Hi!

(This is something I originally posted someplace else, I hope it doesn't matter)

I know this question has probably been discussed a few times before but I can't help thinking one more time isn't one too many.

I'm rather happy with my life, I just turned 30 and I have everything going for me. Happiness, work, friends, money, family. You know, I have a good life and everything I can ask for, I think. Last year I remember thinking that there wasn't a single thing I'd like to change in my life, it was just the way I wanted it to be. That is a fantastic feeling.
Well, things change. My boyfriend of 5 years and I broke up. It wasn't an ugly breakup or anything, it was just time for us to go our separate ways, but since then I feel something is missing. I really want to share my life with someone, live with someone, have a future with someone.... love someone again. What good are all those things I'm so happy about if I have no one to share them with?
But I am dead scared of dating and I am dead scared of telling someone about my history. I am dead scared to get thrown away as some kind of pseudo-woman who up until a moment ago was good enough but after telling isn't worthy of being part of anyones life.
In most situations I have come to almost forget about... “my history”... since it doesn't play a big part in my life anymore. You see, I write “my history” just so I don't have to write that I am a transsexual. My mouth doesn't want to say that word and my fingers just misspelled it 3 times because every time I think about it, I get this image in my head where I am telling someone I care about and they walk out of my life because of it... And I feel the pain of past rejections over and over and over again.

But damned be she who does not dare to go after the prize in fear of defeat. Recently I've met a few men who I'm starting to get to know better and maybe, hopefully, one of them might turn out to be someone I really want to get close with. Now, meeting someone isn't the problem, meeting the ONE is the problem because I feel handicapped about not being sure how to approach the problem with telling about my history. I've read a few threads that mostly talk about the “if” in telling but my question is about the “how”.
I know that I can't hide my past from a partner forever, I hate having secrets and I feel I have an obligation to be honest. I don't want to feel like I am wasting their time or cause them (or myself) any more emotional distress than I have to. Telling your partner is different than telling a friend because to a partner you are possibly the future, love, sex, marriage and family. I respect their decision to reject me because I might not be what they are looking for but that doesn't mean it isn't emotionally devastating to me.

So if I tell too late, things might get ugly and if I tell too early they don't get a chance to know me. How do you approach this, do you have a way to tell people that seems to work better than others? Do you have any way to sort of “probe” how someone might feel about this sort of thing? Is there a time to tell which is better than others, like before or after kissing/having sex/whatever? Any experience on how to approach this and how to express it in the most favorable way?

I'm not one of those people who can say “if they don't accept me it is their problem” and just move on. Because it is not only their problem, it is my problem too. And it hurts.

OMG Koala. Lots and lots of hugs for you. That is something I always wonder about, like you said, you read about the if but what about the how. I am definitely not a pro at dating by any means, actually my wife of 30yrs was my only girlfriend and it was her that approached me. But none the less I have an opinion as always. Personally I think the thing to do is take plenty of time to develope the relationship without getting intimate. Make sure he knows what kind of caring person you are first. I think this can easily be done by telling him early on that you have been hurt in prior relationships by going to fast in the beginning and you would be more comfortable getting to know each other better. But like you, I do feel it needs to be told prior to having sexual relations. Like I said, I'm not a wiz at any of this, just my thought on the subject.
Hugs,
Marsha