Should I wear heels even if I am taller than my date?

Oh god no. Men are really weird about height.

No.
You date a lot.

No, go with flats.

But remember you are both the exact same height when you are lying down,

Why not get it over with as soon as possible

Yes. You need to establish dominance over the male.

Yes. If he’s that insecure about the difference in height then you know not to date him again.

If he’s going to get upset about you being taller than him, you might as well find out sooner rather than later. Do you want to have to wear flat shoes whenever you’re with him? I like to wear high heels so a guy who got antsy about me appearing taller than him wouldn’t work.

Yes, you should.

“I’m 5’9 and my date is 5’8.”

For one thing, apparently he already knows that you’re taller than him.

Besides, a well-adjusted runt will have his own pair of even-higher heels for those special occasions. ;-)

If you like heels and you want to wear them, then yes, why not? I’m also 5’9’’ and have always had huge issues when it comes to being taller than guys and I’ve never worn heels because of it. The older I get, the more idiotic it seems. You shouldn’t feel responsible for the insecurity a lot of men have when all you’re doing is being yourself.

So I completely agree with @Earthbound_Misfit – if he has a problem with you in heels, it’s a lot better to find out sooner rather than later.

@dopeguru Unless he’s blind, he already knows he is shorter than you. He’s comfortable enough in his own skin to ask you out, he’s probably okay with heels. Most secure guys don’t sweat the physical stuff like height. You’ve dated a lot of bad boys, maybe give this guy a chance. And if you’re still unsure, maybe you could ask him which shoes he prefers. It’s a little forward on a first date but it might break the ice and give you a read on the guy.

@Adirondackwannabe, why should she take into account which shoes he prefers? If she wants to wear heels, she should. If she wants to wear flats, she should wear flats. His preference is irrelevant.

I agree you’d assume he already knows he’s shorter than her, and there’s no evidence to suggest he might feel intimidated by her towering over him in her heels. If he does get upset about it, she’ll know he’s an idiot and she can be busy next time he calls. Some men would find her height sexy I’d imagine.

@Earthbound_Misfit She shouldn’t take it into account, but I thought that might be a way for her to feel more confident in her choice. She’s not overloaded with confidence.

This young woman needs to learn to be assertive and to enjoy owning her own choices. What she wears is her choice and should be her choice and she should not ask a man for their preference or permission. If he gets upset about it, it says a lot about him.

@Earthbound_Misfit Whoa easy, I wasn’t going into Man is right Women does what Man says at all. I’m thinking we start with small steps in the assertive direction and trying to help her. Remind me not to cross you. :)

How is suggesting she gets his okay to wear a pair of shoe encouraging assertiveness? I’m not even slightly cranky with you @Adirondackwannabe, but I totally disagree with any suggestion that she should seek his approval to wear clothing.

No.

@Earthbound_Misfit Reread the last half of my last sentence.

I did read that @Adirondackwannabe, and I still don’t see how asking his preference is taking a small step towards being assertive. We’re talking about wearing a pair of shoes here. Really, how is a woman checking whether a man likes her shoe choice assertive? Do you really believe that?

She either hears he likes the heels, and she’s confident going with them, or she hears flats, and she knows he’s insecure. She can take it from there. Small steps.

Why does it matter what he prefers @Adirondackwannabe?

They’re her shoes. She’s wearing them.

They’re her shoes, @Earthbound_Misfit.

Where did the OP imply a preference for heels?
Dating common courtesy is now weakness?

Cripes. If your not worried about the impression you give on a first date, shouldn’t you give it up?

Eh…

Just wear whatever you want to. If you’re worried about it bothering him, ask him. If it bothers him… then choose whether or not you want to never wear heels around him for his sake, or if you would rather find someone who accepts you and your fashion choices, do that – though I do suggest the latter if he turns out to be that insecure.

@DrasticDreamer

“I’m also 5’9’’ and have always had huge issues when it comes to being taller than guys….”

What if a guy found you especially attractive because you were taller than him?

@Nobody_in_particular

If I woman is taller than the guy, guess what’s closer to his eye level? ;-o

@Brian1946 That would be awesome, but unfortunately, it’s really rare in my experience. I even grew up with other females saying, “Yeah… it would suck to be that tall. I definitely wouldn’t wanna be that tall.” :-/

Not if it’s the same guy you have been throwing fits about for months. If so, stay home or have a girls night out in whatever show fashion you wish.

@anniereborn: If this is a first date she is asking about, it’s probably not the same guy she’s been going out with for months.

@jca You would think that, wouldn’t you? But if you read back to one of her latest posts it said that all her other posts before that were collectively one guy. (which they weren’t worded that way either)

@DrasticDreamer I’ve always found tall women attractive. It’s always been weird to me that people get so worked up over the idea that a man has to be taller than the woman in a relationship. The concept is just bizarre.

@DrasticDreamer @gorillapaws

Me too.

Actually, the more physically superior to me a woman is, the more attractive she is to me.

My wife is 2 inches taller than I am. When we were married the photographer tried to get me to stand on a stool. Both of us said, “Why? She’s taller than me?”