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.

With her new job taking up more of her time, Katie and Greg try to split up parenting duties. Katie over-involves herself in Taylor's social life by trying to keep some distance between Taylor and her boyfriend, Trip, to make sure Taylor is her own person aside from him. Meanwhile, Greg tries to convince Oliver to be honest after overhearing Oliver lie to his friends about his less-than-luxurious summer vacation.

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.

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.

When Taylor decides she wants to go to a Halloween party, Greg and Katie disagree on whether or not Taylor can be trusted. Oliver and Cooper anxiously try to prepare for playing a game of Seven Minutes in Heaven with their dates at a separate Halloween event. A pregnant Viv follows Katie around, trying to get help preparing for her baby before it arrives.

After the previous “fattest housewife” in Westport gets plastic surgery to lose weight, Chloe Brown Mueller rubs it in Katie’s face that Katie has now assumed that title. In order to get revenge on Chloe, Katie goes through great lengths to dig up bad photos of Chloe from high school.

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 lands the perfect pawn to play on the insecurities of the Westport housewives when she convinces a hot young trophy wife named Harper to volunteer as room mom for Anna-Kat’s class, but she quickly shifts gears when Harper rejects Anna-Kat’s idea for movie night. Meanwhile, Greg enlists the help of the kids to get Katie’s mom, Kathryn, to take an interest in someone other than herself.

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.

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.

Greg’s insistence on doing the family’s taxes prompts Katie to take matters into her own hands. Meanwhile, Oliver and Anna-Kat join forces in an attempt to win a popular radio contest; and when Taylor finally sees Pierce’s true colors, the family bands together to help her pull off an over-the-top apology for Trip.

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.

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.

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.

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.

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 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.

In order to avoid buying Anna-Kat a cellphone, Katie makes a pact with the girls that she and Taylor can go an entire day without using their phones. Meanwhile, disappointed with Greg’s advice, Oliver seeks the guidance of an old friend.

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.

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.

Much to Katie’s dismay, Anna-Kat becomes best friends with Chloe Brown Mueller’s daughter, Penny. When Katie takes extreme measures to avoid Chloe and keep the girls apart, Anna-Kat and Penny are forced to take matters into their own hands. Meanwhile, Greg encourages Oliver to be honest with his girlfriend and not hide his passion for ballet.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 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.

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 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.

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.

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.

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.

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.

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 goes to great lengths to appease Principal Ablin in order to ensure Taylor graduates high school. Meanwhile, Greg finishes ghost writing the final chapter of Lonnie's book. And while Oliver is devastated to learn Cooper's family will be moving out of Westport, Anna-Kat tells Franklin she is ready to venture outside her comfort zone and plans to attend sleep-away camp during summer break.

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.

Katie is taken aback when she learns Taylor's boyfriend Trip has been spending the night. Greg is forced to separate the kids when Anna-Kat and Franklin both come down with mono. And when Oliver starts spending too much time at the office, Cooper begins to feel neglected.

With Anna-Kat and Franklin home with mono, Katie seizes the opportunity to use them as the backdrop for her mommy vlog. And when Taylor's first college paper comes back with an A, Greg questions her TA's intentions. Meanwhile, Cooper helps Oliver renovate the basement.

Katie pushes Anna-Kat and Franklin to take a risk and try an activity outside their comfort zone in order to create new content for her mommy vlog. Meanwhile, Oliver is convinced taking performance-enhancing drugs will help him ace his SATs. And after bonding with her TA over an art exhibit, Taylor begins to wonder if Trip is the right guy for her.

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.

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.

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 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.

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.

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 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 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.