Maura embraces her new journey, but nothing about life as a woman is easy -- making friends, finding a new community, and above all, coming out to her children. Sarah introduces her husband (Rob Huebel) to her ex-girlfriend Tammy (Melora Hardin). Josh pays a visit to his ex-babysitter Rita, as Ali gets closer to her trainer.
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.
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 canceling 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.
Josh has a pool party for his new band, but he and his siblings are caught off-guard when Maura and Shelly arrive together; Ali reconnects with an old friend; Sarah finds her past catching up with her.
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.
Ali finds herself a little too close to Leslie when she seeks Leslie's advice on her UCLA application; Josh confronts Shelly about the past; Sarah uses a hard-won date night to explore some of her sexual fantasies.
While working at an LGBT suicide hotline, Maura receives a distressing call from a young trans woman, Elizah. Afraid that Elizah will hurt herself, Maura goes on an odyssey through South Central LA to find the troubled teen and lands herself in the hospital.
After a health scare, Maura confronts death and her relationship to her body. Sarah hopes to join the MidCity Temple board. Shelly plans a one woman show with Buzzy. Dissatisfied with their lives, Josh and Ali play married couple.
Relationships are tested as the Pfefferman family gather for Maura's birthday. Sarah confronts Buzzy on temple board politics and Maura makes a big announcement, experiencing pushback from both Vicki and Shelly. The night culminates in a game of Sardines, forcing tense situations into tight spaces.
Maura gets an exciting peek at the future with a visit to the plastic surgeon's office but fails to muster the same enthusiasm from Vicki on a fun night out. Josh visits an unusually upbeat Rita while Ali and Leslie struggle with intimacy. Sarah finds distraction from her personal troubles by spearheading an unorthodox approach to Judaism.
The Pfefferman family gathers at Hineni to support Sarah's alternative spiritual endeavor. After the news of a close friend's untimely passing, a distressed Josh leans on Raquel for support. Ali ends the night by witnessing the pitfalls of Leslie's prejudices.
Josh hits the road with an unlikely copilot, stirring up some undeniable chemistry along the way. Back at home, Shelly becomes wary of Buzzy's outlandish spending while Ali sees God during a nitrous induced trip at the dentist's office.
Josh arrives in Overland Park and delivers difficult news to Colton. Sarah oversteps her boundaries with Raquel, putting the Hineni Seder in danger. A tough conversation with Bryna brings up some big issues between Maura and Vicki.
Boyle Heights, 1958. 12 year old Maura's femininity causes a clash between her mother Rose and her grandparents, Haim and Yetta. Across town, 12 year old Shelly quits the school play and stops eating but won't tell anyone why. Flash forward to 1966, where 21 year olds Mort and Shelly carry on a secret affair.
After reconnecting with Colton, Josh decides to move to Overland Park, until a concerned Ali travels to him, intending to bring him home. Feeling abandoned, Sarah has trouble controlling her rage. Shelly confronts Buzzy about his spending, leading to some unforeseen revelations. Newly single Maura has an exciting, surprising night out.
The Pfeffermans escape their problems on land by taking a cruise together. Though the clan spends most of the cruise apart - venturing on their own journeys of self discovery - they ultimately find themselves coming together at the Seder that almost wasn't.
An exciting offer draws Maura to Tel Aviv. Hoping for a fresh start, Shelly sells her condo and shacks up with Josh. Grappling with their family's weird intimacy issues, Sarah, Ali, and Josh attend a sex and love addicts meeting together. Ali rents out the Pfefferman house and contends with weird AirBnBers.
Ali is blindsided when Leslie goes public with the details of their relationship. Sarah is ignited by a new connection with her daughter's former teacher, Lila. Josh unexpectedly encounters an ex. Shelly takes up improv. Ali joins Maura on her trip to Israel and their journey gets off to a bumpy start.
Sarah tests a new parenting style and is shocked to discover that it works. Josh reconnects with Dr. Steve as tensions rise at home with Shelly. Drawn in by an intriguing new friend, Ali travels to Palestine. Maura makes a life-changing discovery about her family history.
Sarah and Len divert a family outing to visit Lila's mom, leading to a blowup between the siblings. Ali breaks off from the group to visit her friend Lyfe in Ramallah while the other Pfeffermans engage in some questionably authentic tourism of desert life.
Feeling compelled to learn more about herself in Israel, Ali stays back as the rest of the family returns to Los Angeles. Sarah, Len, and Lila reevaluate their complicated relationship. Josh confronts his sex and love issues head on. Maura and Davina reclaim the Pfefferman house from an unwanted guest.