Here's what it's like dating while discovering your transwomanhood

Hello Cherry readers!

My name is Sonali, La Niña Fresa, and I will be taking a leap outside makeup to talk about romance. It’s a window peek where you can see that at the end of the day I’m just like y’all: looking for love, kindness, and good sex.

Discovering my trans womanhood has been difficult enough. Since coming out as transgender, male to female (MTF), dating has been a huge learning curve. I was ready for the transphobia from the heteronormative world but, like most things in life, it be your own people. In the middle of learning to resocialize my brain post-coming out, I encountered so much blatant hate and transphobia from my queer community, specifically around dating. For a lot of my friends, both straight and queer, the notion of who I dated and slept with became a topic of concern. To be quite honest, it was easier to date while I was identifying as a gay male.

“The beginning of my femme coming out in Berkeley, CA.” / Photo by  Sonali Tzul

“The beginning of my femme coming out in Berkeley, CA.” / Photo by Sonali Tzul

Granted, for a big chunk of the gay/lesbian experience, you are fighting against the constraints of heteronormative stereotypes. There “has” to be a woman role and a male role filled. When I came out as transgender, everyone had the same question: “Does it make a guy gay if they like you?” This question was something I’d never gave much thought to.

Before coming out, I was living my best Grindr life. For those of you who aren’t familiar, Grindr is a “social networking” app for gay men that recently expanded its horizons to include other identities. I was 1000%broke in college and I had to be strategic about dates. Luckily for me, the guys would always offer to meet at a restaurant and then we would see where the night went.

Besides a bomb meal, a lot of the dates revolved around them expressing how hot my ethnicity and my lips were. Foreshadowing… Not much has changed: Men are weird like that across the board. However, these dates were fine in the sense that we talked about ambitions, where we came from, politics, et cetera. Basically, the dates were not a trial where I had to come out and defend my identity. Gay men would not be ashamed to hold my hand, kiss me, or show me off in public.

Friends would giggle as I told them tales about the guy who played “Friends” in the background, which caused me to laugh in the middle of sex. We’d talk about celebrity crushes, which included all men. It was very easy to talk about such experiences because homosexuallity and queer discourse had been “normalized” in the liberal Berkeley bubble. Dating gay men was a wonderful, validating experience, but there was something missing. Fast forward to me realizing that I would never be fulfilled in a homosexual partnership because I am a trans woman, not a gay man.

“My first time going out as a woman” / Photo courtesy of  Sonali Tzul

“My first time going out as a woman” / Photo courtesy of Sonali Tzul

I remember the first time I came out to a gay man. We were at a gay bar for a local drag show, and I told him. I remember feeling small, stumbling over my words, and avoiding eye contact. I thought he would understand. I thought he could understand. What followed was him expressing how he thought I was already attractive, that he had a crush on me.

When I told him, that I loved men but not in the way a man loves another man, he stared at me… hard. He looked me right in the eyes and said, “You know I think you could make a good woman,” as he grabbed my hands. “But, you can’t do anything about these manly hands or your feet. That’s always a tell with trannys. Your nipples are gonna get all pointy, big, and gross. Do you really want that? You’re gonna get yourself killed! You have to tell guys when you meet them...” I remember holding back tears and zoning out as he kept going.

I looked at him in the eyes and told him with a smile, “I like my feet and my hands. I’m excited for those changes to happen to my body. Who cares if men won’t date me: at least I’ll feel free.” We watched the drag show in silence and he would occasionally bring up another topic around my coming out. It was miserable. After that conversation, he reached out to me less and he stopped responding to me after that, which became the trend with a lot of friends.

“Isolation” / Art by  Sonali Tzul

“Isolation” / Art by Sonali Tzul

The first year of my transition was about getting acclimated to new environments. It was noticing that confused look on people’s faces when I walked into businesses. It was realizing that I was no longer excited to go to gay bars. It meant no longer being “seen” by gay men. I didn’t date — not because I didn’t want to. I just didn’t know how to. Grindr had always been the option, but now gay men with blank profiles would send me toxic messages. I wondered how many of them were my “friends.” A year passed by and I didn’t even try to date. I focused on work and pretended not to notice everybody around me exiting out my life.
After I started wearing exclusively women’s clothing, I felt a bit more at ease. I would go to parties with my biologically female friends. I would physically position myself between them to blend in. I would talk only to them, even if a guy would talk to me directly. I would get hit on and always think, “Dude you’re drunk. Can’t you tell, I’m trans!” If I absolutely had no choice and had to interact with cis men, I would only shake my head “yes” or  “no,” or shrug my shoulders. A lot of times they assumed English wasn’t my first language.

When I started to try and date, I didn’t know where to look. So I went back to toxic Grindr, which by then was re-designed to be trans-inclusive. When the messages started coming in, they were blank profiles — but this time, they were exclusively dick pics. A lot of men were down low, meaning not open to the public, and interested in women. Still, they always asked if my “plumbing worked” and it was always their first time. Yeah, right! Unlike using Grindr in the past, this group of men only focused on sex, never wanted to meet in public, and made sure to always tell me they saw me as a woman. It was always the same type of message, again and again.

“During the time where I was getting sick of men on Grindr :)” / Photo by  Jasdeep Kang

“During the time where I was getting sick of men on Grindr :)” / Photo by Jasdeep Kang

I tried OkCupid and after we’d set up a date, I would ask if they had read my bio. They always said “yes,” because men are liars… And then, I would say something like, “OK, just wanted to make sure you were okay with trans people.” Then, I would get blocked or ghosted. OkCupid was not happening and neither was Tinder. Meeting men in public was not easier. And I couldn’t talk to anyone about what I was experiencing. It was miserable.

I did take some guys up on the offer to meet at their place or have them come over. I would pick only the “best” which just meant the following:

  1. Didn’t send me a dick pic

  2. Didn’t ask about my “plumbing”

  3. Held a conversation that wasn’t about sex

  4. Didn’t overshare just how much they saw me as a real woman

Even still, they just wanted to have sex and then pretend it never happened. These weren’t really stories I could share with friends. A lot of them didn’t know how to handle my trans identity. They just treated me like I was a cis woman, which I can appreciate the effort in, but it still was not the right approach. What it did was silence the fact that I wasn’t cis and that this trans experience was isolating. This whole experience was so new to me — so much that I didn’t have the words to express the isolation.

I stopped dating again — this time to work on my self-expression and figure out how to love myself. I wanted to set boundaries so that men would not walk all over me. And I also didn’t need men to validate me. I needed men to not undervalue me. So... it was a dry ass couple of months.

Then, I went to New York City and something magical happened. I met a guy on the dance floor.

“On the NYC trip” / Photo by  Sonali Tzul

“On the NYC trip” / Photo by Sonali Tzul

At first, I tried ignoring him, because I didn’t want him to feel ashamed that he was attracted to a trans woman. Eventually we started dancing, and talking, and kissing, and holding hands, and laughing. Again, I thought, “Dude you’re drunk! Can’t you see, I’m trans?” But I suppressed that and allowed myself to enjoy the night.

It was 3 a.m. and we decided to get food. We kept talking and for the first time in a while, I felt like I was being seen. We walked around looking at street art while we held hands. We talked about our pasts, but I avoided mentioning that I was trans. He told me how beautiful I was and kissed me passionately. At dawn, I decided it was time to go home. He looked at me as I called a Lyft and asked, “So, is this it then?” To which I replied, “ Yep. I had fun. Remember to be kind to yourself and others.”

As I got in the car, I turned to look at him one last time as he disappeared into the subway. I immediately found him on social media and proceeded to block him. I wanted that night to remain there, as a good memory. I wasn’t clear if he new I was trans. I don’t think he did. I don’t think he inherently had the right to know. I do know that it wouldn’t have made me less deserving of his kindness.

It has been hard finding men who are comfortable being seen in public with a transgender woman, especially in this ever-growing transphobic environment. That impromptu NYC summer spark did two things for me. For one, it reset my notion that men just saw me as something to have sex with behind closed doors. Second, it made me realize that now more than ever, I would need to learn to love all of me. Not just the parts that men want in the sheets, not the parts that cis people welcome at parties, and not just the parts that get me by life “passing” as a cis woman.

I’m still in the middle of figuring out what comes next. I don’t have any insightful closer, but I hope that this has sparked some interest in you to start a conversation.

Thanks for reading.


Sonali 🍒