Cringe.... So at a New Years Eve party I had met this amazing girl and thought that she was funny, and beautiful, and and yeah you get the picture. I went to a Super Bowl party last night at the same place, a friends appartment, and she's there again. We joke, we talk, I flirt with her over a phone app game that uses "monkey money" for upgrades.... Did I mention hat she's cute? Like, so perfect so far I'd pretend to be a man for a while longer just to spend that time to get to know her cute and awesome to be around. But if she could accept me as I am that would be so worth it. Like I hit the lottery worth it.

Anywho.... So I was there in boy mode because I haven't zapped away enough beard or grown my hair out enough that I want start presenting yet. I'm fairly certain the host who knows didn't inform her of my status either. My status also includes that I have a part time custody of a two year old and I am being divorced by my wife. Busy I know but it's been almost a year since the wife checked the I'm going to divorce you box in our discussions.

The questions:
1. Whoa when does one bring it up that one is transgender?
2. How does one bring it up? Like this is not an aside from a funny joke thing so how does one broach the topic?
3. Good lord I've never been so tickled in my life. How to remain calm on HRT when someone asked you out that you actually like?

I realize that these probably have answers here and that these are probably more of personal questions that should be worked out for myself. BUT I do need a place to put them down outside of my own mind to work out and company on this path is so welcome. Opinions and shared experiences please ladies.

Hoo boy - I see trouble ahead. And why do we always meet people when we are in difficult circumstances? I don't understand how fate makes that work 

Anyway, I would maybe see her another time or two to see if there is a connection, and then you must gently let her know. Its not fair to either of you to proceed when you've got this great big change going on in your life.

You could tell her that you see her as an amazingly interesting person that you would like to get to know better, and maybe if romance is out of the question you would value her company as a good friend. Good friends is a great starting point to slowly work on a romance   

Emily, I am getting the butterfly's as you put it. So I do intend to at least see where this goes. Good friends with no romance is a possibility that I am prepared for. This has happened in the past with other relationships before admitting to being transgender and those ended well and became supportive friendships that I still have today.

Eva, thanks. I'm planning on just that one step at a time. Just needed to get past those initial "oh my gosh" feelings. I am curious but also cautious. I believe that she is pro LGBT but we will see where that goes.

Dinner at 7 downtown at a quiet restaurant. I intend to not bring it up on the first date and instead focus on the basic relationship and what value is there. I want us both to have a chance to put a value on it before dropping the truth bomb as it were. That way there's a fair chance for both of us. I realize that she may be worried about what her friends and family will think if things go well and she talks me up as something great only to find out that it's something she find horribly embarrassing. But I also see that people don't wear signs with a complete stereotype and for all I know she has her own secrets as well. The risk is mutual as it is with any relationship at its beginning.

Wish me luck.

"Rip the Band-aid" so to speak and just explain your concerns. If you want a fair relationship honesty is the best way for feelings to not get hurt. No reason to pretend to be something you're not to hang out. Also as a prospective special friend of sorts I would first be way more concerned about the still married thing. Thats just asking for the drama llama party.

I don't know ,but it seems to me it would only be fair to get it out as soon as possible. What your going through with transition I guessing that you have no intension to stop the process. You've already made that commitment to your self.  If you were in your true identity and she approached you I still believe the same to be true . Just to speak for my self , we're all looking for some one. I'm a lone and always watch out. For me each chance is a possible future. I'm sure she's not in the one night mode. Why force her into that kind of conflict by not letting her  see who you are and springing it on her after she's developed some deeper hope. I just believe to be open from the start is best.

Honesty.

Do you want to take a chance that she might even be ok with you being transgender and want to transition. Then to find out that being you held back this information she feels lied to and she can not trust you and end things.

You said that YOU want to see where it will go, but also she is feeling maybe she wishes more.

You truly need to be honest with her from the start unless you stuff it back in the closet but we all know how that will end in the long term.

Lots of luck, if this is going to be a true match you need to be honest with yourself and her.

Hugs
Isabell

You could always go dressed in prettiest outfit. If she stays she's a keeper

I dunno I mean its a date. I wouldn't overthink it. See where it goes; if it becomes more physical in terms of attraction then do the big reveal (probably before the first kiss.) you are both adults and neither are going to be left heartbroken by it. It might work out well in fact. At the very least even if she gets hung up on you transitioning, she might turn out to be a decent person and friend to hang out with.

I tried that....Ahhhhhhhhhhhh! Run.

An update: it's just a date.

I talked to the my friend, the host from the party who invited her, and it turns out that this girl is going through some similar things in her life.

As it turns out we are both going through divorce.
I am transgender and pan/bi sexual whatever.
She is open to new preferences.

All friends including the my friends here, the host, and my guy friends are all saying don't do it. So it's just a date. I will broach the subject of where I am in life to see if she wants to talk about things. I'm seeking a friendship. I'll keep you updated on how successful I am in making a friend and keeping it from flying out of control.

You're thinking in guy mode. Be careful. I was set up with someone just as I was starting my first round of HRT. A few weeks later, after hiking with friends, dinners, and a movie I finally told her. She got the thousand yard stare, laughed a bit, then started crying. I was devastated. I hurt her. Hours later, back in my own bed, I called her and through my own tears said I'd stop hormones for her. We're now best friends and see each other for dinners, movies, and hikes. It's at times difficult because I think what if...Anyway, be careful. Transitioning is difficult enough without worrying about hurting a loved one.

I'm on month 9 and will remain alone until after SRS.

I deal with this oftenly and have 0 answers...

Seriously. I am not and never will be out at my current job! And I have a lot.. of girls get really into me. Some married, so I just remind their sort of eye candy.. but then we gather this collection.. Mostly of younger girls and then they start getting into me. This is excluding all the women around that get all blushy and giggly around me.

Yup.  You're definitely approaching this in guy mode.  Casual dating is usually much easier for men than for women.  It sounds to me like you two have already had a few good conversations, and you've spent enough time together to know that you'd like more.  And the fact that she asked you out shows that she sees potential in you (a guy), and she probably has more butterflies than you do.

So I wouldn't start off the date with your news, but I wouldn't end the date without it either.

Good luck!!  Make sure to let us know how it goes.