Anna-Kat rebels against being Katie's favorite, after she learns how much it annoys her brother and sister. She tails him after one of the calls and finds something entirely different going on. At the end of the episode, Katie goes to confront Spencer about how he may be corrupting Oliver, only to find Spencer dead in his lawn chair. Oliver gets suspended for turning in a store-bought bird feeder for wood shop class, which he fears will now ruin his chances of getting into Harvard. Katie coaxes an upset Taylor until she admits the Blondetourage kicked her out. At the same time, Katie worries about her children becoming too body conscious.
Meanwhile, Katy is hired to plan a party for a Westport businesswomen's association, only to learn it is all her frienemies pretending to be important. 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. But she actually starts to miss her husband when he makes plans with Dane night after night. After discovering that Viv is lying about her husband's affection to keep up appearances, Katie also learns how Viv's first marriage ended and realizes she has to share Greg's interests once in a while. Frustrated with not getting anything on the school's candy-gram day, Anna-Kat scares the other students into giving their candy-grams to her. .
Meanwhile, Anna-Kat worries about whom to sit with at lunch while Franklin is out with the chicken pox. But when she attends a charity polo match at Doris' request, Katie can't help but see that she's started to finally warm up to her surroundings. Katie eventually consoles a tearful Chloe, who claims she has no husband and no friends, and does lock up the venue. Greg and Katie discover that Taylor has two accounts: one that her parents can see, and a second on which she posts racier photos of herself. 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.
Wooten , which is starting to get physical. Oliver steps in with an idea that just might work, but it goes against everything Katie believes. Her attitude changes when a board member reminds Katie she promised to have riding in on an elephant. Anna-Kat's playdate goes off plan but is a success, and Oliver does see Gina but makes the correct decision to stay with his current girlfriend, Brie. Season 3, Episode 18 April 16, 2019 Season 3, Episode 18 April 16, 2019 Katie makes a pact with the girls that she and Taylor can go one day without using their phones in order to avoid buying Anna-Kat a cellphone.
Elsewhere, Greg takes Taylor and Anna-Kat to a Revolutionary War battle reenactment, but Taylor rebels after learning that women are only allowed to be nurses. Ellie, Anna-Kat's special needs teacher, is in danger of being laid off because budget dollars may be reallocated to new parking lot lights. Meanwhile, Taylor starts to get romantic with her classmate and new math tutor, which angers the boy's adoptive mom. 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 worries that both Oliver and Anna-Kat may have learned from her that it's okay to cheat sometimes. 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. Oliver and Cooper attend a party with Gina and Gina's cousin, and both are a little apprehensive when the girls promise a make-out session in a closet.
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. Katie takes refuge at Viv's house, which has backup generators. An attempt to have Anna-Kat butter up Chloe fails, causing Katie to try and get the forceful Angela to help. Meanwhile, Oliver faces competition for Spencer's attention and money when Viv sees the rich old man as a way back to her old social status. Meanwhile, Kathryn is left to manage Anna-Kat's playdate and try to keep Oliver from seeing Gina, who is back and wanting forgiveness after failing in the ballet academy. Created and written by Sarah Dunn and co-executive produced with Aaron Kaplan, Kenny Schwartz, Rick Wiener, and Ruben Fleischer, the Kapital Entertainment— co-production.
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. Meanwhile, Greg and Katie are convinced that Taylor is dating new fling Tripp just to get under their skin, and plot to break up the two. She leaves the kids in the care of Viv, who says she is thinking about having a child and wants to know if she'd make a good mother. Taylor tries to do something about the thin lips she inherited from Grandma Kathryn, Oliver becomes obsessed with developing well-defined calves like the new guy in his ballet class, and Anna-Kat is curious about her teacher's new boob job. Greg thinks recycling would be a great topic, but Oliver turns it around by writing a paper on how recycling is futile because it actually uses more resources than it saves. The day comes for Spencer's lawyer to share his video will.
Season 3, Episode 22 May 14, 2019 Season 3, Episode 22 May 14, 2019 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. Meanwhile, Oliver fears Cooper is ditching him when he sees on social media that Cooper lied about his weekend plans. Meanwhile, Anna-Kat tries to help Trip win back Taylor, and Oliver has a humbling experience during his ballet troupe's holiday performance. It seems she isn't needed when Oliver helps Anna-Kat sell bunches of panda paintings for charity and Greg helps Taylor find a sporting activity she can do while her ankle heals. The result is that Viv leaves Alan and moves in with the Ottos.
Angela succeeds in having sex with a lonely Chloe, but then can't get rid of her. At home, Oliver and Anna-Kat help Greg create a viral message to promote membership in his historical society. Season 3, Episode 8 November 28, 2018 Season 3, Episode 8 November 28, 2018 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. With only the current day to plan, she is able to round up Doris and her husband, Angela and her current girlfriend, and no one else. Anna-Kat will no longer use the restroom at school, Oliver lies about the family's summer vacation in a school presentation, and Taylor is becoming the typical football girlfriend with Trip, making Katie fear she is losing her own identity. Meanwhile, Oliver has to write a persuasive paper for school.
Meanwhile, Anna-Kat takes extreme measures to secure her place as Katie's favorite child. Meanwhile, Greg suspects that Taylor's new musical theater partner, Pierce, is trying to come between her and Trip. Meanwhile, Taylor tricks Oliver into helping her when Luther eats an expensive pair of earrings. Meanwhile, Taylor and Oliver deal with the aftermath of watching a scary movie. At home, Anna-Kat coerces Taylor and Oliver into helping her with a storytelling project. Also, Greg tries to be supportive and accompany his assistant Grant to his first comedy performance, only to find that most of Grant's jokes are at his expense.