In the series premiere, Caitlyn Jenner proudly announces her true self to the world via Vanity Fair, but still struggles with meeting some of her family for the first time. Meanwhile, Caitlyn is also inspired to learn more about transgender youth in crisis.

Cait is elated to be on a road trip with a group of her new transgender friends, but they question if her privileged status stops her from becoming their new spokesperson.

Cait wants to give her new friends the trip of a lifetime and they challenge her to break down her walls and get personal; Cait must find a way 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 refers to the LGBT community as "they" until she visits a NYC Pride event and finally feels included; Caitlyn tries to reconnect with her male friends and Scott Disick offers his advice.

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; Jenny Boylan urges Cait to talk about who she's attracted to.