April 1, 2018



A story of youthful ignorance and heavy drinking

I went on a date with a Trans guy. It didn't go great, but probably not for the reasons you're imagining.

Stories of queer life and even queer-er sex.

Always interesting, definitely amusing, Probably True - the repeatedly-award-winning, slightly filthy storytelling project tackling LGBTQ issues in a fun and engaging way.

Much like its creator, it is a smutty-but-charming collection of personal misadventures working to make the world a better place, one silly, sexy story at a time.

Patreon.com/ProbablyTrue //  @ScottFlashheart


Theme music is 'RetroFuture Clean' by Kevin MacLeod 
Licensed under Creative Commons by Attribution 3.0 License  

See acast.com/privacy for privacy and opt-out information.


Soooo last week I did a Q&A session, and part of one of the questions I got asked was “Have you ever been out with a trans guy? And I said I’d tell you all about it this week. So, here we go…

Yes, I’ve been on a date with a trans guy. You’ll never believe what happened. It was fucking shameful. I was so embarrassed. He’s a filmmaker, and we met at a showing of one of his films, swapped numbers and agreed to go out for a drink the following week. I know you’re all dying to know what happened, so I’ll cut straight to the chase. I, right, me, right here, got drunk and made a tit of myself. But Scott, you might be thinking, that’s just like every other date you go on. we were expecting something different! 

Oh, really? Why?

If you thought this was going to have anything but exactly the same outcome as any other date I’ve been on, then that says a lot more about you than it does about me. And all it says about me is that I’m borderline alcoholic with iffy social skills and a probable future of dying alone. None of which is news. I mean, pretty much all of my podcasts up to this point will tell you that. But I’ll take all of that over being weird about trans people. I know a lot of people who aren’t trans have a bit of trouble with this, so let’s try something.

If, just for a second, you ignore the ‘trans’ part, then you’re left with ‘people’. Try and focus on that bit. If it helps, try turning it around, so rather than your brain getting stuck on the ‘trans’ part of ‘trans man’, and not getting any further, how about “I went on a date with a man who happened to be trans.” The important part shouldn’t be the trans bit. As a white guy, I wouldn’t say, for example, “I had a night of fantastic sex with an Asian guy”, or “I almost got engaged to a black guy” because the ethnicity of the guys shouldn’t be news in this day and age. And while racism and transphobia are very, very different things, the point I’m managing to mess up is that we’re all people and should probably focus on that bit. 

And if you’re the sort of person who says “I’m not transphobic, but I’d never date a trans guy - I wouldn’t date an Asian guy either, and I’m not racist.” then I have two pieces of bad news for you.

Let’s use this as a bit of a learning experience. If fucked this up once, so you don’t have to in the future. If you’re going on a date with a trans guy, don’t ask any questions about their life, pre-transition. Don’t ask what his name used to be, or how long he’s been transitioning, or anything like that. On no account start a question with “When yyou were a woman…” because he never was. He was always him. 

I went on a date once with a guy who kept asking really insistent and probing questions about any childhood traumas I might have had, which I was uncomfortable with. When I asked him to knock it off, he complained that he was “trying to create an intimacy between us”. Personally I’m not that keen on forcing an intimacy with someone I only met half a bottle of gin ago. Asking questions about a trans person’s life pre-transition is even more invasive and none-of-your-business than that. 

When you’re on a date, if the only thing you can think about the other person with you is “I hope this person has exactly the kind of gentials I’m currently imagining” then you shouldn’t be on dates with anyone, ya weirdo. Date people because you get on with them, you like their personality, you’re fairly certain they’re not going to be scared off by the huge collection of emotional problems you’re hiding beneath the surface, not because you think you know what their crotch looks like.

I got drunk and made a tit of myself in front of a boy who just wanted to be treated like everyone else because I didn’t know any better. But now you do, so hopefully you’ll handle things better than I did.

He was gorgeous. Fantastic kisser, and drank me under the table. All of which are qualities I look for in a lover. He got married last week, actually. So choosing not to see me again turned out to be the right call for him. I mean, I’m sure the same is true of most of the people I date, but I don’t want to think too much about that, to be honest.

Before I get too distracted talking about my failure to relate to humans, at least until my mind-control device is complete, I want to look a little at the rest of the question - we’ve covered whether or not I’ve dated a trans guy, so that leaves “Do you think a trans guy has any kind of chance in the eyes of cis gay men?” and there’s a few things I want to address there. I’m going to go a bit Dan Savage on yo ass. Or vagina.

That question, as you ask it, is the wrong way around. When you ask it like that, you’re saying “Oh, do you think someone as awful as me could have a chance with someone as wonderful and lovely as those cis gay guys?” Which is entirely inaccurate. You are awesome, and an amazing person. You’ve already some something so amazing and brave and life changing by coming out as transgender, or non-binary, so there’s no need for this kind of thinking. Turn that question around: Which cis person, if any, deserves a chance with me? Give yourself the power to decide who is worthy of you, and your affections. You do not feast on the scraps of affection thrown to you from cis men. You do not wait to be noticed, in the hope that someone, somewhere, might find you not repulsive.You are better than that. Allow yourself to approach this from a position of self-love and empowerment. DEcide what you want and go and get it.

Instead of “Do you think you could lower yourself to possibly perhaps liking me?” say “You there. I’m amazing, and I think you might be, too. Let’s find out, shall we?” And those that you choose are lucky to get the opportunity to impress you. If they decline, or fall short, then that’s their loss, not yours. You are worth more.

There will be rejections, of course. Not everyone who seems amazing really is. And sometimes they are but it’s just not a good fit, or, more likely, they’re not, but we try to convince ourselves that they are. And that’s hard. It takes time, and a lot of self-love. After the first few hundred knock-backs, you start to learn how to deal with it. I wish I could tell you it gets better. But, like the late, great Joan Rivers said, it doesn’t get better. You get better. And to do that, you have to learn to love yourself, and see yourself of worthy of whatever you want.


You’ve already done the hard part - once you start speaking your truth and living an authentic life, you’re well on your way. And anyone who stands in the way of you doing that can shove it up their arse. Or vagina.