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When Shelly's husband Ed goes missing, Sarah, Josh and Ali set out to find him, and instead find themselves lost in their past. Ali can no longer keep Maura's secret from Josh, which sends him into a tailspin. When Maura runs into a Pfefferman family friend she takes a stand for her new identity.

As they struggle to come to terms with Maura, Josh looks for answers from a rabbi named Raquel (Kathryn Hahn), and Ali looks for answers in a Gender Studies class with Syd. Sarah is left to answer questions from her own kids, who meet Maura for the first time.

Josh goes on a date with Rabbi Raquel while Ali explores her feminine side with a TA from Gender Studies class. The kids turn out for Maura's performance in a talent show, but her delight quickly turns to dejection.

In a flashback, Mort escapes with friend Mark (Bradley Whitford) to a cross-dressing retreat in the woods, and becomes captivated with a very accepting woman named Connie (Michaela Watkins). Left alone after cancelling her Bat Mitzvah, 13-year-old Ali finds trouble with an older man at the beach.

Maura finds solace with ex-wife Shelly, and the two hatch a plot to help Ed realize his wishes. Sarah spends time with her ex-husband and begins to question their breakup, while Raquel finally breaks through to Josh. And when the entire family is summoned to Shelly's, they are in for a few surprises.

A funeral brings all the Pfeffermans together and reunites them with their past - Shelley and Maura with old friends, Sarah with her ex, and Josh with his teenage babysitter - who brings a 17-year-old boy. Just when they thought there were no more secrets, the family busts out a few more.