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 ends up realizing just how hard it can be to date a trans woman after hearing Candis talk.

Cait does not want to use her new name at her country club until she discusses the matter with Candis.