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.

Sarah and Tammy are getting married, while Maura and Ali are visited by ghosts from the past and Josh and Rabbi Raquel can't hide their big news.

Josh's bonding with Colton comes at a price; Sarah feels more like an outsider than ever following a disastrous school gala; a visit to Grandma Rose leaves Ali and Syd with questions; Maura searches for autonomy.

Maura learns more about the trans experience; Josh heads down a reckless path; Ali and Sarah take Maura to the Idyllwild Wimmin's Music Festival.

Maura makes a new friend and has a rude awakening at the music festival; Sarah experiences liberation from an unlikely source; Ali makes an unexpected journey to the past.