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 show up to help celebrate Yom Kippur and to take care of a matter of life and passing.
Fed up with being the last people on Earth not to have seen ''Hamilton'', Jill and Vanessa take part in a desperate quest to get tickets in time for actor 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, 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 and Brad, 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.