How a Trans Man Helped Me to Better Understand Guys
srsly
this is AI. The real Shiloh was so much cuter <3
From early on, I think girls are given messaging about men that’s kind of confusing.
I can vividly remember being a little girl. I was told by well-intended adults that “men are scary.” To avoid being alone with one. And if a man tried to approach me, to “kick him where it counts!” (that bit of wisdom was imparted by Grandma Foley). I can remember looking at those tall, masculine creatures with eyes of suspicion. At 8 years old, I already thought male teachers and friend’s dads were “sorta creepy.” I think that had to be owed to my conditioning. I couldn’t fully separate them from the images of trench-coats and dark parks that my elders had stamped on my brain.
I think adolescence only added to the confusion. I couldn’t have been older than 10 the first time I heard the expression, “men are pigs who only want one thing.” I’m fairly certain that the statistic about guys thinking about sex every seven seconds was published—monthly—in all my teen mags. I recall shuddering each time I read it. I would survey the peninsula of boys around me in health class, cringing at what must be looping between their temples. But then, you turned the page of the magazine, and there was a cheery quiz about how to tell if your crush liked you. I’m still cringing about the every eight seconds, lady!!
So, as I approached womanhood, I was grossed out by guys, but I was attracted to them. I was having trouble balancing some of the bad outcomes of high testosterone (i.e., sexual assault, rape, cheating on partners, child molestation) with my attraction. How could it be pure with all that contaminating the waters?? I found myself admiring guys from a doorway, but never fully stepping inside.
but then, I met someone who embodied both sexes in one lifetime…
I think my neighborhood (Bushwick in Brooklyn) has probably the highest trans population in America. When I first moved here in 2017, I can’t remember if I had ever spoken to a trans person or not. I had been raised in a queer bubble, where most of the adults at the brunch table were gay, but that was different. All the sudden, I was seeing trans people everywhere. They were rocking skirts, cowgirl boots, and mustaches. They were my clients, introducing themselves at real estate appointments with a demure smile. (“Jaye,” is the most common t-girl name, I find). I met more t-girls than t-guys, but they were there too. The guy I remember most vividly was Shiloh.
Shiloh was a barista at the coffeeshop I used to frequent when I lived on Troutman Street. He was adorable, with bright blue eyes, auburn hair, and a full mustache. He had the nice habit of lighting up when I came to the register, addressing me not by name, but by order: (“Hey! Iced Americano with cream?”). He had fully transitioned. I thought he was just another queer cutie until I noted the trans flag pin on his chest one day.
When I went in around 2 pm, I was guaranteed a seat. One day around 4:30, it was just Shiloh and me. He was closing up, and we got to chatting. He started talking about his past life in Florida, where he had a family who wasn’t supportive of him.
I think non-trans people try to avoid asking invasive questions. I know that it’s still a Brave New World for many. When I was growing up, “gay” was an insult, which meant there was ZERO empathy for the trans experience. The word “tranny” was fodder for Jerry Springer episodes (“MY BOYFRIEND DOESN’T KNOW I’M A MAN!”) or used as a gag in a Rob Schneider movie.
I credit Laverne Cox with turning the game around. Her role as Sophia in Orange is the New Black (2013) was the first sincere depiction of a t-girl that many Americans had seen onscreen (or, period).
I can recall Laverne and fellow t-girl Carmen Carrera being interviewed by Katie Couric around that time. Katie asked if their breasts were real, and if they still had their OPs (original peens). Now, we know in 2025 that that’s a serious breech of etiquette, but in 2013, these two actresses were pioneer women in a lawless land. Laverne and Carmen decided to make this a “teaching moment” by telling Katie that questions like that objectified the trans person (yes!). It kept the focus on their genitals rather than humanity, which was what was really important here (yes yes yes!). I swear, this was a watershed moment, because in one interview, Laverne and Carmen expanded the entire narrative about what a trans person was…and blew it FAR beyond someone else’s LIMITED imagination of them.
I guess Shiloh was my Laverne Cox. He was an open book, and seemed to be receptive to my questions. Those of you who know me know that I’m very curious, asking more questions than the Riddler (I can’t help it, I wanna know!!!)
I didn’t go Katie Couric on him, but I recall that I asked him what the biggest difference between being a woman and a man was. I thought, how special to experience both in one lifetime.
I always wished I could be a man for a week, to experience the secret brotherhood that men had, and to see how women would respond to me. And just to see how it felt. Would I have as many emotions? Would I be as expressive? How would my love of neon colors and leopard print translate?
“Well,” Shiloh laughed, looking sheepish. “The biggest difference is…how horny I am.”
“What??”
“Yeah. All that testosterone makes a big difference. I think about sex all the time now.”
“Wow,” I said. Because truly, I think I had begun to think of male horniness as…a choice, I guess? I thought they acted the way they did to be antagonistic to our lives, in some way. Why the fuck else would a guy say something gross on his Tinder profile like, “I’ll break your heart and your cervix,” or “I’ll make your whole week and your hole weak ;).” Surely it was just to be a troll!
“Do you hate it?” I asked.
“Well, I trust nature,” he replied, quite sagely. “If men have five times the amount of testosterone, there must be a purpose to it. That energy has totally been harnessed in the wrong way, but there’s a point to it, just like there’s a point to all broken systems: law, education, religion, etcetera. But the purpose of male horniness, as I see it, is to perpetuate the species. Every guy who’s ever double-texted you is doing his part to grease the wheels of biology.”
My jaw about hit the floor of the coffeeshop.
“But why don’t guys know better than to not sexualize a NORMAL conversation with a woman? That scares us right the fuck away!”
He pondered this for a moment. Then he once again revealed himself to be the Yoda of Bushwick:
“People have a habit of seeing the world through their own eyes. It reminds me of how my queer male friends always think that straight guys are hitting on them. It’s because they can’t help but see the situation that way. They see them as objects of desire, so they assume to have that mirrored back to them. I think straight men do that with women, unfortunately.”
What he said made total sense. As it turns out, it’s confirmed by science: according to the Economist, “a man’s assessment of how much a woman likes him matches how he feels about her, and is unrelated to how she really feels.” The study concluded,(somewhat wryly) that, “clearly men are prone to wishful thinking.”
I told him I still didn’t understand men being gross on, say, dating apps (see: the “whole week/hole weak” comment, which is actually lifted from real life). Why didn’t they try it once at age 15, realize it didn’t work, and correct their behavior?
“I think it’s the keyboard warrior effect,” he said. “Or the equivalent of trying to throw a basket from half-court when there’s three seconds left on the clock. They do it on the 1% chance the girl will say yes.”
I told Shiloh he was sounding very manly indeed, with his basketball metaphors. Then I remembered a very simple movie quote that I’ve always clung tightly to. It’s from Just One of the Guys, a second tier 80s movie that is exactly what you want it to be. The lead character, Terry feels like she lost the school writing competition because she’s a girl, so she decides to dress in drag and casually enroll at another high school to prove her point. The movie is full of gender-bending yuks and campy cliches that satiate all the sweet spots. It also features an annoying little brother character (Billy? Bobby?) who is the movie’s unexpected Yoda.
Brother Billy/Bobby spends the entire movie trying to lose his virginity. He’s oozing shameless horniness out of his zits. At one point, Terry asks him, “Don’t you have any shame?”
“No, I’m horny,” he answers firmly. “And horniness will overpower shame every single time.”
This quote, and Shiloh, are how I’ve bridged the misunderstanding between that 5x testosterone and me. The guys who say “whole week and “hole weak” are byproducts of a broken system that was intended to serve nature.
But do I understand it??
I think I…do?
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