I was over at an MF, and we got to talking about guys who are “bad at dating.”
“It’s usually the little things, like as small as just telling you where they plan to take you on a first date. It doesn’t matter if you’re going to a lounge, but if you’re not, it really does! I can’t count how many times I walked around Central Park in 3-inch heels. And I went bowling in heels, too.”
“They let you bowl in heels?”
“I don’t remember if they let, exactly. But I wasn’t going to put my feet in those bowling shoes without socks! That’s disgusting! If I’d have known I’d have brought a pair. And I would have gone ice skating in my heels too if it was possible. I mean, seriously. Why am I handing in a pair of 4-inch stilettos at the skate rental? That’s just weird! There’s something wrong with that situation. And then me trying to skate in a fit-and-flair dress that I bought for sitting in a lounge looking pretty. If you’re going to do something unusual, you tell the girl.”
This rant, mind you, from someone who’s been married four years. I guess her bunions still remember.
Bad for Shidduchim 
I don’t understand. If the guy’s driving somewhere, and you ask him where you’re going for the date, and he says “Oh, I thought it would be nice if we went bowling”, why don’t you speak up and tell him that you’re wearing heels and bowling won’t work?
How about not wearing heels if you don’t know where you are going? Seems like common sense to me. I’m not sure why the female dating population has this obsession with wearing high heels all the time. Anyone care to explain it?
How about knowing where you’re going because you discussed it with him beforehand?
I don’t own dressy flats.
Not because I’m dating. Because I have a mirror.
Not everybody does a pre-date phone call, mir119.
I wear teva sandals to my dates. No wonder I’m still single.
Whenever I go on a date I let the girl, or at least the shadchan (if there is one), know the type of activity we’re going on. I won’t necessarily say, walk, lounge, ice skating, bowling, etc. but I’ll give them an idea about how casual/dressy to dress and what sort of shoes to wear. I think it’s insensitive not to.
If you don’t do a pre-date phone call, you can hardly complain about the fact that you don’t know what you will be doing on the date.
Not true. I’ve had guys tell the shadchan to relay the plans when they involved, say, dinner or walking. See Lost and Found’s comment as an example. 🙂
Suds, I let my friends dress me for my first two dates with my husband, which resulted in a nice but somewhat non-normal Mindy look. Third date, I wore my usual sandals and long cotton skirt, to my friends’ immense horror.
Anyway, I think both parties should look nice on a date, but formality is relative to the culture.