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 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.

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.

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’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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.