. Meanwhile, Oliver fears Cooper is ditching him when he sees on social media that Cooper lied about his weekend plans.

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.

Taylor enlists Oliver to help her carry out a scheme so she can ditch her less cool friend Ellen and go to a concert with her "blondetourage." Meanwhile, Katie is devastated when Anna-Kat doesn't need her as much anymore, which causes Katie to make some poor and desperate parenting decisions.

Viv asks Katie to take Violet for the night so she and Alan can discuss reconciling but is caught off guard when Greg is hit with a bout of baby fever. Meanwhile, Taylor tricks Oliver into helping her when Luther eats an expensive pair of earrings.

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.

After spending years as a full-time mom, Katie goes back to work as a party planner, which brings new challenges of balancing home and work life into the mix.

After coming to terms with the fact that she must share her work bonus with Greg, Katie encourages him to live a little and the two decide to splurge on an overnight getaway. Meanwhile, Oliver’s attempt at a rebellious streak ends in disaster; and after letting Anna-Kat down, Taylor comes to the realization that she needs to step up and be a better big sister.