A trans man’s guide to dating straight women (part 2)

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So a while ago I wrote an article on dating straight women as a trans man and have been thinking, there’s a few things I’d really like to add to this.

I still 100% stand by everything I wrote and it’s really great to hear that so many people found it a helpful read. This “guide” is obviously not for everyone and every individual needs to navigate this space in their own authentic way. I certainly do not profess to have all the answers and can only speak from my personal experience.

As I talk about in the previous article, I don’t identify as being trans the way a lot of trans people do, I just am. And this means I do navigate my being trans differently to many.

In all honesty, I really savour those first few dates, where I’m connecting with someone and to them I’m just like any other guy. But there is always that edge of not only knowing that you have to tell them soon, but the physical and emotional restraint that has to come with this. I do sometimes really wish that I could do that impulsive thing of just ripping each other’s clothes off on a second date, and it really does break my heart that some women do misinterpret me wanting (needing) to take things slow, as a lack of sexual chemistry, either thinking that I’m not attracted enough to them or that they’re wondering why they’re not feeling like ripping my clothes off.

On that later point I’d say I’ve become pretty adept at sending subtle “please don’t rip my clothes off” signals to women, which they’re not necessarily picking up on consciously, but do respond to unconsciously. Though not always… I did once have an experience with a woman I dated very briefly, where on the second date we somehow ended up in her bed and for her, there was only one way this was gonna go. I had to really put the brakes on very hard with a “wait, wait, there’s something I need to tell you…” After I did, her reaction was literally “meh” and she proceeded to continue to rip my clothes off, which was actually pretty awesome. I will always be eternally grateful to this woman for how completely non-plussed she was by me being trans, and it is a shame that for a variety of other reasons we couldn’t work out.

The other kind of restraint is the emotional kind. I do always feel like I’m walking this tightrope where I want to be able to let myself go enough to be in that moment and really let myself explore how I’m feeling about this person, but need to hold myself back enough, that if it turns out, me being trans is a deal breaker, that I don’t get destroyed.

I once had a woman say to me “you are just such an amazing guy and I love absolutely everything about you, but I do wish, both for you and for myself, that you weren’t trans.” As much as I understood her sentiment, as I’ll honestly admit, I wish this too, this person fundamentally missed the fact that I am the person I am BECAUSE I’m trans. It’s my life experience that has made me who I am. That is a person I am very happy and proud to be. Yeah, sure I wish I had a biological penis, but in all honesty, I don’t think I’d be anywhere close to the person that I am today had I had a privileged, white male, heteronormative upbringing. Today I can honestly say that 80% of what has been the direct result of me being trans is actually pretty positive and it only 20% blows. That 20% is in part made up of the occasional dating rejection. Of course, being trans is not the only reason I may get a rejection, but it’s the only one that really stings. I’m totally fine with a rejection based on, say, the fact that I don’t want to have kids, or pretty much ANY other reason.

“I am the person I am BECAUSE I’m trans. It’s my life experience that has made me who I am. That is a person I am very happy and proud to be.”

Thankfully in my experience a rejection has been the exception not the norm, but when it does happen I can’t help but have to do a post mortem on the situation.

So based on my last experience which I guess I’m still in the middle of processing, and in addition to what I say in my previous “Trans mans guide to dating straight women” here’s a few suggested don’ts.

Timing is a pretty important factor in terms of how this “I’m trans” piece of information is received. I already talk about this in my previous article, but in addition to that, I would highly suggest NOT telling them when you’re in the middle of making out. Do it in a park or over dinner, ideally with no alcohol involved. But not while you’re horizontal on a sofa, because you’re feeling pressure to take things further.

It’s been my experience in the past that as much as women generally WANT to instantly be fine with this piece of information, that’s just not how it works and it takes absorbtion and processing time and gentle navigation. If given this time and if there’s genuinely already a connection there, my experience has been that they will be open to exploring things further.

And secondly, as well as honoring their feelings and response to the situation, whatever that may be, honor yourself! Immediately after telling someone your biggest vulnerability*, you’re gonna feel naked as hell (and not in a good way) and that is absolutely not the time to take things any further. In other words DEFINITELY keep your pants on when you’re feeling at your utmost naked, scared and vulnerable.

*I’m speaking for myself here, and I acknowledge that there are plenty of trans men out there reading this that are thinking “what the hell is he talking about??” (If that is you, I truly envy you.)

Anyway, I knew that night last week, after I told her, that things had flipped for her very suddenly and that was confirmed yesterday. She really did try to be super sensitive in letting me down, but it still stung like hell.

But thankfully I have had enough positive experiences by now to know that this is not the way it’ll always go and hence I know I’ll bounce.

I can also honestly say that even though being trans has been a factor in relationships not getting off the ground, it has NEVER been a factor in a breakup.

So I guess I also just want to say to everyone else, that yes, having a person reject you due to being trans really, really blows, but being trans is also an important part of what makes you, you. Let that make you a stronger, more insightful, thoughtful and resilient person and don’t let a rejection stop you from letting the people you care about see you… really see you… as hard and scary as that sometimes is. Stay open. I promise, with the right person, it’ll be totally worthwhile.

PS. I’ve since written a follow up blog post “A trans man’s guide to dating straight women (part 3)”.
2022-06-01T13:20:15-06:00January 18th, 2018|Dating, All, How to's/Tips and Tricks, Media/Social/Politics|16 Comments

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  1. Charles March 20, 2018 at 9:48 am - Reply

    Thank you I always look forward to your emails like this. They help me so much. Thanks

  2. Alix March 21, 2018 at 3:29 am - Reply

    I’m sorry dude! It happens to all of us, but glad to see you’re taking it in your stride. Put good stuff out there and it will come back atcha! It’s a karmic law (or some such?? ;)

  3. Shauncraft March 23, 2018 at 4:06 am - Reply

    Reading this out of pure curiosity as I’m a gay dude. I also don’t want to identify as trans.

    Thanks for sharing. It gave me some insight.

  4. Jesse March 23, 2018 at 4:34 pm - Reply

    I transitioned when I was in a lesbian relationship, and that relationship didn’t survive my transition. I also thought I would simply be alone for the rest of my life. Wanting to do something useful with my life, I started volunteering at the hospital. There was a young women who was also volunteering there, on the Saturday night as well. Because hey if you are going to be alone for the rest of your life, you may as well spend Saturday night in the emergency room every week. We chatted every week for the half hour that our shift overlapped. It didn’t even occur to me that she was interested in me, but she became a friend and we started having the occasional coffee together outside of the hospital. Several months went by, and one day she told me that she had feeling for me. I figured the conversation would be over when I told her I was trans, but all she said was “I know”. This really shocked me, because I had been passing consistently in every facet of my life for over a year. But she had googled me, and I had written some articles about transitioning in the workplace. I hadn’t noticed, but she had taken a few weeks off from seeing me to process the fact that I was trans and to think about whether or not she could be with someone who was trans. She decided that she could, and we now have been married for 9 years and have a 5 year old son. I know that I am really lucky and that not everyone is this fortunate, but I think most heterosexual trans guys will be able to find women who are understanding, and who just don’t care about the minor details like the length of your penis.

    • Alex March 23, 2018 at 4:38 pm - Reply

      I love this story so much :) Thanks for sharing, Jesse!

    • Matías May 22, 2018 at 4:21 am - Reply

      This was so moving. I felt very, very identified with this for the simply fact that I’m a straight trans man who is somehow afraid of being alone. Thank you for sharing your story, Jesse!

    • Flow September 23, 2018 at 3:42 pm - Reply

      Did you get bottom surgery done?

    • AL October 13, 2018 at 5:13 pm - Reply

      That’s awesome!!! ????????

  5. J April 9, 2018 at 3:30 pm - Reply

    thank you for writing this.

    “after telling someone your biggest vulnerability* I’m speaking for myself here, and I acknowledge that there are plenty of trans men out there reading this that are thinking “what the hell is he talking about??”

    as completely stealth transman, I know exactly what you mean.
    actually as result of my intense fear of being rejected, I kind of gave up hope of ever finding someone.
    I live my life as a man not as trans, and in all my interactions with people I act as if I was born male, and my dysphoria is bad enough, I don’t need on top of that to trust someone with my secret and then get rejected.
    so it is much easier for me to accept being alone,I guess this might has to do with a combination of being trans and having INTJ personality.

    • RJ April 15, 2018 at 1:41 am - Reply

      ha, another INTJ stealth trans guy here, I struggle with the same thing. I think we are a rare breed (actually, I am quite positive, given the prevalence of each alone), which makes it more difficult in a way. I have to constantly remind myself that there must be at least one other person in the world in my situation…

      It is easier to accept being alone but then I start to wonder if in the long term I am letting being trans dictate/limit my life too much. I don’t want that to be determining my life to that extent, and in a negative or limiting way, you know?

  6. Michael May 19, 2018 at 7:50 pm - Reply

    Is there a way I can contact the person who wrote this article? I am a stealth trans man and have avoided dating for a long time due to my own fears and insecurities. I would like to get some advice from this guy.

    • Alex May 21, 2018 at 9:11 pm - Reply

      Hi Michael, There’s a bunch of trans forums and support groups on Facebook, Tumblr etc that I’d recommend reaching out to, seeing we’re all in similar boats :) I’d just say the best thing is to face your fears. Go on a few dates. Don’t put too much pressure on yourself or the date. See these dates as just getting your feet wet and seeing what it feels like. I think you might be pleasantly surprised :)

  7. Jesse R. July 8, 2018 at 1:54 am - Reply

    This was exactly what I needed to hear at exactly the right time! I’m 53 and just passed the first year on T. For reasons I won’t go into here I’ve been having to deal with accepting I likely won’t be having further surgery, meaning that though I pass because of T and top surgery, I will need to learn to live without even coming close to passing when naked. I was also thinking I’d just have to accept being alone too, but this (and the previous) article have restored my hope. THANK YOU ALEX!

  8. JAY October 21, 2018 at 6:03 pm - Reply

    Hey, great article, totally relate. is there anywhere I can get some good tips. Advice or jacks on using The Joystick, or even traditional strap-on sex for a trans guy dating a cos woman? (keeps spellchecking the ‘sis’ big their for some reason) I’m really struggling with it and it’s sending me into a total spiral ofselfdoubt and self loathing. Any pointers the right direction would be so gratefully received. Thanks boys :$

  9. Anna March 14, 2019 at 4:22 pm - Reply

    I’ve met a lovely guy, he seems amazing and I’ve defo fallen for him. He feels the same and wants a relationship, however sex is holding me back. I obviously know there are areas he doesn’t like touched ( we have spoken about sexual likes and dislikes ) but I really have no idea how to be intimate with him. I really don’t want to offend or upset him and well I also want to please him.
    If we start to get intimate will it be appropriate to ask him to help show me how he likes to be touched etc? Or is that weird?

    • Alex March 14, 2019 at 5:18 pm - Reply

      It’s really all about communication. Talk to each other about your wants, fears, insecurities, doubts, wishes etc. I can’t profess to know what it’s like for another trans guy but for me personally, it’s important to feel that my partner accepts and enjoys my body, as that’s a very difficult thing for me to do and knowing someone else can, makes it possible for me.

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