New woman faces awkward dating

Dear Amy: I am a transgendered female. I began my journey six years ago and have successfully come out at work and with friends and family. I am now at a point where my life (socially and professionally) is pretty standard. I have two issues I need help with, Amy: First, I believe the right way to tell a guy about my status is when he’s asked me out, although I’ve had friends tell me to go out with someone once or twice before telling the guy (yikes).

Second, I had a man show interest in me recently at an industry-related event. He astonished me by telling me (out of the blue) that he’s “bi,” but that he likes transfemales best. When he said this to me I felt mortified. I felt objectified.

It felt like he was all about sex first and maybe knowing the person later. Was his timing as awful as it felt, or did I take myself too seriously?

If you can offer any advice on these two matters (or solicit comments from people) I would appreciate it. — Girl On-Hold

Dear Girl: Any time you find yourself thinking “yikes” about a suggestion from others about how you should behave — it’s the yikes-reaction you should pay attention to. I agree that you should be “transparent” with potential dates at the outset — certainly during this phase of your transition. Later on, you might feel differently.

In terms of this man’s behavior toward you, again I think your instincts are right. He chose a professional event to come on to you, and immediately let you know what his sexual preferences are. He didn’t wait to read your potential interest in him.

Some guys are like that. They see a beautiful woman and immediately objectify her, make all sorts of assumptions, and lay it all out there. So no — don’t settle. Someone like that will never appeal to someone like you. Write to Ask Amy, Chicago Tribune, TT500, 435 N. Michigan Ave., Chicago, IL 60611.