Dating (or usually not) as trans & Two Spirit

(Photo: Adrian Jawort)

Although some trans women are very self-critical, most aren't shallow since so many have been looked down upon by society after coming out. Reading social media comment sections on articles about trans people is self-mortification they are so mocked and dehumanized, so they never want others to feel that ugliness. says Adrian Jawort

A humble, handsome, and humorous gentleman contacted me via a transgender dating site. After several cordial conversations that grew beyond pleasantries, they began to be drawn to me beyond looks via the way I talked/typed, how I reacted without judgment and consideration to their questions, my sardonic wit, and how deeply passionate I was about art.

After a couple more weeks of conversations, he wanted to travel to Montana to meet me in person. With a layover, it would take the same amount of time to fly to my town as it would be to drive. He debated the logistics, saying, “seven hours to drive, seven hours to fly. Ain’t Billings, Montana a geographic oddity!”

I laughed at the Oh Brother Where Art Thou reference. However, when he said he hoped we could form a serious relationship, I felt bad telling them although I'm pansexual, I wasn’t considering a long-term relationship with a male at this point as I still lean towards women for that. Despite the setback, we remained online friends since we’d shared so many honest conversations regarding our failed relationships, my being trans and a Northern Cheyenne Two Spirit in a red state conservative area, and recovery from addiction.

Luckily for this bachelor, another trans woman eventually agreed to meet him, and my god she was beautiful – and well-educated to boot. Leery of scammers via fake profiles, he was initially suspicious of her intentions until he confirmed her as legit and she’d even buy her own plane ticket to visit him as her job had her traveling a lot anyway. Then he became worried he’d disappoint her. "Why would she like me? I am almost 15 years older than her!" He is like 50, and she is about 35.

By then, she’d no doubt gotten to know him as I legit, down to earth man who went through a messy divorce they’re finally getting over. He’s got a hole in his soul he wants filled; and has a passionate heart he’s eager to share a life with. He asked for advice on how to approach this other trans woman to prove their sincerity. I told them like any single person, know we trans women oft feel alone, but also with the added ‘bonuses’ of former friends and families who've pushed us away. But relationship-wise, we feel even further ostracized because we’re usually seen as taboo societal-wise, an odd curiosity, or as a fetish of ‘trans chasers’—or men who view us as mere sexualized objects. (A catch-22 for men who legit admire trans women is they’re thrown in with "chasers.") Knowing this with a heart toward empathy carries a lot of weight, I said, as does validation and respecting her womanhood by not treating her as awkwardly “other.”

When fully en femme, I’m a reasonably attractive woman if I must humble brag, and it’d be ultra-easy for me get casual hookups despite living in an area that voted nearly two-thirds for Trump. And although I don’t shame people’s natural sexual drives, it’s worth noting the hypocrisy of conservative states with anti-transgender laws have paradoxically high rates of trans porn consumption. In North Carolina with their infamous anti-LGBTQ “bathroom bill,” for instance, the bestselling porn titles are transwomen-based. Conservative-minded people may masturbate to trans women, then with that same hand vote against their Constitutional rights as people in the voting booth.

"Flattering" as it may be to be seen as a desirous sexually (my messages on dating and hookup sites are crazy with lewdness), that fetish perception would undoubtedly get old when one is striving for a healthy, committed relationship, especially as I notice a lot of us in the trans community are artsy empaths who really crave that sensitive "soul to soul" connection as pesky humans are wont to do. Anyway, the gentleman said of his new crush, "I honestly don't think she realizes how beautiful she is."

I explained, "Trust me, if her inbox is anything like mine, it has tons of messages from trans chasers telling her how hot she is. But … when you tell her she’s beautiful, she knows you mean it.”

Although this trans woman is “passable” — as in not distinguishable from a cisgender/biological woman — with a great body, some trans women become highly critical of their own faces and bodies as not femme enough. And such becomes their quest to “pass” as biological female for various reasons from yearning for their outside to look as they feel on the inside, or perhaps basic safety reasons like not wanting to be “clocked” (discovered) as trans to be discriminated or possibly attacked for it. While many trans women are wholly content in their bodies, for a lot of us — and I feel this too as an 6 foot tall Amazonian trans/Two Spirit who collects second looks — there’s a deeply ingrained, very self-conscious, self-critique-dysphoria you’re always working on trying to assuage that fuels constant efforts to pass. For better or worse, it’s what pushes me to run that extra three miles in an effort to trim my “mannish” body after running, do hormone replacement therapy, or spend an extra half hour carefully applying makeup just to go to the grocery store. Even if I ever got to that coveted “passing” stage, would I do personally facial feminization or liposuction surgery if I could afford it? Yeah. Maybe. Prolly. Still, most people chasing the fountain of youth and getting cosmetic surgeries aren’t trans, it must be noted.

Although some of us trans women are very self-critical, most of us aren't shallow since so many of us have been looked down upon by society after coming out. Reading social media comment sections on articles about trans people is self-mortification we’re so mocked and dehumanized, so we never want others to feel that ugliness.

I go to a transgender support group and I noticed for those in attendance, it was basically a given each of person was actively involved in community organizing and societal improvement efforts. So while the world may try to shit upon trans people, their perseverance responds by aiming to make it a better place.

A few times on a couple of "Native singles" Facebook pages I’ve posted pics of me decked out in a dress and heels. Right away men were asking to "HMU!" (hit me up) “liked” and “heart”❤reacted my pics. Posting on those pages, however, inadvertently became a social experiment regarding transphobia. Like clockwork, some 5-10 minutes later some of those same people would delete their comments and “like” to replace it with a troll-ish “laugh” emoji reaction. Sometimes they’d replace their comment with a transphobic insult, or a GIF about me looking like a man. How so not original.

Likely, they dug through my Facebook profile to find further images of me, and noticed pre-transition pics. While I guess — let's face it — that it is kind of funny, their transphobia that causes them to want to hurt my well-being is guided by a toxic masculinity insecurity that too often leads to tragic consequences.

A lot of men hate to publicly admit they might be aesthetically attracted to a trans woman because they feel it might "make them gay." But gay men aren't usually attracted to me en femme (unless perhaps they already know I am bio male), go figure. They were attracted to my femininity in my pics, not my chromosomes you can't see.

So to counter such anxieties, they may feel the need to lash out violently to prove they’re not. Islan Nettles, a 22-year-old black trans woman who was an assistant at a fashion company, was killed by James Dixon in Harlem. A friend teased Dixon for flirting with a trans woman, so he responded by beating Nettles to death and threatening her transgender friend. The New York Times noted, “For many, her death was emblematic of violence against transgender people, who are frequently the targets of beatings.”

With the memory of Islan Nettles fresh, New York state recently became only the sixth state to ban gay and trans panic defenses. A UCLA Law think tank notes,

“The gay and trans panic defenses allow perpetrators of LGBT murders to receive a lesser sentence and in some cases, even avoid being convicted and punished, by placing the blame for homicide on a victim's actual or perceived sexual orientation or gender identity.”

In a recent viral video, Muhlaysia Booker was viciously beaten until unconscious after a minor traffic incident in Dallas by a group of men chanting homophobic slurs until fellow women intervened and took her to the hospital. A resilient Booker used this incident to bring public awareness to the violence trans women oft face. “This time I can stand before you, where in other scenarios, we’re at a memorial,” she said.

Sadly, her words were prophetic. Five weeks later on May 18, 2019 Muhlaysia Booker would be found murdered on the street.

While the majority of 26 known trans women killed last year were black in what the American Medical Association calls an “epidemic” of transwomen violence,* out of all ethnicities, Native American trans women face the highest rate of it per capita. In a U.S. Transgender Survey, 25 percent of Native Americans had been physically attacked in the previous year specifically for being transgender.

*Trans women are not always listed as such when crimes against them are reported, so numbers are undoubtedly higher.

A selfie of the late Two Spirit/transgender woman Jamie Lee Wounded Arrow, Oglala Lakota.
Pictured: A selfie of the late Two Spirit/transgender woman Jamie Lee Wounded Arrow, Oglala Lakota.(Photo: Jamie Lee Wounded Arrow)

On New Year’s Day, 2017 in the early morning hours Oglala Lakota tribal member and 28-year-old Two Spirit/transgender woman Jamie Lee Wounded Arrow was brutally stabbed by Joshua LeClaire. He claimed she’d made unwanted sexual advances toward him even although he had showed up at her place at 3:30 a.m., and also said a cut on his hand came from her allegedly attacking him. The Argus Leader reported, according to a Detective’s testimony, “the cut on LeClaire's hand was not one of defense from a stabbing attempt.”

Although he’d tried to hint at a trans panic defense as reason for his stabbing her seven times, Judge Bradley Zell sentenced LeClaire to 65 years and straight up told him, “I don’t believe your rendition of facts.”

Jamie Lee Wounded Arrow had hoped to become a counselor and help people overcome their own addiction demons as she had done.

Say her name.

A strange but poignant incident I’ve encountered several times is having friendly female store clerks perhaps compliment me on my nails or makeup along with other small talk, then saying seriously with a fearful concern in their eyes as they handed me change, “Hey, you please be careful out there, girl.”

Such is a reality dose of where we are as a society.

But back to dating, and as mentioned previous, I’m not there right now in wanting a committed relationship. I need to wade in shallow waters before diving in deep despite my life clock consciously tick tick ticking away as I near 40. As much as I miss intimate human connection that manifests to meaningful physical, right now I’m just at an exploratory stage of, "If it happens, it happens."

To a point, I am not lying when I joke to people I’m married to my writing these days — my art. I need to apply my full force of heart into it with my full, rapt, introspective, sober, trans/Two Spirit side. After processing what has transpired between the lines of my experiences via literature, perhaps I can then understand myself better.

When I’ve asked men or women what they found attractive about a trans woman such as myself, there’s a collective opinion of admiration of how confident and “cool” a lot of us are in exuding our feminine selves despite what the general dominant Christian-Judeo colonized society may think of us — especially in conservative areas like mine. But being “cool” about it — as I’m sure many trans women can attest — took courage on a level different than anything I’ve ever done, knowing I’d be isolated from people I’ve known my whole life.

I think of how for years my young daughter was always the ready reason to fend off suicidal thoughts when I didn’t think my own dissolute life was worth fighting for. However, I didn’t want her last memory of me being in a coffin as she wondered why Daddy didn’t love her enough to try to live knowing it would make her forever sad to bury me. But now that I haven’t been able to talk to her in over a half a year since I came out — aside from a brief conversation on her 10th birthday back in February — I helplessly wonder what’s being said about me to her on one of the LGBTQ-phobic eastern Montana Indian reservations she lives on as the solitude of it all becomes unbearably soul crushing as alcoholic “What's the point?” questions and relapse trigger signs flare.

So while some people may admire my courage for coming out, sometimes my cynicism kicks in as I second guess myself. Did I make a mistake? Here I could still be a fairly handsome dude who’d have it easy finding someone relationship-wise as opposed to be being someone now deemed taboo. Or, as I was told more or less a couple of times by non-supportive people, “Well, I guess you should have thought about before you put your kid through this, too.”

But, the thing is, I did think about it. All of my life, I always thought about it. Especially when I didn't want to think about it, I thought about it. I thought about potential consequences, and then quickly looked away ashamedly from the reflection in the mirror — away from the one not fully living as they hid from themselves under a haze of self-loathing and substance abuse. I thought about it, but I came out anyway, maybe hoping I'd be able to fully live with myself.

I wrote a letter to my daughter the other week, telling her she doesn’t need to be scared of me, I am still the same person she still loves — the person she’s always been so proud of when it seemed no one else was — and I’ll always be that same person who loves her back unconditionally.

I told her that I’m not different now, I am just more me.

Maybe someday someone will want to share a life with me, and love that person who is more themselves now. But in the meanwhile, I’ll still carry my head high and regal as my revered and respected Two Spirit ancestors would have done on these occupied Native homelands, seeking a full life that isn’t defined by dysphoria and shame, but euphoria and pride.

Adrian L. Jawort is a proud Northern Cheyenne journalist and writer who lives in Billings, Montana. They are the founder of Off the Pass Press which aims to promote Indigenous literature.

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