It's Yom Kippur and Jill's parents, Sarah and Alan Kaplan (played by Blythe Danner and Dan Hedaya), come to town to atone, and to take care of a matter of life and death. Vanessa's day is just as serious -- Elliot keeps switching from hot to hideous, and Vanessa flirts with the idea of a breakup at Jill's break-fast. Meanwhile, Brooke continues to punish Lex for betraying her.
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.
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.
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."
At Andy's insistence, Jill reluctantly learns to drive with the help of a dreamy instructor, and then takes her road test with a one-of-a-kind DMV agent, Elna (Amy Sedaris). As Brooke's flagship store opening approaches, she must decide whether or not to invite Lex.
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