Andy makes partner at his firm but feels overshadowed when he learns his brother has just brokered a staggering sale; Jill feels pressured to get her twins into the right kindergarten; Brooke urges Jill to attend a spinning class charity event.
Candace, Brooke and Lex discover they are descended from a Prussian duke named Von Weber, and they want to change their surname; Brooke and Candace take Jill to an exclusive spa to show her the kind of perks that come with being a "Von."
Jill starts stressing over interviews with kindergartens for her twins after she realizes she is the only mom who hasn't heard from any schools yet. Andy tells Jill his mother wants the whole family to attend an interview for a prestigious, invite-only cemetery.
Jill meets a cool mom and thinks she can actually form a friendship with her. She sets up a double date for them and their husbands at a hot Japanese eatery, but the meal leaves a bitter taste when Brooke, Lex and their friends arrive. Meanwhile, Vanessa babysits Jill's children.
Jill takes the subway to Brooklyn with Vanessa to attend their friend's backyard bash, where Jill bonds with the unassuming moms.
Jill must rely on her wits when Brooke goes into labor but cannot make it to her chosen hospital.
Jill reluctantly throws a party for Brooke to introduce her newborn daughter to everyone. Meanwhile, Candace consumes painkillers and cocktails, sending her on a hazy walk on New York's streets; Andy is overwhelmed by the excessive perks of his new job.
Jill becomes overwhelmed with her duties at home, so Brooke convinces her to hire a caretaker. Meanwhile, Jill helps Brooke plan her big benefit party.
Brooke and her mombot posse launch an investigation into who has been telling hard truths about life to their children. Meanwhile, Jill fibs to Vanessa about attending a pricey charity luncheon, and Andy discovers Lex's shocking secret.
Jill is forced to decide between attending Vanessa's 40th birthday party or Brooke's '80s prom-themed gala. Andy throws Jill for a loop when he tells her about Lex's relationship with his assistant. All hell breaks loose at Brooke's event when Candace reveals secrets that shatter the family's seemingly perfect façade.
Jill dips her toe back into the work world by paying a visit to the fashion magazine where she used to work, but she is not opened back with open arms.
Jill's parents come to town to celebrate Yom Kippur and to take care of a matter of life and death.
Jill and Vanessa - tired of being the last people on Earth not to have seen "Hamilton" - go on a desperate quest to get tickets in time for Lin Manuel Miranda's last performance.
At Andy's insistence, Jill reluctantly learns to drive with the help of a cute instructor who isn't as perfect as he appears. As Brooke's flagship store opening approaches, she must decide whether or not to invite Lex.
Miles' behavioral issues cause Jill and Andy to seek advice from a child psychologist (Meredith Vieira), who is eager to shift her focus from Miles to Jill and Andy. Meanwhile, Jill and Vanessa have a friendship crisis over Game of Thrones.
During a historic blizzard, Jill and Andy find the family of their dreams — Meredith (Drew Barrymore) and Brad (John Hodgman), and their three kids — without even leaving their apartment building. Meredith's as irreverent as Jill, Brad's as unpretentious as Andy, and their kids get along like a house on fire. It's a perfect match. Until it's not...
In order to celebrate Brooke and Lex reuniting, Andy and Jill are invited to brunch at Candace's. Andy and Jill are caught up in the doorman strike.
Age issues plague Jill, Andy and Vanessa. Also, Jill and Andy head to a "Dinner in the Dark" with Lex and Brooke.
Things go from great to gruesome when Jill, Andy, and the kids drive to a party in the Hamptons and get stuck in a traffic jam where Jill has a run-in with Brooke's idol, Joy Green, author of The Joy Manifesto. Lex gets an enticing offer for Brooke's company, but Brooke has other ideas.
At Brooke and Lex's vow-renewal ceremony, Jill struggles with telling Brooke that her idol and wedding officiator, Joy Green, is actually a monster.
Jill and Andy are shocked by how much Hazel has matured when they visit her at sleepaway camp, while victims of Ernie Krevitt’s Ponzi scheme struggle with their new financial reality.
Jill comes to her breaking point with Candace living at their apartment and takes surprising action. Vanessa tries to spice up her long-distance relationship with Graham, and Lex receives life-changing news.
Jill flounders to make the right impression at her art show. New York Times best-selling author Derek Blasberg (playing himself) pays a visit to Brooke and Devon at Von Weber headquarters, but things do not go as planned. In a full Lexistential crisis, Lex gets advice from a stranger (Dan Butler).
Jill is forced to face her fear of the suburbs as she attends a traditional Thanksgiving meal with Brooke’s sisters. Upon meeting Barrett (Christine Taylor), a perfectionist homemaker and Berkley (Meredith Hagner), a paragon of condescension, Jill learns why Brooke is the way she is.
Jill is riddled with guilt when Candace makes her dramatic return from sequestration and tells the family the lurid details of the Cruise Ship Murder trial.
Faced with an impossible work deadline on the night of his Dad’s Committee Night Out, Andy takes stimulants. Jill and Vanessa learn the cruel definition of Med Spa as they visit their college friend Ollie at his new venture, Üth.
By day, Jill shoots Brooke’s new line of Von Weber wares, and by night she and Vanessa investigate a rash of infections plaguing the Upper "Yeast" Side. Candace seeks answers for why she keeps getting called "Candy Ass," and Lex tries to make the cut at MarsX.
Jill books a photo shoot in Los Angeles and brings Vanessa along. They follow Dave Navarro (playing himself) on a crazy adventure. Meanwhile, Candace oversteps her boundaries with Hazel, and Lex faces his deepest fears in a zero-gravity chamber.
At the annual family sleepover night at The Brewton Museum of Natural History, animal instinct takes over: Brooke has cold feet about Lex going to Mars, Simone reveals her unexpected true love, Vanessa surprises herself and Andy realizes he’s been chasing the wrong girl all year.
The Weber and von Weber families are thrown into a tizzy when Hazel gets her period . . . but that’s nothing compared with what happens when someone from their past appears on The Wendy Williams Show and spills more tea than the Boston Tea Party.
