The Male and Female Gaze, from a Trans-Masculine Perspective

(Part 3 of 6)

Orlando G. Bregman
9 min readSep 4, 2024
The Author, Orlando G. Bregman in 2006 at lawrence Ferlinghetti’s City Lights Bookstore, North Beach, San Francisco. (Picture taken by my father Abraham “Bram” Bregman.)

By Orlando G. Bregman, November 17, 2023

(They/He)

(Originally written in late 2019 and saved as a draft on Medium but completely forgotten to publish due to the COVID-19 pandemic, and my mother’s death from it in late 2020, so now slightly updated in late 2023 and published finally in mid-2024.)

My name is Orlando G. Bregman, my pronouns are They/He, meaning I prefer they over he but will also respond to he, and I identify as, or simply am trans-masculine, gender nonconforming, and lesbian. (And I do not personally feel the need to medically transition.)

(Part 3 of 6)

(Click here for Part 1, Part 2, Part 4, Part 5, Part 6)

Regarding the LGBTQ concept of “Flipping the Script”.

ON “FLIPPING THE HETEROSEXUAL SCRIPT”, FROM A TRANS-MASCULINE POV.

Gay and lesbian people have often described watching and enjoying heterosexual film narratives not made for them, and in more closeted times in history, as having mentally “flipped the script” in order to project their own desires onto the story lines, since their own story lines and accurate homosexual representation was missing from the screen. And I do in fact remember these times myself.

But for a transgender person, specifically in the days when there where was hardly any representation in media and in real life available, or of an exclusively implicit or negative nature, in my own time included, this mental process was slightly more complicated, or somewhat simplified, depending on how you look at it.

For me personally, although assigned female-at-birth, it never felt like I mentally “flipped a script” in order to imagine myself “as the male character” in order to be with the female character romantically or sexually.

As a trans-masculine person who has always been exclusively attracted to women the existing scripts in heterosexual film narratives always felt entirely natural to me, and I always identified rather effortlessly with the male characters in films that I liked.

I did not think about this consciously, certainly not as a teenager in the 1980s, and watching films for me started well before any sex education, which when given in high school only included heterosexual education. Sex education in my high school in the mid-80s did include cautioning against AIDS though, but this was the only implicit reference of homosexual existence, as in if you “choose the homosexual lifestyle, you’ll catch AIDS and will die from it.”

To top it off many films have either way been written and directed from male perspectives, so that even women are forced to identify with the leading men who were the protagonist of any given story, or else necessarily project themselves onto secondary characters, as female love interests, as that would be their only other option, to identify with an “object of desire” exclusively, besides tuning out and not watch films altogether of course. Surely many women, mostly heterosexual ones, have identified with “the object of desire” exclusively, and have in fact lived their whole lives that way, wrongly assuming their role and purpose in life is to be a man’s object of desire, with inevitably disastrous consequences.

So basically watching films for me, as a trans-masculine person who was attracted to girls and women only, was essentially an entirely pleasant experience in my childhood in the 1970s and 80s, despite the severe lack of LGBTQ representation.

The “flipping the script” part only became an issue of sorts since I started to understand how sex worked, heterosexual sex that is anyway, but since in most films no real sex was actually shown, or nothing even close to it, at least not in Americans films, it was as suggestive as my imagination, because the films only got around any heterosexual intercourse, and therefore so did I in my mind.

Europeans however, in film and in life, got to the sex way more, and differently than Americans, and way more explicitly, and this was both more exhilarating and shocking as this is where things got slightly confused for a 12 year old me. Things started becoming problematic around puberty, especially since not knowing consciously what transgenderism, or being transgender, was. I didn’t exactly experience myself as being in a wrong body, or as trapped, but I most definitely felt a strong disconnect.

And I also didn’t initially know I was feeling that even, or that other people didn’t feel the same, and figured I was just a misunderstood teenager. For a long time I felt perfectly fine “being James Dean” in Rebel Without A Cause or “being Dennis Hopper or Peter Fonda” in Easy Rider or “being Robert De Niro” in Taxi Driver even. Watching films was mostly a private experience for me, other than initially being introduced to them by my parents. But it was certainly not a dating experience, as watching films in theaters, especially outside of Hollywood, were often experienced by heteronormative people.

Once lesbian content was slowly introduced to me, first mostly through literature as I was an avid reader as well but increasingly through film, beginning most consciously in my mind with the 1991 release of Philip Kaufman’s Henry and June, when I was 18 years old, just out of High School and already steeped in art films by then, this was also both exhilarating but confusing to me personally, and not because I felt any shame or guilt for being attracted to women, which I did not, probably exactly because not identifying with women. It was most likely for this reason that I did not immediately realize that someone identifying as gay had to customarily “come out of the closet” and eventually “find a gay scene.”

I just lived my life as a person dressing and behaving masculine and being attracted to women and personally thought nothing of it, or how truly different this made me compared to my peers and surroundings. I started to sense it was not considered the norm however and something to be hidden, through other people’s disapproval of me, but I did not actually conform to them nor did I feel any shame or guilt around my sexual and gender differences.

The idea of two women together was definitely a turn on but I did not easily or readily identify with a woman. In the case of Henry and June it was manageable because of the way it was told, from a writer’s perspective, and I was already a writer by then and I could therefore project myself onto the Anais Nin role, as the writer and through whose gaze this story therefore necessarily was told. (And the exact same dynamic was at play for me mentally years later while watching and loving Todd Haynes’ Carol.)

Yet I did not actually relate to Anais Nin in many other things I considered feminine. I exclusively related to her for being an artist, and even to the extend that she was disrespected and overshadowed by Henry Miller for it, and definitely to her being in love with June Mansfield, Henry Miller’s wife. Also Anais Nin introduced journal writing to me, while Jack Kerouac introduced stream of consciousness to me, and together they helped save my young life.

Revisiting my old street Horizon Ave. from 1993 in Venice Beach, CA in 2016 for my documentary F-1 Dutch Film Student in 2016. (Picture by Mario Luza)

But genders, and the societal roles expected from them, just started becoming clearer, and more problematic, through observations, whenever social time was actually required.

Around age 12 or 13 I started noticing how other people seemed more connected in general, more comfortable expressing themselves personally and interacting with each other socially and sexually, and altogether more adjusted to the world, and outwardly seemingly happier, because of it. I on the other hand was introverted, private, awkward, seemed distant, anti-social even, though not consciously depressed, not lethargic, and also not overly aggressive, or violent, or maliciously rude even, just extremely creative and mostly intelligent enough to keep up with the pack, yet socially “not all there.” And so I increasingly started avoiding people and social occasions, especially if there was room for the conversations to turn to gender somehow. And as I found out, just about every conversation in the world sooner or later involved gender.

And people were necessarily mis-gendering me, even if I didn’t have that word for it myself yet, but it started causing me a great deal of social anxiety, which I only much later recognized as social dysphoria, an outward form of gender dysphoria, as opposed to body dysphoria, the type of gender dysphoria most focussed on, which is much more internally felt and specifically towards one’s body or certain body parts, although not entirely without the help of negative outside influence either.

In fact, most of the things we do and say and even feel throughout our daily lives are gendered, or at least perceived as such. When you are cis-gender you probably just notice it a whole lot less, if at all, although any woman at some point will come to realize her perceived inequality in society as well, but if you’re transgender or gender nonconforming you definitely get triggered on an almost continuous basis by these insistences from others existing contently in an exclusive gender binary system and their prescribed gender roles.

But I wasn’t aware of any of this on any real conscious level growing up, not of other people gendering everything nor of me escaping everything to do with distinct genders, like shopping, clubbing, sports, hospital visits, and of course dating, and even every conversation as soon as it turned to gender, like expectations around family life, professions, attractions, and all kinds of general interests ultimately. I just blocked everything and retreated in art.

Growing up in my very liberal home country, the Netherlands, I did still learn slowly but surely that women, including all female-bodied individuals, and so myself included, were expected to plan their lives around some husband, to whom children were owed through some biological duty, instead of a career or a profession, or even an education. And I learned this the hard way in Hollywood, starting with Film School in 1992, through people questioning and doubting and discouraging for the last three decades my absolute certainty and confidence as an artist.

I just didn’t truly think growing up that I engaged in any sort of anti-social behavior though and just thought I liked watching films a whole lot. I actually figured the other kids around me were just ignorant and slow for not appreciating films and literature and music quite as much as I did. Most kids in the Netherlands grew up on sports over art or entertainment even, especially soccer, and then switched to going clubbing and drinking when a little older, as far as I could see.

But after High School I started hanging out with an alternative crowd of artistic, often queer, individuals in a video production course I took in Utrecht, in anticipation of going to Film School in the US. They were the cool kids in my mind but in reality mostly outsiders, borderline punks, dressed in black and with ripped jeans and Converse sneakers, living in decrepit apartment without working heaters, using wooden pallets for beds, with knock off Warhol paintings on the wall, and obsessed with Morrissey, The Cure and New Order, while I personally gravitated more towards classic rock like The Doors and The Rolling Stones and Led Zeppelin however, and was deemed slightly too commercial for it by them.

It would actually take me decades to realize I had literally used films, as well as books and music, as a way to “live,” as a substitute for life really, for a life I was not completely able to live out in reality. And that the only way that I would have been able to keep “living,” since I couldn’t literally live inside the movies or books, and I would have to get a job at some point anyway, was to make them, to become a filmmaker and a writer. To become the director of my own life in a way, to find an actual way to make my own choices in life, since there had been no real ways paved out by society for transgender people to live out our lives, and the wrong expectations have been continuously projected onto us, psychologically suffocating us.

To become a filmmaker and a writer was a matter of life and death, just as watching films and listening to music and reading books, and through those things imagining myself moving about through life as male completely and without any external resistance or confusion, and being able to breathe that way, had always been a matter of life and death. And therefore Hollywood became my ultimate destination, and Venice Beach the place to live, because Hollywood is where they made films, and Venice was where certain Beat writers had lived, and The Doors were from, the final frontier and hippie center of the West, as I was made to believe.

(Part 3 of 6)

(Click here for Part 1, Part 2, Part 4, Part 5, Part 6)

Orlando G. Bregman

(They/ He)

Writer/Publisher at The Auteur

Documentary Filmmaker at Bregman Films

All Rights Reserved (2024)

Click here for a List Of Essays

Revisiting the European Youth Hostel on Brooks Ave. in Venice Beach, my first place in the US in 1992 after Film School acceptance, for my documentary F-1 Dutch Film Student in 2016.

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Orlando G. Bregman

Essay Writer TRANS-MASCULINE IN HOLLYWOOD/Documentary Filmmaker F-1 DUTCH FILM STUDENT/Founder THE AUTEUR Film And Identity Publication & Film Org (2024) TM