Social Question

Crossroadsgrl's avatar

If you're a 35 year old male, what do you want me to wear on our date?

Asked by Crossroadsgrl (925points) January 2nd, 2011

okay that’s not really the question, here it is:
i’ve asked this 10 diff ways but I have 3 weeks or so and love the ideas here:
You’re 35, MALE, single, met me briefly, and yes, there was an attraction. It’s been several months since you’ve seen me and I’m walking into your office today to casually ask you out ( for sometime later… )
To up my odds, what am I WEARING??
I know this varies with each man on the board and please, I’m not looking for skanky waste our time answers :) I’m a normal, friendly :) and a few years older than him woman,( but look and act HIS age ;)
Looking mainly for men to answer although either is fine, because honestly, I CAN dress myself, and in the end will know what to do, but wanted to see if something gets mentioned several times. Men have fantastic thoughts about women and clothing. thanks !! :)

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23 Answers

rooeytoo's avatar

I think you should be wearing whatever you are comfortable wearing. Don’t pretend to be something you are not, just be the real you, if that isn’t enough, then he isn’t worth the effort.

Good luck, you are gutsy woman!

(Just in case you didn’t know, I am a 66 year old female, not a 35 year old male which probably makes my answer and perspective a lot different)

Crossroadsgrl's avatar

thank you , yes :), I absolutely will be comfortable and not pretend lol….just looking for fashion forward male thinkers I guess….entertaining my creative mind while giving it a few weeks to go in…jeans? dress? very normal? slightly edgy?
I enjoy each of these and again, am just having fun “preparing myself” ...keeps my nerves down.

ZEPHYRA's avatar

Whatever is YOU!

Deja_vu's avatar

I’m sure a burlap sack would do. Don’t over think it.

jazmina88's avatar

show your assets

ucme's avatar

Clothes…...at first! ;¬}

Deja_vu's avatar

or Hot pants and roller skates. just saying

Pandora's avatar

I’m not a guy, but if I was you, I would wear a white form fitting blouse (not see through or anything like that) that looks very sophistcated so he can see you when your coming over and a pencil skirt, so he can see you when you are going.
When I was younger, that combo always seemed to turn heads.

Adirondackwannabe's avatar

@Pandora You hit that one out of the park. 49 year old male setting here imagining that and wishing it were me. :)

Summum's avatar

If I were the guy I would love to see you dress modestly and with something very attractive. For instance, if your eyes are green then wear something that enhances your eyes. That is one of the first things that attracks some men. I think the eyes are the windows to the soul and say alot. Also very light makeup. I enjoy a woman being more herself than so much makeup you can’t really know what she looks like. And dress more like a woman not that a T shirt and levis is bad but first impressions are big.

Scooby's avatar

Smart but casual, no formal wear like trouser suits… jeans & a nice knitted top & a parker if it’s cold! :-/
Oh yeah, I’m 43 maybe too old for this question!!! ;-(

wundayatta's avatar

I think you don’t want anything that distracts from your message. You want me to focus on your face. So don’t wear anything that obviously calls attention to your boobs of your legs. Other than that, anything professional is fine. It’s your message that would shock me. I’m married, but even before I got married, no one ever asked me out.

If you wear a low cut blouse or a tight sweater or something that shows enough of your thighs, then I’m going to think you are interested in something other than I believe you want.

You want to grab me with your eyes. They should be mischievous and playful and sparkling. You’re doing this with a devil-may-care attitude, just for fun. You want to challenge my sense of fun and intelligence, and make me feel like you know something I don’t. This way, I’ll rise to the challenge as well as the novelty of being asked out.

Me 54 fwiw.

bob_'s avatar

What kind of date are we talking about?

crazyivan's avatar

Obviously the location of the date coms into play, but wear something that says that you are flirty but not easy. Wear something that calls attention to your “assets” but doesn’t show much of them. Sexy without slutty is actually pretty hard to pull off so I would go for something that shows your curves and leave it at that.

I agree that anything overly “proffesional” sends the wrong message.

Best of luck.

Dutchess_III's avatar

@bob_ Actually, she’s talking about walking into his office TO ask him out on a date. I think.

stevenb's avatar

I imagine you showing up in whatever color best suits you, makes you very comfy and confident. Wear a little black dress if that is what does it for you, or a pair of nice pants and a nice shirt if that is your best outfit. I would be looking at your eyes, lips, face and hair mostly, so play up all of those. Go a bit light on the makeup, but make sure to draw attention there, using good color in eye shadow an liner to make them pop. Glossy lip gloss is always sexy and inviting, a little subtle glitter or shimmer on the face is always pretty, but I don’t mean 12 year old glitter. Lol. Fix your hair in your favorite style and go rock his world. If you are confident, sexy will come through all on it’s own. Best of luck to you. Oh, shoes to. Wear mid height heels if you like those. Something cute and sexy.

Crossroadsgrl's avatar

oh wow, you guys are PERFECT !! thanks SO much this is all unbelievably helpful, I hadn’t thought of HALF of it !
love yall !!!

Crossroadsgrl's avatar

so I look similar to Ashley Judd, I guess very very similar, so that gives you a pretty good idea.
except my eyes are brown, and maybe hers are green, not sure.
so that’s what I’m working with lol…think I may TRY the pencil skirt nice white blouse thing, with some cute heels. I love heels and wear them like tennis shoes
my hair is….lol..well free spirited like my personality, so it will I guess be half up half down and somewhat messy looking but fixed into whatever it does that day
oh goodness, this is getting me very very nervous
someone mentioned that confidence = sexy but isn’t OKAY if I’m of course somewhat nervous walking in?
or NOT. ? I tend to laugh more when nervous I’ve GOT to find a way to chill myself out.

**what’s the FIRST sentence after “Hi !! ” cause I’m going to want to give him a hug but I can’t : / **

The thing is…if I can get him to just GO, to take a CHANCE, I believe that would be it. We seem to have everything in common and he’s SUCH a sweet man.
Anyway, thanks again these are very helpful ideas.

Adirondackwannabe's avatar

@Crossroadsgrl Go for honest, and not too over the top. You want to hug him, but you’re in a business environment, so tell him that in your own words. Maybe you’d like to give him a hug, but not in the office. How about we go to….. Keep it simple and from the heart. Good luck.

Crossroadsgrl's avatar

How many people are going to sigh with disappointment if I can’t make this work ?
! Lol
:0
None, I know ;)

stevenb's avatar

Don’t worry, it’ll work for you and be great. Best of luck!

Dutchess_III's avatar

Let us know!!

Crossroadsgrl's avatar

I definitely will…it’s going to be several weeks, as strange as this sounds.
( I like to think/plan WAY ahead what can I say )

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