I'd personally do it, but then again, I'm pretty reckless when it comes to these things. The thought, "What if someone gets hurt?" doesn't really enter my mind. If there are enough positives and things feel good, I'd just go with it. I don't pretend I know where things will lead.

But none of that matters in this case because that's just me. If you say you can't accept her as a romantic partner, then that's that. It's not a matter of, "Well if he looks good enough, do it." Your preferences are your preferences. Sure, sexual preferences CAN change, and they can change drastically (it's happened to me), but I don't know if that's even typical. You know yourself best. If you know that nothing is going to change (and if you've lived in Thailand, you probably already know), then you have to be very clear, because like it's already been said, you don't want to give the person any false hope either.

Even if you say you just want to be friends, the "false hope" thing is still an issue. Being very clear about it may still not be enough. Because it totally depends on the person. Some people are really good at "giving up" while others can't help but develop feelings for the other person despite knowing the impossibility of the situation. It's a risk, and if you really want to avoid that possibility, then unfortunately there's nothing you can do but cut all ties.

I feel for you though. There's this myth that foreign guys can get any girl they want in Japan, but that's not even close to the truth. If you're looking for a serious relationship, all I can say is "good luck" because it's certainly not easy (but it's definitely not impossible either). You don't want somebody who's crazy, yet it's not always easy to discern. Those warning signs that would click in your head in your home country that say, "this person is not right in the head" are no longer always present. The subtle cues often get lost when you're dealing with a very different culture and language. Compounded by the fact that most Japanese people are modest and you're not often going to see their "true" self right away.

If you've been there for 5 years, that's a bit different though. But still, it doesn't change the fact that many of the people attracted to foreigners there are strange or downright scary (which is unfortunate, because not everyone else is like that). For example, you could meet one of those people who are only interested in you so that they can have a cute "mixed-race" (???) baby and use it as a status symbol. Avoid, avoid!

I could go on and on, but I'll stop here. I'm actually going back to Japan in a couple of months, and may even be there permanently, so I just felt the urge to post. I wish you luck though.

I would be up-front and honest about it, and say "I am sorry, but this situation does not align with my preferences." I understand what it is like to agonize over sparing someone else's feelings, but the truth is, if she was trying to find acceptance for her life decisions, she should have known better than waiting until you were hooked to break it to you. Cultural differences aside, she had to have known that there was going to be a significant chance that you'd turn her down upon learning this information, and you're well within your rights to do so.

There's no real way to spare her feelings entirely, but I feel you'd be in the right for expressing your preferences, and if you worry about what kind of person that makes you, I'd say don't, because caring enough about her feelings to worry like this says enough.

As with any kind of romantic relationship, rejecting one's advances to keep them as friends is very difficult, and they might keep trying anyway. It's up to you whether or not you are willing to risk this when deciding whether or not to remain friends.

But we met on a dating site where romance is somewhat part of the terms. I can just say I want to meet without romance but she is really just going to agree under the hopes that in time I will “come around”.

You 'll just have to be clear about that not going to happen(she was upfront to you as well, so i think you owe that much to her)
If she keeps hoping then that is her fault, and she is going to hurt herself, that is not your responsibility, but hers.

If you're afraid of coming around or her trying to make you come around, then be clear for yourself and her as well:

you do not want that and else it is end-of-contact between the two of you.

Although you lectured me on terminology I am likely more understanding than you are (and I chose my terminology for specific reasons).

Out of curiosity, what are these reasons? I think most transgender people find it hurtful when you use pronouns that label them by a gender other than what they've chosen for themselves.

Saying that you're "likely more understanding" than Samith and that you used this terminology intentionally seems an awful lot like you're saying "I do understand how hurtful calling a male-to-female transgender person 'he' can be, and that's why I'm doing it" although I think/hope that that's not what you actually mean.

EDIT: Having read your post again it's very clear that you were not willingly causing offense, and you're by no means in the wrong based on the fact that this knowledge changed your feelings toward this person. I just thought your choice of terminology was odd especially coming from someone who understands these issues, and it does seem possible to construe what you're saying as deliberately hurtful even though you don't mean it that way.

Just out of curiosity what do people want in a relationship and why do they need this? A question to everyone, hopefully OP wont mind me asking here :)

Hmmmm. I guess tell her exactly how you feel and see if she wants to try hanging out as friends(if that is something you would want to do yourself). She may accept based on the hope that she may be able to convert you or change your mind like you(or someone) pointed out, so be sure to not accidentally send any signals and be very clear in your intentions.

That being said, people can change and she may be someone you could be very happy with. Most people aren't very comfortable with the idea of being with a transgender person and that is to be expected, sexuality is one of the most conservative areas for many people for obvious reasons, and the idea of a transgender person is new and unnatural(not necessarily in a bad way though) and most people have little to no exposure to it so it's hard to feel comfortable with. If you do end up hanging out as friends try and be open, it can't hurt because regardless of how open you are that doesn't mean you won't do anything you don't want to, it just means you won't not do something that you do want to do. You might miss out on something great if you aren't.

Just my 2 cents

Just out of curiosity what do people want in a relationship and why do they need this? A question to everyone, hopefully OP wont mind me asking here

Asked my girlfriend that is studying veterinary uni - got simple reply: Each animal has to breed (to duplicate its genetic code in next generation, possibly better adapt to conditions and evolve), so each animal is seeking a partner of opposite sex to breed. It is as simple as this. Humans are no exception. And I also got comment on how children are so ugly and kittens are so beautiful, epic and godlike.

I probably would have stuck with the Yakuza girl

I just hate Yakuza so much. They have no right to exist in this day and age.

Celeb no, because I wouldn't want the fame of dating a celeb

We clearly differ there, since I am on TV for a reason. I’d rather be famous for my own work than famous as the boyfriend of a famous singer, though. Still, she’d be a better match for me than the Yakuza girl. I just don’t really know why I wasn’t really into her, but I can’t argue my gut, even if I don’t know its reasons.

I personally wouldn't even meet her because there is that awkward hope people tend to have that something, anything will eventually lead to a relationship.

Right. Leading her on (even unintentionally) is really harsh and I want to do as little damage as possible while I back away.

Where is your tan dude?

I keep it in my left pocket.

The subtle cues often get lost when you're dealing with a very different culture and language.

After all these disappointments I trudge along by telling myself something similar.

I’m going to miss things I wouldn’t otherwise, but if I just keep trying, not all of them will end up like this. There must be something at the end waiting for me…

For example, you could meet one of those people who are only interested in you so that they can have a cute "mixed-race" (???) baby

I had pretty-much forgotten about this woman but you reminded me that the first woman I met (twice, total) when I came here told me on the second date that she just wanted me to give her a kid. She can’t love men for whatever reason and doesn’t want marriage, but wants a baby, especially a mixed baby.

Am I just a psycho magnet? I didn’t have these kinds of issues in Bangkok…

When they use Google to translate my profile to Japanese, does it turn into, “Do not contact me unless you have serious mental issues or will cause unnecessary epic drama in my life”? Seriously.

she had to have known that there was going to be a significant chance that you'd turn her down upon learning this information

That’s where I sympathize with her. It’s really got to be tough for her to get a match. Again, my troubles times 10. I’m going to try to find the best way to handle this with minimal damage to her, but I will give up if I can’t find a way.

Out of curiosity, what are these reasons?

Everyone wonders at some point what it is like to be the opposite gender.

I entertained the idea about 15 years ago, and my curious nature lead me deeper than most people tend to go.

I really wanted to understand, and as a psychology experiment (and as something of a challenge from my psychology teacher) I even wore a dress to school (no, not the under garments, just the dress).

I entertained the idea long enough to realize firstly that that was just not for me and secondly that I will simply never understand women.

But I got close enough to the metal that:

1. I at least understood and respected women more. I never really disrespected them, but I really appreciated them and their presence more. I noticed the buff guys getting offended at being called a girl and I never understood why. “ME NOT GURL, ME MUSCLES, BREAK YOU!”
2. I can’t understand women but from there on I could definitely understand men who wanted to be women. Except the part where I am heterosexual and they tend to be homosexual. I really don’t get that angle, because to me you have 2 choices: Lie forever or come clean. If you lie you are scum, but if you come clean then the other guy must apparently be okay with that for things to work, which means he apparently must be homosexual, which means you should have just stayed a man. Some of you may be willing to go with a transgender male-to-female without being homosexual, so for clarity I want to repeat that I am talking about something I don’t understand, and it’s just my take on it. In fact I am specifically trying to discuss something I don’t understand so no doubt I’ve got some things off.

So why did I deliberately choose to call her a him?

Because I have been deeper down that road than most and I get it.

I am completely sympathetic, but in real life things are not as simple as, “I want to be called this.”

If I meet her I will of course call her a “her” to her face, because sometimes reality sucks but it doesn’t mean you need to be an ass and hurt people’s feelings.

But on here, we are in reality and there is no need to cater to anyone’s feelings but each other’s, and the reality (which sucks for them, and I get it) is that their genders were determined in the womb after the sudden rush of hormones gave them a gender (or rather took away their female-ness). Surgery changes appearances and preferences change nothing. Otherwise I would have said, “her transition to a female”. Doesn’t make much sense, does it?

Without any knowledge of outside pressure on a certain issue I default to catering to myself, and that means in this case to call her what she actually is (not out of disrespect).

You will notice I have since been referring to her as “her”, since I have realized there is some pressure to do so and because it is not a major deal for me. After being so close to the metal nothing will change my mind internally, but I am fine with changing my language.

Each animal has to breed (to duplicate its genetic code in next generation, possibly better adapt to conditions and evolve), so each animal is seeking a partner of opposite sex to breed. It is as simple as this.

While that is correct, it’s from the wrong end.

We look at the animals that exist today and make this conclusion because it is the one and only thing all creatures have in common, but there is a fairly obvious reason for that.

Any species that does not have some kind of motivation to continue itself as a species will invariably die out. No exceptions.

It follows then that all existing species today (not even just on Earth but anywhere in the universe) by definition are alive because they have some motivation to survive (reproduce etc.)

It’s exactly the opposite to say that we are alive to breed. It’s our built-in desire to breed that is the reason we are alive. No species without self-preservation and a desire to reproduce has ever continued as a species.

Then again, that’s just fancy talk for, “You and me baby ain’t nothin’ but mammals so let’s do it like they do on The Discovery Channel.”

L. Spiro

People go on dating sites to meet Mr. Right or maybe Mr. Right Now. If you're not willing to be either of those for her, you're not doing her any favors by trying to be Mr. Let's Hang Out and Play Video Games. The time you'd be hanging out is time she could spend looking for her "soul mate" or whatever she's looking for. Your plan sounds like the way to go, find a way to let her down easy and move on. People don't form connections for all sorts of reasons on dating sites. She probably will move on just as quickly as you.

Just out of curiosity what do people want in a relationship and why do they need this? A question to everyone, hopefully OP wont mind me asking here

Im my opinion, normal relationships just happen. There is no needing or wanting in general towards relationships, only towards a particular person, if there's any.