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I have a question.

The other day I was shopping in our big box grocery store. I came to the end of an aisle and there was this tall blond in stilettos. To be honest, all I saw at first were her shoes and that she was as tall as I was.

Anyways, I really wanted to ask her where she got the shoes. But I didn't want to come off creepy.

It gets better. She kept her head down so her hair kind of hid her face. I realized that she was a he. Not sure if she was a crossdresser or transitioning or what.

It was the first time I have seen someone my height (over six feet) in person dressed.

I really wanted to talk to her, but, like I said, didn't want to come off creepy.

Would you be creeped out if a guy came up to you and asked you about your shoes?

Only if his tongue was hanging out, and he was rubbing himself...LOL.

My point is, it depends on how the situation is approached. A nice complement, followed by a question of where they were bought is reasonable.

If the question was, "can I try them on?" I'd giggle first then ask his size. Kara, you didn't say what you would do or if it would creep you out. When I have been approached by strangers, they have always been to tell me they like something they see. Hard to get creeped out by a compliment. I'm not going to be creeped until there is more than the look of the other person -- male or female.

If you see your manazon again, maybe you need to smile and simply start with, "love those shoes" or whatever catches your eye to start the conversation. BTW, complimenting on the boldness of heels with height ain't bad either. Tall teens will wear tall heels so why can't other girls?

Yes, reasonable compliments are good. But if you want to open the possibility of a conversation you have to also try an open-ended conversation ploy, and offer your confidence.

"Great shoes! Can I ask where you got them? I don't have any quite that nice."

Starts with a compliment and continues with a natural question that only another woman or a trans-person or CD might ask. And then you signify that you too have concerns about women's clothing. This mildly outs you to her, but it also and more importantly offers her your confidence in a possibly shared interest, which is the fastest way of gaining her confidence in you.

It's an old con-man maxim that to gain someone else's confidence, you offer them yours. (Hence the name "con-man" and confidence trickster.) Of course, you are not about to use this information against her or to your own advantage. It's simply a means of breaking the ice and possibly gaining an interesting acquaintance.

It's worth trying, next time the opportunity presents itself.

Paulette wrote: "Great shoes! Can I ask where you got them? I don't have any quite that nice."

I'd be careful taking that approach. The person may not be trans and could find your outing yourself kinda creepy. The person may not be trans and take offense that you think she looks like a man.

The person may be trans and may be made to feel bad about not passing.

Keep it simple and about the shoes, not about the gender.

I have complimented GG's many times on what they were wearing or a specific item. Some times I will ask where they got them. But sadly usually is usually a year or more that they got them.

I would say just keep it simple and say something like nice top. If they pause to make small talk you can ask where they got it.

Unless you've just come from, or going to, some other meeting or event, dressing more formal than a grocery store fashion calls for is asking to be looked at. It's been a few years now, but there have been times I had to stop for a few last minute items on the way to a party. A few looks and smiles are expected. A 'nice shoes' or 'like your outfit' comment usually came from women. Men making such comments puts a lady on the defensive. It's all in body language and voice inflection. A man can compliment a lady on her looks and not make it seem like a come on line. In which case, the compliment is greatly appreciated.

And thanks so much for reminding me that I haven't had such compliments in quite some time

Eileen

Thanks for the replies.

I will keep your advice in mind if the situation arises again.

Kara