Caitlyn Jenner's Mentor Shares Her Biggest Concern for the Reality TV Star

Season 5 Episode 523
Aired on 04/23/2016 | CC tv-14
While Caitlyn Jenner is a household name, few people know the woman who helped inspire and mentor the reality TV star: author, activist and teacher Jenny Boylan.

Jenny made history when she appeared on The Oprah Winfrey Show in 2003 to discuss her transition from male to female. More recently, Jenny can be found arguing politics with Caitlyn on the E! reality TV show I Am Cait. Jenny says that she was the first transgender person Caitlyn met, and she has continued to be one of Caitlyn's confidants.

Nonetheless, Jenny says on Oprah: Where Are They Now?, she thinks Caitlyn still has much to learn. “She needs to learn about what transgender people’s lives are like, lives of people other than herself,” Jenny says. “One thing about living on top of a mountain in Malibu, it’s kind of a bubble up there.”

While she loves the reality TV star, Jenny says, she’s a little concerned Caitlyn won’t be able to let her hair down. “I’m afraid she lives in a place where she won’t ever be able to celebrate something other than how you look,” Jenny says.