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.

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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.

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On Katie's day off, Kathryn drops by and drives a wedge between mother and daughters. Meanwhile, Katie could be the cause of Oliver's suspension from school.

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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.

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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.

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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. 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. Over time, Katie realizes how judgmental she has become and that she is part of the ...

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Katie is upset to discover that the Ottos' pin-code spells out Greg's ex's name; the kids experience trouble in their love lives.

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Katie convinces a hot young trophy wife to volunteer as room mom for Anna-Kat's class; Greg enlists the help of the kids to get Katie's mom to take an interest in someone other than herself.

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Katie begins to miss the spontaneity and unpredictability of being young and in love; Kathryn's plan to soothe Oliver's heartbreak backfires when she tracks down an old boyfriend and he is not as she remembers.

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Katie strives to keep her long-separated parents apart when her father arrives in time to surprise the family for Christmas; Anna-Kat tries to help Trip win Taylor back.

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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.

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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.

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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.

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Katie panics when Greg is hit with a bout of baby fever; Taylor tricks Oliver into helping her when Luther eats an expensive pair of earrings.

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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."

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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.

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When Katie forgets Greg's birthday, she attempts to make up for it by pulling together a last-minute dinner party.

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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.

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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.

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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.

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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.

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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.

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Frustrated by the lack of appreciation for all she does, Katie decides to leave the family to fend for itself.

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