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How to ask an older lady out without sounding creepy?


Hollywood-Tourist

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Hollywood-Tourist

Hi all,

 

I'm currently smitten with my local area Councillor who I know for a fact is single.

 

I desperately want to ask her out on a date/coffee meet but not entirely sure how to go about this without it coming across as 'creepy'?

 

I've emailed her about meeting up (to chat about local area concerns etc.) and we're scheduled to meet at the end of this month. She is 45yrs old and I'm 30.

 

I do feel that she may take me up on the offer of a drink based on how her punctuation was written on the emails we sent to arrange an appointment.

 

Can you advise please?

 

Thanks very much for your help.

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One step at a time. First of all, when you meet up on this one that is already arranged, do not act like you're on a date. But just maybe use that time to take care of business and then maybe ask her about her kids or see if she is open to talking about personal stuff or not. Then if you like her after you get to know her a little, you can tell her, You are a very interesting person and I'd like to get to know you better. Would you consider going on a date with me? But don't ask her at this meetup. Just talk and then ask later if you liked her and she seemed comfortable and all.

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Hollywood-Tourist
One step at a time. First of all, when you meet up on this one that is already arranged, do not act like you're on a date. But just maybe use that time to take care of business and then maybe ask her about her kids or see if she is open to talking about personal stuff or not. Then if you like her after you get to know her a little, you can tell her, You are a very interesting person and I'd like to get to know you better. Would you consider going on a date with me? But don't ask her at this meetup. Just talk and then ask later if you liked her and she seemed comfortable and all.

 

 

 

That's wonderful advice there and thank you for replying.

 

 

I think I will follow your advice about keeping it cool and casual and see where it goes from there.

 

 

I don't think she has kids by the way.

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Keep business and pleasure separate.

 

Ask her out, but make it clear, "no shop talk," and you'd like to take her for drinks/dinner. Are you dealing with a lot of community issues that can cause conflict, and would it be better to wait until after this end-of-month meeting to ask her out personally?

 

I really don't know how asking someone out is "creepy." It makes no sense to me that this is a creepy gesture. It's creepy if you get a "no" and keep asking and behaving as if she's playing hard to get.

 

I would be mindful of the community agenda and your involvement and wait until the major issues are resolved and calmed down, so there are no issues of fraternizing and what-not, but it's not creepy to ask a woman out.

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Just treat her like you would any other woman you're asking out. Im 48 and I've dated quite a few guys around your age in the last few years. None of them treated me like some different sort of creature and I think I would have been offended if they had.

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Hollywood-Tourist
Keep business and pleasure separate.

 

Ask her out, but make it clear, "no shop talk," and you'd like to take her for drinks/dinner. Are you dealing with a lot of community issues that can cause conflict, and would it be better to wait until after this end-of-month meeting to ask her out personally?

 

I really don't know how asking someone out is "creepy." It makes no sense to me that this is a creepy gesture. It's creepy if you get a "no" and keep asking and behaving as if she's playing hard to get.

 

I would be mindful of the community agenda and your involvement and wait until the major issues are resolved and calmed down, so there are no issues of fraternizing and what-not, but it's not creepy to ask a woman out.

 

 

 

I guess what I meant was that supposing I attended the meeting and it was kept strictly 'professional', then went home and after a few days sent her an email saying something along the lines of I enjoyed meeting with you the other day and learned a lot about the local communities etc. would you care to join me in town for a coffee maybe one day when you are free?

 

 

I was just worried that she would feel 'alarmed' at this and contact the cops.

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Hollywood-Tourist
Just treat her like you would any other woman you're asking out. Im 48 and I've dated quite a few guys around your age in the last few years. None of them treated me like some different sort of creature and I think I would have been offended if they had.

 

 

 

I would treat her with respect of course and would love to get to know her more. She could of course not be interested in me at all but I suppose if you don't try then you may never know what could have become of that.

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Why would she contact the cops if you sent a single email asking her out? It's illegal to stalk or harass, but not to ask someone on a date once.

 

Out of curiosity, what is it about her which has you so enamored?

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I do feel that she may take me up on the offer of a drink based on how her punctuation was written on the emails we sent to arrange an appointment.

 

did she sign her email with "xxxooo"??

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That's wonderful advice there and thank you for replying.

 

 

I think I will follow your advice about keeping it cool and casual and see where it goes from there.

 

 

I don't think she has kids by the way.

 

Good. Remember she could be gay, too. So ask her what she does in her spare time or has she any pets, etc. Just start seeing if she's willing to talk about personal stuff but take care of business first.

 

Nothing illegal about just sending one email. it's only if she says no and then you keep it up that things can go awry.

Edited by preraph
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hi d/f.

 

i think if youve emailed to talk about work stuff, then work stuff is really what you ought to be talking about, otherwise i dont think its going to look good for you, she will probably see through it pretty quickly and if she is not into you or taken then she might see you as wasting her time.

 

however, once you have met her you can always say at the end we ought to meet up one time after work for a drink and see what she says.

 

just be yourself and if you are nervous then the work stuff will keep you on track because you know the issues and she can contribute comfortably with those issues - so i dont think you will come across as creepy provided you stay professional.

 

i am sure she will be able to see through your meeting at some point if she is older i feel, but dont be put off by that thought, just let things go naturally and they will go the way they do.

 

maybe keep the meeting short too then suggest another meeting as you are saying goodbye...she will get the message believe me!!!! hahah...VERY GOOD LUCK. and remember, professional will win her respect. let us know (no not about the council matters!!!!! hahaha...but if you get to second base). good wishes. maxi ;)

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Younger guy finding me desirable enough to be asked out....I'd be all over that.

 

Be mature and confident in your approach.

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Don’t email her that’s lame just ask her out in person

 

Actually don’t even ask row just casually mentioned it like more like a hang out hey on Thursday when we go get something to drink or something along the lines of that ?

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