When you see Caitlyn Jenner, you're likely to see her in the company of her close friends -- often other strong women in the transgender community. One of those women is professor, author and activist Jenny Boylan, who has become known on "I Am Cait" as Jenner's grounded, straightforward mentor.
Boylan recently opened up to"Oprah: Where Are They Now?"about her friendship with Jenner ,and, particularly, her fears for the reality star. As Boylan says in the above clip, there are good and bad parts of Jenner living out this part of her life so publicly.
"I think that's one of the good things about her show: We're seeing her learning about the community that she is now a part of," Boylan says.
One thing about living on top of a mountain in Malibu, it's kind of a bubble up there.
As we see frequently in "I Am Cait," Boylan in particular has played an important role in helping Jenner learn more about the transgender community. "I became like her transgender Yoda, you know? 'Transgender you are,'" Boylan quips. "I got a chance to be her friend."
However, for all Jenner has learned so far, Boylan says her friend still has a lot further to go.
"She needs to learn about what transgender people's lives are like, lives of people other than herself," Boylan points out. "One thing about living on top of a mountain in Malibu, it's kind of a bubble up there."
Boylan adds that she's also worried about such a bright spotlight impeding Jenner's ability to reach a place where she can uncover her true authenticity.
"I'm just a little concerned for her that she won't ever be able to let her hair down," Boylan says. "And everybody deserves that."
Focusing on what's within can be especially hard in a culture that places so much emphasis on the external.
I'm afraid she lives in a place where she won't ever be able to celebrate something other than how you look.
"Right now, a lot of her life is around being beautiful," Boylan says of Jenner. "She lives in a culture now where there's a lot of hair and makeup and being pretty... And I'm afraid she lives in a place where she won't ever be able to celebrate something other than how you look."
She continues, "Of course we celebrate the way she looks. But there's more to life than what you look like."
It may be a challenge to break from the culture that has become so ingrained among celebrities, but Jenner can do it, her friend believes.
"I trust her," Boylan says. "She'll figure it out."
"Oprah: Where Are They Now?" airs Saturdays at 10 p.m. ET on OWN.
More on WhereAreTheyNow.buzz: Boylan's experience publicly coming out as trans on television in 2003
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