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'I Am Cait' Confronts Caitlyn Jenner's Privilege As She Learns What It's Really Like To Be Trans In America

As it turns out, Jenner doesn't have it all figured out quite yet.

The premiere episode of "I Am Cait" introduced us to Caitlyn Jenner -- her world, her family and her new life as an advocate for the transgender community. But tonight's second episode dug even deeper and underlined how privileged and "singular" Caitlyn's trans experience really is.

For example, Caitlyn is shocked to learn how many young transgender people turn to sex work to survive --- and how hard it can be for a trans person to obtain hormone treatments.

When confronted with the harrowing true-life stories of other trans women, Caitlyn's privilege and conservative views were put under the microscope. As it turns out, Caitlyn doesn't have things all figured out, after all. Here are the highlights from this week's episode of "I Am Cait," in which Caitlyn learns that being a transgender spokeswoman is more than hair and makeup:

  1. Caitlyn struggles to find her voice.
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    As cool and confident as Caitlyn may appear, she's still struggling with her femininity. For Cait, one quote (via transgender author Jenny Boylan) sums it all up: "I never felt feminine but I always felt female."

    One of Caitlyn's biggest insecurities is her voice. "Your voice can out you anytime," she says during the opening minutes of the episode. While she's managed to get the fashion and beauty thing down -- with the help of her stepdaughter Kim Kardashian -- she admits that her voice "is certainly not quite right."

    Now, what's "right" is subjective to Caitlyn and what she wants. So Kim encourages her to "try out" some voices. With a little help from Kardashian BFF Malika Haqq, Caitlyn tries out some feminine voices, but none of them really do it for Kim, who is Caitlyn's go-to authority for "feminine tips." But when Caitlyn mentions the possibility of vocal chord surgery, Kim doesn't think she should take the risk.

  2. "I'm free, baby!"

    Every girl needs her squad, and Caitlyn's is totally FOMO-inducing. She's assembled a squad of incredible trans women -- which included Candis Cayne, Chandi Moore, Drian Juarez and Jenny Boylan -- for a sophisticated girls night.

    They all admit to having mixed feelings over Caitlyn's Vanity Fair article. On one hand, it was a monumental moment for the trans community. But on the other, it only further segregated Caitlyn from the community she now finds herself a spokesperson of. So Caitlyn has the awesome idea to go on a road trip to San Francisco -- her first time out of the comfort of Malibu since coming out as Caitlyn.

    While they're in San Fran, trans activist Jen Richards suggests that they stop at the local HRC (Human Rights Campaign) so that Caitlyn can hear from real trans women about their experiences. And thus Caitlyn's Great Escape is conceived. The girls literally need to sneak Caitlyn out of the Los Angeles area in a bus to avoid the paparazzi.

  3. Caitlyn's bathing suit blues.
    Annie Liebovitz/ Vanity Fair

    When all of the girls hit the hot tub in their bathing suits, Caitlyn decides she doesn't feel ready to "expose" herself in her designer swimsuit just yet. Caitlyn hasn't worn a swimsuit in public yet, so it's a personal decision for her -- one that is nobody's business but her own. She's only been out for two weeks at this point, and we totally respect her decision.

  4. Caitlyn gets a reality check.

    This episode confronted Caitlyn's conservative, and somewhat privileged, views of the world with the experience of real-life trans people.

    It all gets kinda awkward when the girls educate Caitlyn on the big issues transgender people face on the daily. "They’re homeless, unemployed, so it's just going to take a lot more," Moore says. Richards adds that entry-level jobs may be a solution to this problem -- but Caitlyn disagrees, instead bringing up something more political.

    "Can't they make more not working with social programs than they actually can with an entry-level job?" Jenner asks. "... You don't want people to get totally dependent on it. That's when they get in trouble. 'Why should I work?'"

    Being a conservative woman, Caitlyn is no fan of government-funded social programs, which alarms her new girlfriends. How is Jenner supposed to speak for the trans community when she doesn't even know the extent of the horrible violence and prejudice trans people face? (Honestly, we're so glad "I Am Cait" isn't afraid to have these conversations.)

    "Caitlyn has every right to be just as conservative as she choses, but many transgender men and women need social programs to survive, and that's nothing to be ashamed of," Boylan says. "Living in the bubble is an impediment to understanding other people. Cait's going to be a spokesperson for the community. This is something she's going to have to understand."

    The tense final moments of the episode saw her in the middle of a heated discussion with transgender women at the San Francisco's Human Rights Campaign office, many of whom questioned whether she should be the face of the transgender community at all.

    For Caitlyn and us, "I Am Cait" is proving to be an important learning lesson.