Katie tries to help Anna-Kat fit in at school; Taylor and Oliver like the luxe Westport lifestyle.
Greg comes down with the flu and Katie battles exhaustion trying to take care of him and the kids. Later: her exhaustion leads to a confrontation with the school's overbearing school crossing guard.
Katie competes in a zombie run with a neighbor while Greg and Anna-Kat get carried away with the "zombie" theme.
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.
Katie imitates the other moms to help Anna-Kat get invited to a popular girl's birthday party.
Katie's mom visits for Thanksgiving, which puts Katie on edge, but a surprising ally surfaces to help ease the tension.
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?
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,
Viv gets a reluctant Katie to help out with the school Christmas pageant; Greg takes Taylor and Oliver to a nursing home to cheer up the residents.
Anna-Kat has a playdate with a "normal" girl, but Anna-Kat reveals herself to be a kleptomaniac, leading to a conflict between her, Greg and Katie as they try to resolve things.
The Ottos struggle with being stuck at home without power during a snowstorm.
Katie throws a surprise party for Oliver's birthday after he asks for no 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.
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.
Greg befriends fellow history buff but Katie is not happy because he is married to her nemesis.
Katy stops micromanaging to prove a point, but soon realizes everything still runs smoothly. Later: she gets revenge on a local grocery store for selling her defective trash bags.
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 - .
Greg challenges Katie to learn French and set a better example for Taylor, who has developed a habit for quitting school activities.
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.
Anna-Kat wants to walk to the library by herself. Elsewhere: Greg copes with Katie's dating life and Katie is annoyed that Oliver's entitled friend seems to be spending every waking moment at the Ottos.
Anna-Kat develops a fear of water and stops bathing, so her therapists suggests the Ottos take her swimming, but that involves Katie overcoming her fear of wearing a swimsuit in public. Elsewhere: Oliver gives his dad a style makeover.
Katie and Greg enjoy a night on the town with Angela's ex after she helps Greg land a book deal, but Angela's ex soon accuses Katie of being a bad friend.
Katie fakes a pregnancy to get out of mandatory volunteer hours, but things go too far after a baby shower is planned for her.
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.
Katie plans the spring gala her way, despite pressure from Oliver, Greg and Tara. Meanwhile, Oliver is emasculated by his ex-girlfriend, so Greg attempts to teach him how to man up by throwing a successful barbecue.
Taylor dyes her hair blonde without Katie's permission. Meanwhile, Anna-Kat decides she's now a vegetarian; and Greg and Katie help Oliver come to terms with embarrassment after Oliver has a humiliating moment in ballet class.
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.
The Ottos receive a "Boo," which is a Westport tradition of an anonymous note and goodies being left on a neighbor's doorstep, and Katie is absolutely giddy about it, but then they find out it was put at their door by accident.
Greg sides with Anna-Kat about keeping her beloved pet pig, despite Katie's objections, and he even plays dirty to win this battle. Meanwhile, Oliver and Viv compete for the attention of a new neighbor; and Taylor considers dating an older guy.
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, arrives unannounced and nothing goes as intended.
After failing to get donations on her own terms, Katie gives in to the dark side and teams up with Oliver to bribe rich Westport families to donate big-ticket items for the spring gala. Greg decides to take Taylor and Anna-Kat to a Revolutionary War reenactment, which Taylor finds lame until she starts a revolution of her own.
After feeling like their whole world and all of their conversations revolve around kids, Greg and Katie are ecstatic to meet new friends Zach and Courtney, a couple without children. Meanwhile, Anna-Kat coerces Taylor and Oliver into helping her with a storytelling project, which turns out to be a little more grisly than anticipated.
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.
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.
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.
Katie takes Oliver out of school for a day to help loosen him up after Oliver suffers from a meltdown about something minor. Meanwhile, Anna-Kat takes Greg to the park to help him make new friends.
After feeling unappreciated by Greg and the kids, Katie ditches her family for a day at her favorite hideaway spot and leaves Viv in charge of the household. Viv takes this as an opportunity to see if she really is mom material.
Katie takes things too seriously at a field day competition; Greg makes chili for a competition.
The Otto children 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 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 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.
After the passing of a family friend, the Ottos all react differently to the allotment of the deceased’s inheritance
Katie and Greg struggle to resist the urge to micromanage as their children navigate life choices, such as landing your first job, picking out friends and managing homework.
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.
In order to impress the other moms at school, Katie, Taylor and Oliver travel to New York to track down Nathan Fillion at a "Firefly" convention, so Katie can convince him to attend the school's spring gala.
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. Nathan Fillion guest stars as himself.
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 (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.
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's arrival.
The previous "fattest housewife" in Westport gets plastic surgery to lose weight, and 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. In discussing body image with the kids, Katie and her mother, Kathryn, turn out to be bad influences on Anna-Kat and Taylor, unintentionally encouraging them to focus too much on the outward appearance.
Katie learns that the pin code the Ottos use for everything spells out Greg's ex-girlfriend's name, 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.
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.
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.
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.
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.
Katie encourages Greg to splurge on an overnight getaway; Oliver's attempt at a rebellious streak ends in disaster; Taylor comes to the realization that she needs to step up and be a better big sister
Katie panics when Greg is hit with a bout of baby fever; Taylor tricks Oliver into helping her.
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 when Greg becomes fast friends with the newest member of the Westport Historical Guild; 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.
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; 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; 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, 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.
Anna-Kat becomes best friends with Chloe Brown Mueller's daughter; 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; Anna-Kat is crushed when the boy she likes doesn't ask her to the dance; 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 leave the family to fend for itself.
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.
When Greg hosts a meeting for the Westport Historical Guild to welcome back Stan, Katie's homemade lasagna is a huge hit with the guys; Angela and Doris step in to help Oliver with his Teen Help Line interview.
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. Taylor learns her Carnegie Mellon interview is scheduled with famous alumnus and Broadway star Brecken Phillips. Oliver befriends the school recluse.
Katie is determined to help Anna-Kat win top prize in cookie sales against her fellow troop members, The Wildflower Girls; 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. 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.
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 to find her life purpose, she redirects her energy toward Greg and the kids becoming overbearing and controlling. Meanwhile, after sabotaging Greg’s efforts to preserve a historical landmark and putting the future of the Westport Historical Guild in jeopardy, Katie recommends Greg run for city council. And elsewhere, 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. Meanwhile, Greg is forced to separate the kids when Anna-Kat and Franklin both come down with mono. And Cooper feels neglected when Oliver starts spending too much time at the office.
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.
