Episode 1
Cait and her friends embark on an epic cross-country road trip in a tour bus, and the other women take the opportunity to corner Cait about her sexual orientation and her politics.
Episode 2
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.
Episode 3
Cait reveals her deepest fears about dating men after she witnesses Candis get stood up by a guy because she's trans.
Episode 4
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.
Episode 5
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.
Episode 6
In an attempt to improve their relationship, Kris visits Cait in New Orleans, but when old wounds arise between the exes, Cait's friends must intervene.
Episode 7
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.
Episode 8
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.
