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.

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.

Katie’s efforts to get more time for herself backfire when she is forced to mend fences with the Westport moms by volunteering to run the school’s spring gala. Meanwhile, Oliver proves to Katie that his passion for ballet is genuine, inspiring her to confront his belittling teacher and stick up for him. Taylor and Greg disagree over whether or not she needs to go to college while he teaches her how to drive.

Despite pressure from Oliver, Greg and her rival, Tara, Katie insists she’s going to plan the Spring Gala her way. After Oliver is emasculated by his ex-girlfriend, Greg attempts to teach Oliver how to “man up” by throwing a successful barbeque.

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.

When Anna-Kat brings home a lice infestation, Katie uses it to force bonding time with Taylor. Greg attempts to bond with Oliver (and avoid lice) by camping in the backyard, but Greg becomes concerned when Oliver keeps ditching their campout to be with their new sleazy neighbor named Spencer.

Westport is known for its Halloween tradition of leaving an anonymous note and goodies on a neighbor’s doorstep (called a “Boo”). Katie tries to play it cool but is absolutely giddy when the Ottos receive their first “Boo.”

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.

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.

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; 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 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.

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 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.

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. Her exhaustion leads to a confrontation with the school's overbearing school crossing guard.

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.

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 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'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.

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,

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 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.

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

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 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 Stan, but Katie is less than pleased, especially considering he is married to her nemesis, Chloe Brown Mueller.

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

After Katie encourages Viv to stand up to her husband, she ends up leaving him.

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

Doris insists that Katie attend the charity polo match she's organizing.

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

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.

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

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.