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A guide to dating as a trans woman

Navigating the dating scene when you’re an ‘acquired taste’ can be difficult – here are some tips (coming from admittedly quite the straight girl perspective)

I’ll be honest: I’ve never been a huge fan of the concept of ‘dating’. You roll along to some cafe or pub, nervous to meet a stranger whose use of Instagram filters is deft enough to have convinced you they look like a human being, and who you believe to be interesting because they say they like reading and travel. (Does anyone hate reading or travel? Would anyone, if given a plane ticket to anywhere in the world say “fuck off mate I despise travelling”?)

After necking a glass of wine or two you start talking about yourself – trying to impress while not sounding like a moron – and assessing whether or not this person is a total dud, whether you’re feeling disinhibited enough to let them feel you up a bit or whether you’re besotted. I’ve never been besotted. But despite all this, I have dated and am doing so at the moment because it’s the best way to meet people if you’re a niche market, and there’s nothing more niche than trans women. We are the obscure progressive jazz album of the modern dating scene, the acquired taste, the blue cheese. One of the things people ask me most about being trans is what sex and dating are like, so I thought I’d spare myself the repeated conversation and share my experiences of attempting to date as a trans woman here.

I am bi, but – in truth – have currently only been dating men. There are great tips out there for trans lesbians who are looking to date, but I will confess I am cursed with an attraction to men, sadly, and so this is quite the straight girl perspective.


One of the weirdest things I have found myself explaining to cisgender friends in the past year is that I would not be expecting to date or have sex with gay men. I used to, yes, but that was because I was living in the wrong gender role, honey. Gay men are attracted to men and often to the physical signifiers of masculinity. I am spending quite a lot of money on hair removal and growing a pair of tits – why would gay men be attracted to someone who is female? One of the big adjustments in transition if you previously lived as a gay man is realising that gay men are not your dating pool any more. It’s a shame, as I like gay men a lot and, of course, there are some self-identified gay men who will take a dip in the bisexual pool, but on the whole I’ve literally kissed goodbye to the gays and become the world’s largest fag-hag.

Another thing I have to explain is that attraction to a trans woman doesn’t make a man gay. Sometimes you even have to explain it to the man himself, which is very tedious. Two weeks ago a drunk guy made out with me in a club then asked if it made him gay. I replied “No, it doesn’t make you anything. It’s not all about you.” As I have written before, transgender porn is the only area of the commercial porn industry not in recession. There are literally millions of straight men who find trans women arousing – maybe even your dad, for example.


Sadly, this is something trans women share with women in general. Yes, it’s an honourable mention for the damn patriarchy – which teaches many men to expect women to all be slim, under 30, hairless and willing to behave like a cock-hungry nymphomaniac on cue. Part of the problem is that sometimes porn is the only lens that men have seen trans women through, and they forget that any woman in porn is presenting a fantasy. Most of the time when I am talking to men on dating apps, I am sweeping pizza crumbs off my chest on the sofa. I am not curled seductively like a Victoria’s Secret model cooing with delight at whatever flaccid dick pic a man has decided to bestow upon me without even a ‘hi’. Sometimes, men find this disappointing.

It’s also important for your self-esteem to get a sense of whether a man would actually be seen with you in public. A lot of men are ashamed of their desire for trans women, and it’s important to swerve them no matter how much they call you beautiful from behind a blank dating profile. Even this isn’t always foolproof. Meet this guy below, who asked me out on a date a few weeks ago then told me just as we were arranging it that he already had a girlfriend.

Dating as a trans woman involves placing a high degree of self-worth upon yourself and your time, ladies. Of course, a sneaky fumble with a man can be fun if you just want sex, but it’s important to remember you deserve the basics of respect for the fact that you are not just some exotic fetish.


This is a matter of personal taste. Some trans girls get a standard dating app like Tinder and choose to disclose the fact they are trans on a need-to-know basis. I personally would rather not talk to someone for ages before the potential for them to go nuclear and call me a deceptive freak or some other charming form of abuse when I mention the teeny, tiny fact that I used to be a boy. So, as a result, I say I am trans right off in my bio – if a man decides to talk to me then I don’t have to be anxious about disclosing. There’s also a greater chance he’s already considered having sex with or dating a trans woman.

The other option is using the ‘trans’ filter on apps usually used by gay men, like Grindr. This has the benefit of ensuring men you speak to are looking for a trans woman specifically but it does also have downsides. Gay apps refer to all their users as ‘guys’ and it’s clear that some men don’t get the difference between crossdressers (men who like to wear feminine clothing, sometimes in sex) and trans women. If you use an app like Grindr, it’s also likely that men will be expecting you to have a penis – which not all trans women do. In trans porn it is quite common for the trans woman to be the ‘top’ (she will fuck the guy), and it’s clear this is what a lot of men want on hook-up apps. If you’re into that then it’s your lucky day, but if you would perhaps like to just go to Pizza Express and have a conversation, sometimes this can be irksome.


This is where I have to be everyone’s cool mum. Trans girls are at the same risk, if not more, of exposure to HIV as gay men. HIV awareness in the LGBT community and beyond is already pitiable, but what little sexual health advice there is tends to be all aimed at gay men, and we get forgotten. Trans women should be using condoms/getting men to use condoms for every sexual encounter and getting tested if they’re sexually active.

Also, basic safety: sadly, violence against trans women often comes from romantic or sexual partners. If you are meeting someone for the first time, try and meet somewhere public, or at the very least tell a friend where you are going. I know, I know – the “I’m off to have sex if I don’t text later call the police” message is a buzzkill, and I know we’ve all ignored this advice, but I’m trying to be my highest self here.


Be yourself. Gender dysphoria is a bitch and makes us question ourselves a lot. When I decided to start dating I was worried that my facial hair shadow and my voice were still too ‘male’ and I would be rejected for not being feminine enough. Actually, that’s a loser’s game, and if you want to date someone he should be willing to accept you as you are. Dating and being trans is hard enough without trying to be somebody else.