Jenny Boylan Tells Caitlyn Jenner: 'Don't Be a Stupid' Woman

"We live in a world that has no place for us," Zackary Drucker told Caitlyn Jenner and friends as they traded dating nightmare tales. This week's I Am Cait focused on love: finding it, losing it, keeping it and being honest with ourselves about it. And Cait got called on the carpet by the indomitable Jennifer Finney Boylan.

Every week, The Advocate is presenting a look at the moments in each episode that we feel resonate most strongly within the trans community, through two perspectives. What you'll read here are just opinions, not facts.

I'm news editor Dawn Ennis, writing from my experience as a woman assigned male at birth who transitioned in the public eye. To provide variety, a different individual is joining me each week on what we're calling "The Advocate's sofa," comparing our notes as we watch, for the duration of the season.

This week I'm joined by trans man Gunner Scott of Seattle. Scott is director of programs at the Pride Foundation, who "eats fire for social justice, DJs lefty dance parties, and thinks way too much about politics." And on his website he describes himself as an activist, photographer, artist, traveler, and reluctant writer.

Gunner Scott: I felt so uncomfortable for Cait as she discussed dating with Jenny. A conversation about fear and it was so public.

Dawn Ennis: Well, full disclosure to our readers, you and I are both Facebook friends with Boylan. And she told me this confrontation about sexuality was the moment in the whole series of which she was most proud: a crash course, if you will, in feminism.

"Caitlyn Jenner you're pulling back on me," Boylan said. She compared how Jenner avoided the gender question all her adult life, first with the Olympics and then over and over with her families: "You're running away."

And then Cait stepped in it for realz, telling JFB, "I want to be a 'normal' woman," and talking about how a man treats her makes her feel more feminine. To me, Jenny was right on target, saying, "You don't need a man to make you a woman." I'll admit, I was cheering! And Boylan's other zinger was: "You went to so much trouble to be a woman. Don't be a stupid one." That was hardcore, Jenny, and you know what? I'm proud of you. But Gunner, why did that scene make you feel uncomfortable?

Scott: Topics like dating and love after transitioning typically take place in the safety of a support group, with close friends, and for some with a therapist.

Ennis: Point taken, but nothing about what's happened to Cait, even before she came out, is "typical." She told Boylan, "I'll play that card someday," excusing herself from facing he own sexuality because she is "focused on educating people."

Scott: I found it interesting that Cait is "obsessed" with educating people about transgender people and experiences, like none of us have been doing that for years, even before she won her Olympic Gold medal or Stonewall happened.

I think she should spend some time with some grassroots activists, outside California, and learning some transgender history.

Ennis: Absolutely. What we've seen her do so far is chat with HRC and Kate Borstein, but more would be better. And she needs to be educated before she can educate. What do you recommend?

Scott: I would suggest she read Transgender History (Seal Studies) by Susan Stryker, Stonewall by Martin Duberman, and Nobody Passes: Rejecting the Rules of Gender and Conformity by Mattilda Bernstein Sycamore.

Ennis: What did you think about that dinner with Zackary Drucker, Jen Richards, Chandi Moore, Candis Cayne, and other trans women -- oh, and wouldn't it be nice if we all had our own private chef to cook for us?!?

Scott: Watching Cait interact with the world is surreal, from the dinner scene, to visiting the camp for transgender youth. The reality that 99.9 percent of transgender people's experience is NOT what Cait is experiencing by virtue of her privilege and wealth. She can be in the L.A. bubble.

Ennis: Well, Jenner looked pained to be outside her comfort zone at the Abbey, as hunky men cavorted in tiny bikini briefs. I've been there, had fun, and it looked like nothing short of torture for Cait. I wouldn't mind seeing more of that, and hearing more trans dating horror stories.

Scott: The dinner scene seemed contrived, but the honesty of Zackary talking about how the world sees transgender people: "the world has no place for transgender people." And Cait's reaction to that revelation was one of the most authentic and real moments on the show, which otherwise feels like the "Real Housewives" without all the yelling and screaming.

Ennis: What about that statment one woman made about trans men? That you don't "come with the shame that a cis male comes with."

Scott: I found the dinner conversation of suggesting Cait date a trans man funny and uncomfortable, as though we are a better alternative to cis men, which feels like they could have just said "real men" in place of cis, because contrary to the conversation, some transgender men do bring the same baggage as cisgender men to relationships ... and then again, some of us are gay! As Jenny noted in the earlier scene to Cait, that she is a real woman, so are trans men real men.

Ennis: I was moved as Candis talked about her lonely life in L.A. She's clearly reaching out to Cait for more than friendship. Not sure if Cait is seeing what we are seeing!

Scott: I found the scenes between Cait and Candis really sweet and and I think I would enjoy the show much more if the focus on was on their relationship and how it evolves and less of the contrived scenes. The energy between Cait and Candis is real, and it comes through.

Ennis: But so is the sorrow she feels, over what she described as "failed relationship after failed relationship." She confessed to Cait, "I allowed men to treat me the way no woman should be treated."

Scott: While the conversation about the domestic violence Candis experienced was heartbreaking, that was one of the most educational moments of the show: her description of how hard it is to leave is reality for too many transgender women and transgender men. Cait's reaction and her desire to give Candis hope and positivity was lovely to watch.

This episode gave visibility to an important issue: there is no language to positively describe those who are attracted to transgender people, and that the labels of sexual orientation currently do not capture that. There are also so few positive portrayals of happy and healthy couples where one or both are transgender people. The stigma of homophobia and transphobia is so deep that it stops love for so many of us.

Ennis: Another truly educational moment was when Cait and Jen Richards took Candis to a camp for trans chldren! Those kids were so honest, so strong, and heartwarming!

Scott: I appreciated the transgender youth speaking about their experiences and being able to see the great work Camp Aranu'tiq does for transgender teens and their families. But the episode made it seem like a stop-by for Cait and Candis. I hope that the youth got something out of the visit.

Ennis: What did you think when Jenner freaked out about having the matchmaker find her a date? And what was that tripe about how men think versus how women respond to his survey?

Scott: The dating coach... ugh. Really? Saying someone answers a question a certain way means they have masculine thinking ... because they think like an engineer? There are plenty of women who are engineers! I mean, really, can we just quit with the sexism and traditional gender roles?

Ennis: Yes, I thought that same thing when Cait pumped her gas, made a fuss about holding open the door for Candis, and took her car to a mechanic, as if she couldn't figure out how to do that herself? "You need someone in your life to take care of things," she said. Ugh, so chauvinist, was my first thought. But when I thought about, I realized it's really not that surprising a reaction, given that she is still learning who she is, and all those things Jenny Boylan tried to explain about being a woman and finding her place in our world.

Scott: The closing scenes with all the cars parked in Cait's driveway and the reality of her privilege and wealth just highlights for me the lack of resources the overall transgender movement has.

Ennis: And to top everything, then she rents Candis a Lamborghini! This week's second example of how her life is just soooo different from everyone else. Not just trans people, everyone. But, if we're being honest, who wouldn't like to be rich?

Scott: I hope at some point, if Cait really wants to educate people about the issues we face, she spends some time with grassroots transgender activists that are invisible to the larger public, but spend their lives trying to make the world a just and civil place for transgender people, particularly those facing violence, poverty, homelessness, and discrimination.

Ennis: I hope so too. At least she ended on a positive note, saying she doesn't know what the future holds: "I won't say no to anything." Thank you, Gunner, for joining me on The Advocate's sofa!

Next week, Kris Jenner meets her ex-husband, Cait!

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Watch the clip below in which Jenner gets called out by Jenny Boylan, from E!'s I Am Cait: