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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.
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.
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.