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.

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.

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.

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 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.

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.

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.

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

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 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.

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.

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.

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.

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.

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.”

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.

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 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 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.

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.

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.

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.

After the passing of a family friend, the Ottos all react differently to the allotment of the deceased's inheritance.

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.