Should I Ask An Older Woman Out On A Date? Options

Unusual topic? Maybe. Just curious as to what y'all think.

I can't really tell if she's interested in me or not, and I am 20 - I would guess she is 40 or 45. I can't tell if she would be flattered or merely laugh that a kid would ask her out. I don't mind being laughed at, but I have to see her somewhat often, so it could be awkward. I am immune to humiliation, but I'd rather not make her uncomfortable.

I know no one else knows what I personally "should" do; I just want some other opinions on my prospects. Can a 20-year-old ask a middle-aged woman out on a date? Is it done? Is it socially unacceptable?

I resolved at around age 5 not to have anything to do with people, and so far the only people I've really had to deal with are my professors... so I'm unsure about these things. (IMG:style_emoticons/default/13.gif) (My initial plan was to ask "wanna bang?"... but it has been suggested to me that this is a poor approach.)

This post has been edited by Vilhjalmr: Jun 16 2010, 03:34 AM

Thanks all for the replies.

Personally, I'd recommend just flirting and using your masculine wiles.

you can kinda tell if someone is into you, just gradually escalate the flirting.

Well... I don't really know how to flirt... or use "masculine wiles" :lol. "Would you like me to drop by your house?" is about as subtle as I get. Or maybe I could tell her she's pretty and ask her to coffee at the bookstore near her place. Those are my only ideas so far... (IMG:style_emoticons/default/13.gif)

I'd imagine that there's an interesting story behind that. I'm curious, why?

I think being around people makes me stupid. I have to adopt 'an personification' of a some sort, temporarily squeeze my mind into it and/or block out certain areas, and be bound according to the social forms that I'm allotted by the mass of my surroundings and assume 'identification' with that for practical reasons. In itself, it's a painful procedure that I try to undo with varying success whenever I'm alone, but occasionally bits stick, and possibly become 'neuroses'--by my view of what that means, since popularity is not the determining factor.

I'm sorry to disappoint you, but it's not really very interesting. Happened from 9-12 or so, I guess. I was a trusting child and was rapidly and publically "betrayed" by a succession of friends and crushes. Silly, looking back at it, but I was very hurt and resolved that only books/games/knowledge could be trusted/were worth time. On the whole, I think I made the right decision; I've gotten entangled with relationships once or twice since then anyway, and both times sort of reinforced my determination to be a recluse.

Plus, I like being alone.

I think I do something similar to what you're saying, if I understand you right. When forced to be around people I usually find myself adopting their way of speaking and thinking, knowing it's not me but forcing identification for the time being. Maybe it's a relic of school. Lots of bits from books and other media I like stick to me, which is probably why I'm on this forum now.

What do you call neuroses?

Dude, trust that for any young male of 20 to ask a woman of 40-45, the woman would probably be pinching herself. I don't suggest coming straight out with... wanna bang!! (IMG:style_emoticons/default/laugh.gif) She would probably perceive you as just some randy kid tryna get his shaft wet (IMG:style_emoticons/default/evil.gif)
The best way would be to come across somewhat mature. Ask her if she would like to get a coffee, then start asking questions about her... if you seem generally interested in her she'll be pleased and then the come back to mine if you want line will be eased.

I want to believe that bolded line!

You're probably right - there's both an age and social standing gap between us, so "wanna bang" probably won't work... even if I am extraordinarily handsome... (IMG:style_emoticons/default/lol_2.gif)

Well if you to are wanting to get a real relationship started then i would be upfront and honest about it ask her in private so it spares her the embaresment of it. Then ask her if she would like to see each other in a relationship or would she want to keep it secret and just have a fling. And if not a secret i would not worry about what people think i know how hard that realy is its not an easy thing but if you to really feel the same way about each other then you should not let people's judgment keep you from happiness. I hope this helped you some i know that this is only comeing from a 17 year old kid and you will probably disregard it but this is just my thoughts on what you should do. I hope you find happiness and good luck to you...

I don't even know if I'd prefer a relationship or "fling." I wonder how she would see it. But definitely in private, indeed.