Caitlyn Jenner proudly announces her true self to the world via a Vanity Fair magazine cover story, but at the same time struggles with meeting some of her family for the first time. Meanwhile, she becomes inspired to learn more about transgender youth in crisis.
Cait is pleased to be on a road trip with her new transgender friends, but they question if her privileged status is going to stop her from being their new spokesperson.
Cait sets out to give her new friends the trip of a lifetime, and in turn, they challenge Cait to break down her walls and get personal. Meanwhile, Cait must figure out how to balance her old friendships with her new ones.
Candis invites Cait over for an all-girl sleep over; Kim and Khloe discuss comments aimed at Cait's ex, their mother, in her Vanity Fair article; later, Cait visits a support group for families with children that are transitioning.
Caitlyn begins to feel included in the LGBT community after attending a New York City Pride event; at the same time, she struggles to reconnect with her male friends; and receives advice from Scott Disick.
Cait realizes how hard it can be to date as a trans woman when Candis talks about her relationship history; Cait tries to get Candis to believe in love again, while Jenny Boylan urges Cait to talk about who she's attracted to.
Cait is hesitant to use her new name at her country club, but she officially changes her IDs when Candis calls her out for playing both sides; Cait's anxiety grows as she prepares for The ESPYs and a sit-down with Kris Jenner.
Cait and Kris Jenner sit-down to air their grievances with each other in an attempt to move forward as a family; Cait plans a spiritual ceremony to claim her new name, and it becomes a symbolic celebration for her new friends also.
Cait and her friends start a cross-country road trip in a tour bus, and the other women corner Cait about her sexual orientation and her politics.
After a heated political argument on the bus, the women decide to confront Cait on her aggressive debating style and suggest a more feminine approach.
Cait reveals her deepest fears about dating men after she witnesses Candis get stood up by a guy because she's trans.
After Cait is challenged to control herself during the Democratic debates, the women are challenged by a visit to Cait's alma mater, a conservative, Christian college in Iowa.
When the newly sober Scott visits Cait on the road trip, they struggle to find common ground. Meanwhile, Cait and the women attend a ceremony for Transgender Day of Remembrance.
Kris visits Cait in New Orleans, to try improve their relationship, but when old wounds arise between the exes, Cait's friends must intervene.
Cait's personal growth on the road trip is tested when she tries to apologize to her ex-wife Kris for her part in the ending of their marriage; Candis looks into her options to adopt a baby.
Caitlyn, bent on proving her commitment to the LGBT cause, risks arrest in Houston with her friends; Ella tries to mend fences with her father, who struggles to accept her transition.
