Jill dips her toe back in the work world by visiting the fashion magazine where she used to work. But her excitement at being welcomed back with open arms is short-lived.

It's Yom Kippur and Jill's parents come to town - to atone, 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.

Jill is pushed to get a drivers license. Brooke celebrates the opening of her store.

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...

A doorman strike turns the Upper East Side into a warzone. During a Valentine's Day dinner at Candace's, Jill joins the picket line and Andy inadvertently becomes a scab, while Lex and Brooke take a big step in their relationship.

Jill, Andy, and Vanessa all individually struggle with getting older. Lex and Brooke take Jill and Andy out for an enlightening Dinner in the Dark.

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 (Molly Ringwald), 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 (Molly Ringwald), is actually a monster.