The road trip continues as Caitlyn's new friends help her wrestle with the many, many layers of her new life.

By Melissa Maerz
August 10, 2015 at 02:48 PM EDT
E! Entertainment
S1 E3
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How is it possible to finally reveal who you’ve always been inside, ever since you were born, and also become someone brand new, with a new name and a new look and maybe even a whole new life?

It’s a question that many transgender people face, though it’s hard to imagine anyone feeling that double consciousness more acutely than Caitlyn Jenner. She has arguably made the most public transition in American history. Her greatest fear, she says, is “exposing [myself] to the world, and doing it live” at the ESPYs. Some people might say that it’s her responsibility, as the de facto spokeswoman for transgender women, to leave “Bruce” behind and show the world that Caitlyn has always been her only “true self.” But it’s refreshing to see I Am Cait acknowledge that transitions are never that simple. Caitlyn still refers to herself as her children’s “daddy.” Sometimes, she can’t quite figure out how to reconcile the conservative politics that defined her before with the progressive politics that she’s learning to love as a result of joining the transgender community. As her new friend Candis Cayne points out, that’s okay. “You were this other person,” Candis says. “And you’re allowed to be both.”

This week’s episode begins with a good lesson from Caitlyn in How to Be Both. We begin where we left off last week, in the midst of an intense conversation at the Human Rights Campaign about the struggles many transgender women face. It’s an incredibly sad conversation. One transgender woman confesses that she was forced into sex work and stabbed by a client. A soft-spoken transgender woman named Blossom says she worked hard to get straight-As and still couldn’t get into nursing school, simply because of who she is. She mentions that Ellen Degeneres is her hero, for being brave enough to come out as a lesbian so long ago, and Blossom hopes that one day being transgender will be as uncontroversial as being gay. By the end of her speech, many people listening are crying. (No, I wasn’t crying. YOU were crying. Shut up! Sniff!)

At first, it sounds like Caitlyn totally missed the point of the whole conversation. After her friend Jen Richards mentions that it’s much harder for Blossom, as a black transgender woman, to do everything she wants to do, Caitlyn says that, for her, the biggest problem has been dealing with the paparazzi. Maybe she’s just trying to put things in perspective, but watching this, you kind of want to pat-pat Caitlyn’s billion-dollar hairdo and whisper, Oh, honey, you do know that you shouldn’t compare the insurmountable prejudice Blossom is facing with the struggles of the rich and famous, right? And yet, just as you’re losing hope in Caitlyn, she calls her producer into the room, asking her to submit the footage of Blossom’s story to Ellen Degeneres and urge her to air it on her show, so that Caitlyn can help Blossom go to nursing school. Now, everyone’s crying. Yes, Caitlyn is still basically a Kardashian, way too obsessed with her hair and makeup. But she’s also an important activist. She’s allowed to be both.

Fittingly, this show is a lesson in How to Be Both, too. It’s a fizzy reality TV show like Keeping Up with the Kardashians, and it’s also a serious spin-off that feels like a totally different show. We get to see the ladies vamping it up at a roller-skating rink. (Check out Caitlyn’s junior-high-school-girl innocence in her knee-high socks and flower-print skirt!) They go motocross biking, and Candis whips her long blonde hair out of her helmet, heavy-metal-video-style. They drink wine, discuss bra strap etiquette, and model bathing suits for one another. Caitlyn opts for a conservative white one that’s not quite as “revealing in the cleavage department” as the sexy one-piece Kim Kardashian bought her. Yes, the moment when Caitlyn finally puts on a bathing suit is inherently political: it’s her first time doing this in public as a transgender woman. But in other ways, it’s totally mundane. She’s worried about how she looks in a bathing suit? Welcome to what it’s like to be a woman, whether you’re transgender or not.

Then again, maybe I shouldn’t say that. This week’s episode emphasizes that gender can’t be so easily defined. Caitlyn is the girliest of women, and yet she still loves riding motocross bikes, a sport that’s traditionally beloved by men. Later, we’re reminded that gender and sexuality are two totally different things. Jenny Boylan, who’s in a relationship with a woman, proves that just because you’re a transgender woman doesn’t necessarily mean you’re interested in dating men. There’s a great discussion between Caitlyn and her friends about whether transgender women can date other women. “You would feel much more feminine with a guy,” Caitlyn says, as if two feminine women couldn’t date each other. Ugh.

It’s clear that she’s still wrestling with societal standards of what a woman should be. If she were to date a man, she says, “I would want to have the right parts…” A friend corrects her. “The parts YOU feel comfortable with,” she says.

Caitlyn’s still deciding if she’s open to dating men, but in the meantime, her friend Chandi Moore offers the best words of wisdom about love. “Gender is more than just male to female,” Chandi says. “I want someone who is a great all around person… if you like Beyoncé, that’s a bonus.” Someone needs to bedazzle that message in sequins on Chandi’s shirt.

During the final night of the ladies’ road trip, everyone gets choked up again, this time while talking about the women who’ve inspired them over the years. Caitlyn toasts the whole table. “What has really impressed me is, at this point in their lives, how normal these girls are,” she says.

She’s so enamored with her new friends, she’s forgetting the old ones, particularly her assistant, Ronda, who’s been there for her through everything. Ronda has already told Jenny how hurtful it is to see Caitlyn ignore her in favor of this new group, and Jenny points out that many transgender women go through a phase where they’re high on a happy “pink cloud” and get overly self-involved. “Have you ever heard of bridezilla?” she asks. “Well, there is something called transzilla.” By the end of the episode, Caitlyn and Ronda have made up, and no doubt E! has optioned a new reality show called Transzillas.

Will we keep floating on this same pink cloud next week? At one point, Caitlyn demands that she only hear happy stories from here on out. “If I hear anyone crying,” she says, “you’re gonna lose your dessert!” But the teaser shot of Kim and Khloe Kardashian arguing over Caitlyn’s Vanity Fair cover story suggests that everyone’s getting their Pinkberry privileges revoked next week. So let’s keep this warm-fuzzy feeling while we can, shall we? For now, I just want to say: Blossom, once you get out of school, you can be my nurse any time.

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