Should I ask this girl out?

Brilliant! I guess her e-mail address might be lastnamef @ big insurance company . com, but that would be a guess.

I don’t know. I should call her cell, late at night (so as not to arouse her suspicions, but hopefully to eventually arouse her, heh heh) and leave a quiet and breathy voice message saying "Hey! Want to get laid by an older guy? Go to double you double you double you dot boards dot straight dope, all one word, dot com, slash ess dee em bee slash (etcetera).

Chicks love that kind of stuff.

Dangit. kicks dirt :frowning:

How about you just plunge in and spill the beans like you’re doing here. Say something like, “I hope this doesn’t come off as creepy and if it does just say so and you’ll never hear from me again but,…[something about seeing if she’s interested in doing something interesting because you got a good vibe from her or something.]”

This way, she’s only a little uncomfortable if she is going to be and she is fully in control of the situation. You might regret asking, but you’ll definitely regret not asking. It would probably help if you could find something you would be mutually interested in before you try though (and if you can’t I wouldn’t bother.)

Some of you are way overthinking this. Just call her and find out.

I think you are allowed to hit on someone way out of your league, but in return you should do someone uglier than you every once in a while so you don’t throw off the delicate cosmic balance.

I completely disagree with starting off by saying “I hope I’m not creepy”. Because then it makes you sound… creepy.

Second call for overanalysing. Just do it!

She can only say no. and then what? You’re old enough ( :stuck_out_tongue: ) to handle rejection.

When I was 22 I met a 36 year old and we had a wonderful relationship for a number of years only ending when I moved cities. I’m sure if I didn’t have to move we’d still be together.

I’m a 24 year old female and another vote for very creepy (sorry). Nothing from your brief interaction suggests anything other than she’s a nice person who was friendly to the guy who found her ID and helped her out. If I were in her position and got a follow-up phone call asking me out I’d worry that you not only knew my number, but my name, where I lived, and where I worked.

I don’t know anyone who would be interested in hanging out with someone they just met, without any indicator that they had interests in common. You didn’t have any meaningful conversation and no matter how you word it she is going to think you are hitting on her. Be the kind stranger who went out of his way to return her ID. Don’t be the sad, middle-aged loser she laughs at with her (20-something) friends.

I think I’m going to have to go with this answer. I had her number written down in two places, and I’ve thrown them both out. I just need to delete it from my caller ID, and Bob’s no longer your skeevy uncle.

Pulling off calling her takes far more self-confidence than I have right now, which is basically zero. As far as “you’ll always regret not having tried”, earlier this year I already beat the hell out of that particular jagged rock with my face. I’m in no mood to torture that rock again any time soon. I tried, and fuck yeah, I regret it even more than if I hadn’t.

I got some cute stranger to think kindly of me for the better part of a day on Wednesday. That’s a victory for me these days. Pathetic? Yep.

Wow, I’m in a really dark place right now.

Well, tdn, if it helps any, I think you’re very cute. I generally try to stay out of threads about your love life, since I’m kind of biased, what with you being my Internet crush and all. But I did look at the one about your personal ad. I liked the first picture (you know, the one everyone thought looked like a serial killer). :slight_smile:
I can’t see why any woman wouldn’t find you attractive. You’re smart, educated, kind, gainfully employed, talented, witty…the whole package, baby!

About this particular situation, I’m kind of torn, but it’s not because you’re too old. It’s because she’s too young. I don’t think a twenty-something girl is ready to appreciate you properly yet. So you’ve decided not to pursue her…fine. However, if you ever do run into her again by accident, I don’t see any reason y’all shouldn’t get to know each other better, and she will be lucky to have that opportunity.

And furthermore… (( tdn ))

Thanks, Dung Beetle! That helps. Now if I could only convince the other 2,999,999,999 women in the world of how right you are. :wink:

A trenchcoat and nothing else. Chicks dig that.

I would wait about two weeks before I called her about anything. One week minimum. This way she’ll have had time to either forget you or long for you. Either way she’ll be better prepared with an answer to your question and you won’t sound desperate or stalky.
Plus, you’ll likely have lost the urge by then… :wink:

Oh, if you do invite her out make it with a group of people and just tell her that you seemed like the kind of person that likes to have fun. You’ll be at such and such place with a couple of friends of mixed company and that you’d like to invite her and suggest that she bring a friend too. If she’s got a man she either won’t go or will bring him and if she’s interested in you she’ll come alone (bonus!) or bring a girl friend.

Didn’t preview,
So, dig that number out of the trash and call her in next weekend!!

Don’t exaggerate, dude. It would have been half an hour, tops.

:stuck_out_tongue:

FWIW tdn I wish I could tell all the women out there the person I’ve gotten to know on this message board. I liked your personality way before I ever saw a pic of you and now that I’ve seen a pic it seems to me like you’ve got the whole package.

Hang in there. Your woman is out there. Just keep your eyes open and don’t forget that you’ve got a bit of a fan club right here on the SDMB.

You are probably wise to ditch the phone # and just let it rest though there’s a part of me that wants you to call her and just take that chance.

Call her and tell her all about how you posted on the internet about her. Then ask her if she wants to go steady.

Thanks, velvetjones. That’s so nice to hear. And it does help.

How I wish I could take you and Dung Beetle out for a nice tall glass of whatever you’re having.

So, tdn, where’s this pic that has all the other girls drooling?

That one’s gone, but I thought this one was better. But last weekend I totally changed my hair. I’m now peach fuzz with a goatee.

Definitely cute! If you were 250 miles closer, I’d be interested.