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.
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.
It's Yom Kippur and Jill's parents, Sarah and Alan Kaplan, come 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, Meanwhile, Brooke continues to punish Lex for betraying her.
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.
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."
