Maura moves out of the family house and into a lively new apartment complex, just as Sarah needs a new home after dismantling her perfect life. Josh has to reconsider his sudden vision of starting a family, while Ali finds some new boundaries to cross.

Maura finally comes out to Ali, and they join Sarah on a field trip to the mall - where they all get rude lessons in womanhood. Josh is forced to confront his past thanks to questions from Syd (Carrie Brownstein) about his longtime relationship with Rita.

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.