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🔒 Up next for paid subscribers: Next week, I will be sharing about my relationship with sex and navigating the first date.
A Conversation with My Therapist
“Why do you hold yourself back?”
I stared at my iPhone, processing the question my therapist had posed.
I had recently signed up for Talkspace, encouraged by a coworker who told me our company's insurance was accepted there. After a year without therapy and a recent breakup, I was ready to try again. At $15 a session, it felt like an easy choice.
I hadn’t had many therapists, but this felt like the first time someone was really listening. With a deep inhale, I began sharing my story—releasing years of frustration and flawed beliefs that I’d carried alone.
To explain why I hold myself back, I had to go back to one night in 2018.
The Moment that Masculinity Became a Villain
I was 22, only a few months on testosterone, when someone first told me I was no different from a cisgender man. At the time, it felt validating.
Later, those same words became a source of shame.
It happened on a first date.
We had matched on Bumble, and after some solid conversation, agreed to meet at a sushi spot in SoHo. I arrived early, secured us a table, and sipped on ice water while waiting for her.
The door opened. She stepped in: bright patterned dress, silver accessories, Doc Martens. I waved to catch her attention; she waved back.
“Sorry, I’m late! The E train had serious delays at Canal Street.”
I smiled and brushed it off. “It’s all good. We all know the MTA’s a mess.” I had a habit of trying to lighten the mood on dates, to make things less forced.
We ordered our food: salmon avocado rolls for me, salmon teriyaki for her. Conversation was light at first. Work, our weeks, the usual small talk. Then the food arrived, and the conversation shifted.
She started talking about toxic masculinity. About her past relationships with men who wanted a mother instead of a partner, who were emotionally unavailable, and who did not even care for themselves. I nodded along, listening intently.
As someone assigned female at birth, I could empathize. And yet, something about her words rubbed me raw. I could not name it, but I felt it.
When her rant slowed, I reached across the table to touch her hand, just to offer reassurance.
She pulled her hand back. “Wait, what are you doing?”
I froze. “What?”
Her frown deepened. “I was telling you about how these men treated me, and you wanted to do that?”
Panic surged. “No, no, it is not like that. I was just trying to offer some moral support.”
She sighed, her face softening slightly. “It’s okay. I just thought you were different. But you are no better than the guys I’ve dated.”
Ouch.
She might as well have put on boxing gloves and punched me in the face. Those words circled my mind long after the date ended.
We finished our food in relative silence. I knew there would not be a second date.
The next morning, her text came through: Had a great night, but I don’t want to go on another date. Hope we can still be friends.
I replied with a few words and pressed send:
Yeah, sure thing.
The Aftermath
Her words became an invisible backpack I carried everywhere. They convinced me that masculinity itself was dangerous. That I should feel guilty for my desires, ashamed of my needs, and punished for what other men had done.
When the #MeToo movement gained traction, that backpack grew heavier. The last thing I wanted was to make anyone uncomfortable, to ever be seen as a creep. So I did nothing. I avoided making moves with crushes unless I had a clear green light. I told myself every smile or laugh was just friendliness, not attraction.
To protect myself, I leaned into a more flamboyant personality, hoping people would see me as safe. Instead, it led many to perceive me as gay rather than pansexual.
In the end, I figured it was safer to hold back than risk hurting someone.
Returning to Masculinity
“…and the rest is history, as they say.”
I ran my fingers through my hair, finally exhaling as I finished the story for my therapist. I had never shared this out loud before—naming it felt like a small release.
She nodded gently. “Given your lived experiences, being trans, not having strong male role models, and internalizing messages that masculinity is bad, it makes sense you would carry this. But let me ask: do you think you are a bad person for being masculine?”
It sounded like a simple question, but it had layers.
I knew, deep down, I was not a bad person. And yet, I still wondered: would people I love understand that if I dropped the mask? If I showed them that healthy masculinity is not bad, that it can even be tender?
I took a breath. “No, I am not a bad person for being masculine.”
I could almost hear her smile through the phone. “No, Rey. You are not a bad person.”
Unpacking masculinity is a journey, and we all have to start somewhere.
What does healthy masculinity look like to you?
Share your thoughts in the comments. I’d love to keep this conversation going.
I search for non toxic masculinity as well. Although, for me, it’s more toxic people vs non toxic people. Gender is irrelevant. I search for Humanity.
I call myself a gay transgender man. I have a uterus. I have born four children. I do not feel like a woman. I don’t know what those terms mean. Woman and man. We are all humans. Some with uteruses. Some with testes. The range of possibilities is endless because humans are as varied as stars.
Thanks for sharing this. I think what comes up for me is that so many of us are just walking around with the baggage of our pasts in a context of a sick and dysfunctional society. Including your date, including you, including me and my husband. Cis, trans, and everything in between. I know that's super general, but that's what this sparked.