At work I am completely stealth. And tonight I asked one of my coworkers out on a date and she said yes. I'm not sure if anything will become of it, but I was wondering at what point if things were to go well should I tell her that I'm trans?
Anytime I have dated they've known so this is the first time where she doesn't know and well none of my coworkers know so I was wondering what anyone else does or thinks about it.

Thanks in advance.

Right away.  Yanking the chain of someone who wan't going to be into it anyway is a waste of both of your times.

Don't wait until your wedding day? JK

I told mine BEFORE he asked me out. It prevents lies and danger in the long run. I mean, how can you start a relationship if it is built on deception?

It's not right to be shaming people who aren't comfortable talking about their past with people they are dating by saying they are lying and basing their relationship on deception.  What you do in terms of how you live isn't always right for everyone else.  Not everyone is able to be out and proud.  Its great if you are, but come on, you are not lying or deceiving the person by not telling them every thing about your past.  This thread has been done so many times and it often leads to bad feelings between members who have differing view points.  You can't go around telling people what's best to do if you haven't lived in their shoes. 

The answer is, do what feels right for you.

You are right Caysee, but that is what we are here for, to give ALL opinions for the person to use to make decisions. I don't condemn or judge, just provide input for others to use. If we all thought the same, why would we be here? If they use what I provide, OK. If they choose not to, OK. As long as people ask I will provide input as well as I can.

I'm all for stealth.  But dating co-workers is another matter altogether.  As the old saying goes, "don't poop where you eat!"

If you wish to remain stealth at work, it is risky to tell her. Worst case scenario she may potentially tell everyone else. You probably shouldn't tell her until you fully trust her.

Yeah it is risky, but tell her when you feel comfortable around her and I would normaly tell after a 1st or 2nd date pending how it went. I tried dating girls but I told them before I ask them out and it all didn't work out. 

Quote from: katiej on February 23, 2014, 11:57:02 PM
I'm all for stealth.  But dating co-workers is another matter altogether.  As the old saying goes, "don't poop where you eat!"

^^This.

But what we would or wouldn't do in your situation doesn't matter that much; however, keep in mind that you did ask for opinions.

That being said, the others are right.  Whatever feels right for you - but just weigh the pros and cons of either scenario.  For example:

Telling her right away:

Possible pros - clear the air so she has no unrealistic expectations that you can't fulfill, allow her to accept or reject you without feeling (potentially) guilty of not being forthcoming, etc.

Possible cons - she changes her mind and you feel rejected, if she does or doesn't reject you she may out you to other co-workers

Waiting to tell her:

Possible pros - you have time to build a friendship and you can trust her, she sees you as a man first (though that's not to say she wouldn't even if you told her), etc.

Possible cons - the longer you're together and if you tell her and she rejects you the more likely it is that you'll be pretty broken up about it, you may feel guilty about not being forthcoming, she feels deceived that you didn't tell her straight away

These are just examples of things that "could" happen.  Use your own discretion.  You have to live with the choice, either way.

I'm stealth and personally I'm not a fan of saying something ahead of time, but thats just me and I know people disagree. Many straight cis people view dating a trans person as dating a person of the sex assigned a birth, unless of course they are familiar with trans and how we really are. Unfortunate but just the way it has been for me and the people I have met.  So reveling right up front that you are trans to a woman there is a decent chance that she will view you as a woman, not as a man. If you wait until she gets to know you a little better she already clearly views you as man so when you tell her that you just weren't born with male parts she will likely be a bit more on board so to speak.  Also, you never know how it might go, after a couple dates before things get intimate you may decide its not going to work out anyways so no need to say anything at all and you can still remain stealth at work. There of course is always the off chance that she's bi or maybe clocked you already without you knowing and very open to dating a transman, you just never know.

Thank you for those of you who responded.
And just to clarify I am fully aware there is no real right or wrong answer to be given to this question. I was merely seeking other's opinions/thoughts to weigh against my own and to use as a way to see if there is a different angle to look at other than the angle I am currently looking at this from, if that makes sense.

I can see and relate to what everyone has been saying even though some opinions are different and that was what I was after in posting this. So thank you for that.