I’ve been asked this on the phone by more than one potential suitor. Sometimes he’s met me, but more often he hasn’t. I’ve decided it’s part of the fantasy he’s creating.
What does he want me to say? The truth — gardening togs? Baggy sweats and warm socks? Flannel nightie and fuzzy slippers? I tried telling the truth and noticed the conversation deflated.
So now I play. “Nothing,” I’ll reply to see his response. There is usually some incredulousness. Sometimes I say, “What do you want me to be wearing?” After he tells me I say, “How did you guess?” I give him what he wants to hear — and imagine. 🙂
A male friend says since most men are visual, they want to imagine you in 
something sexy and slinky. From Victoria’s Secret. My pal says I should respond, “A black lace teddy,” or “a red silk negligee” — as if many women actually lounge around the house alone in such attire. I’m sure some do, as I read Mariah Carey claims to. None of my midlife women friends do.
I think women rarely ask this question of a guy because we don’t really want to hear “sweats” or “shorts and a t-shirt.” If we’re interested in him, most of us, I think, want to imagine the guy in a nice shirt and slacks, well-fitting jeans and polo shirt, silk boxers, or whatever floats your boat. So best not to ask if you don’t want to know the truth.
Have you been asked what you’re wearing? If so, what do you respond? Have you asked a guy what he’s wearing? Why?
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Obviously, there is something wrong with me since I can’t imagine asking that question except possibly to a long term lover who would probably answer quite candidly that she had on her winter night gown. My guess is these “Mr. Smooths” are trying to steer the conversation around to sex to gauge whether they have a chance of getting lucky. I think women should just ignore it and change the direction of the conversation.
I try to be clever and respond “Not a stitch!!” This usually gets a laugh as it is blatantly obvious I’m lying and then the potential for a sexually charged conversation has been defused.
As is so often the case in the early stages of dating dishonesty is the best policy. FYI As I am writing the comment I am wearing my old Chipendales costume (I use to moonlight in college to pay for my tution). Surprised it still fit, but I guess all those sit ups I have been doing have really payed off!
“So, describe to me what you’re wearing” is the stereotypical icebreaker that is a prelude to an erotic phone conversation. Essential skill to have in, say, a long-distance relationship. Or with Tiffany at that 900-number. And me? Lederhosen.
I’m sure you look cute in your Lederhosen!
Good to know from you guys why the conversation is started. And good to know from some of the gals how to focus it on non-sexual topics. I have smart readers!
You mean they say that SERIOUSLY? I thought that was a commonly known joke. The joke is that is what an obscene caller would say.
Wait–I have a cheezier line you can use:
Him: What are you wearing?
You: A great big smile now that you called!