Sometimes, especially when it comes to dating, it seems like life was a lot easier as a really attractive lesbian than a decent looking guy. I've mostly been in relationships, but before I transitioned, flirting was so easy. I was good at it. Now I've turned into the awkward guy that stares at his shoes because I just don't know how women will react to a transguy. Can you guys relate?

yes and no. i have always been decent looking... but i have also always been the one to stare at their shoes or freeze up. but you know what they say, confidence is key.

I have always sucked at flirting.  And I usually don't notice when someone is flirting with me.  I am just too dang friendly and assume that anyone else being friendly is totally platonic.  This is why I try and go with the upfront approach of just asking someone I like out instead of spending too much time doing more subtle stuff.  I talk to EVERYBODY (including strangers) like they are my best bud, so apparently half the world thinks I am flirting all the time anyway, especially since I tend to compliment the crap out of people.  I actually find it easier to flirt with girls as a trans guy, though, because I was never an intimate member of the lesbian community despite being bisexual so I rarely saw people I knew for sure liked girls.  Now that I consider myself male, I know it is much more likely that the chick I am talking to will have an interest in me if I ask her out and so I feel more free to flirt.  Seems kind of backward, but that's how I feel about it despite my "trans" label. 

Mmm, kind of. At least early on. It was very difficult for me to flip that switch from lesbian to man. Especially since I had been fairly involved in the gay community prior to coming out, it was difficult to reconcile that I now identified differently and was asking people to recognize me differently.

I think it takes some time to get back into flirting. I'm much more comfortable with it now.

I never was really a flirt and that hasn't changed since transition. I can start a simple conversation and get good feedback. If you really like someone and they like you it be easy to tell and would be mutual. I don't know if this makes sense...I'm just not a natural flirt. I'm always polite and genuine.

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I could never flirt to begin with. A close female friend of mine spoke to me the other day about how many times she's flirted with me and I haven't even noticed. I don't know, after living as a 'female' for so long I just find it very hard to believe that a girl would flirt with me, and I write it off as just a friendly gesture as I experienced girls being close to me for so long, doing things they typically wouldn't do to guys, as I was once seen as a girl. As for flirting with others, I'm not confident or comfortable enough to even try that yet lol. My voice dysphoria is too much for me to talk romantically.

I never came out as a lesbian but I assume most people saw me as one as I have never once showed interest in guys, am not into much of anything feminine and especially after my haircut. A lot of people still don't know I am trans.

Can I just ask if the women you previously flirted with were lesbians too? And are the women you are flirting with now straight? I ask because I suspect that women with different sexual orientations respond to flirtation differently and that could be contributing towards to discomfort you are feeling...?

Well you might try to relax.

If you look around you will see flirting has not necessarily something to do with good looks.
People with all kind of looks flirt.

Its just like saying hey ... I'm here ... how are you ... lets talk a bit ...

It just takes being intersted in the other, asking a few questions, and listening ...
giving a few remarks from time to time...

I'd say don't be too shy or too timid ... just be yourself and talk to people.


*hugs*

Being trans can make some interactions awkward, but 90% of those interactions involve you not wearing any pants. There's a whole lot of space in between "Cute earrings" and "Let's go somewhere more private" where your trans status isn't relevant at all. And if you can't navigate that space, you won't even get to the point where you have to worry about how she'll react when you disclose.

So don't get too far ahead of yourself. Don't look at a cute stranger and start imagining an awkward conversation about your transness. Talk to her first. Wait until you really hit it off with someone before you start thinking about how she'll react to your body.

That way, you're thinking about a real, concrete, multidimensional human being. And in my experience, those are both a lot more interesting and a lot less scary than imaginary people. (Granted, my experience is with men, but women are people too.)

Quote from: transiconoclast on March 21, 2016, 07:56:53 AM
Being trans can make some interactions awkward, but 90% of those interactions involve you not wearing any pants. There's a whole lot of space in between "Cute earrings" and "Let's go somewhere more private" where your trans status isn't relevant at all. And if you can't navigate that space, you won't even get to the point where you have to worry about how she'll react when you disclose.

So don't get too far ahead of yourself. Don't look at a cute stranger and start imagining an awkward conversation about your transness. Talk to her first. Wait until you really hit it off with someone before you start thinking about how she'll react to your body.

That way, you're thinking about a real, concrete, multidimensional human being. And in my experience, those are both a lot more interesting and a lot less scary than imaginary people. (Granted, my experience is with men, but women are people too.)

transiconoclast,

Welcome to Susan's,

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With warmth,

Joanna