When to Tell (and When Not To)

A friend of mine posed this scenario to me:

Some man, whom you do not know, walks up and engages in conversation. At some point he asks you out for a movie or drinks or dinner.


Would you, during the date, tell him that you are a transwoman?
Would you bring up the subject even if he never did?
And if so, what would your approach be?

This is a really tough issue that I was struggling over very recently.

The consensus, if you're pre-op, is to let them know up front. But I am not (or am going to try not to), tell everyone I meet I'm a trans woman. When they get to know me better as friends, then I might bring it up.

The reason this was bothering me is that there is a really sweet older guy that works at the 7/11 catty corner across the street from my place. At first, when I moved in to my apartment in September, he flirted with me, loving my smile. As I came in every two weeks for breakfast after filling up he would literally quake with anticipation. At first, I wrote this off as him just being a big tease with all the ladies.

Then he walked over to me at the coffee station and said "Hi," using my name. He loves to touch my hand at the checkout and I love it, too. I decided to stop by for breakfast every morning, because he got such a thrill out of it, and he went to the respectful effort to at least memorize my name. And I got a thrill out of his thrill.

He started paying for my breakfast at the register, not every day, but 3 times now. At that point I knew he had a serious crush on me. I knew it was time to say something, get it out of the way, and let him move on to someone else. But there was never an alone moment I could tell him, let alone figure out how to tell him.

I tried dropping subtle hints that gradually lost their subtlety. I told him that I may not be everything he's expecting. I told him it must be the coffee he was drinking that gave him the shakes. I even stopped by for a stamp last week and said I was so excited that I got the letter I was waiting on, so my passport wouldn't be assigned in my birth-assigned gender. The next morning I repeated why I was happy.

Then yesterday my battery died. It took two jumps just to get across the street to 7/11 where I could make my daily encounter. I had grease on my fingers and asked to borrow the waterless hand cleaner. He helped coax some of the last of the gel onto my hands. And then he comped my breakfast again.

While I was waiting outside by my car with the jumper cables dangling out of my hood, he came out and offered to jump my car. He left for a moment and drove up in a silver PT Cruiser, hooked up the cables to his car, while I attached the power lead to mine. When he was done, he wound up my cable and as he was handing them to me, he told me how he thinks about me every day. I laid my hand for a moment on his forearm.

Then he told me how much he wanted to kiss me, but was afraid it was too public. So I leaned in to peck him on the lips. His mouth opened immediately to probe my lips with his tongue. After a couple of seconds, I broke off and started backing away. Instinct was kicking in and it solved my problem of telling him. As I backed up, I told him, "You have to know I don't have the right equipment, yet."

"You don't see me complaining," was followed by a pregnant pause and then the words, "I'm bi."

And I had been sure I was going to break his heart when I told him. On Wednesdays he works the second shift. I'm going to stop by after work today to pick up a Sobe and say, "Hi." And maybe ask if he would like to do coffee or dinner in a nice public setting.

Oh, and by the way, in case you were wondering, I did get a new battery installed at the dealership nearest my apartment.

Hugs,
Sophie