Looking for advice on approaching an older woman

[euphoria9050]

Hey all,

I was wondering if anyone could give me some pointers in approaching an older woman. In my case, i'm wicked shy in approaching women my own age so the prospect of approaching someone older than me really makes me sweat. I've always been into older women but when i go to approach one i get very nervous.

Its not for a lack of confidence in myself, is more that i'm afraid of not having anything in common with them and getting the "cold shoulder" Could someone give me some advice on avoiding this?

Hope everyone is well,

Dave

[southernfinest]

Confidence...thats all it is, being scared nervous and shy might catch a few cougars but if you're straight forward and look confident you should have no problems talking to someone.
Reassure yourself and dont be afraid seriously. I first approached a cougar when I was 17 *told her I was 18, dont know if thats bad or not but it was fun * but because I gave it a shot and had the balls to ask her for her number everything worked out fine

[euphoria9050]

Thanks for the feedback! I guess you can't learn to swim unless you jump in. Unfortunately i have a tendency to sink lol

[southernfinest]

Thx Tarni thats basically what I was trying to say

[blueize]

Hi,
I think it's hard for people to meet someone they're extremely interested in, because it feels like a make-or-break, win-or-lose, live-or-die situation. Play it down into a friendship scenario. Treat her like she seems nice so you should both chat. That way if she's a cold shouldered gal, your investment was pretty low.

If you chat for a few minutes, look for common ground like: seen any good movies? What are you drinking? -Is it good? If she is in shape, ask if she follows teams sports; she might have a hobby or sport you can chat about. This is easy in any bar or restaurant with a TV.

A casual compliment is always nice. I've heard everything from, "I like your skirt" to "Those are nice shoes." -From guys who probably didn't even look at the skirt or shoes.

Just keep it friendly. The sexiest thing a man or woman can wear is a smile! Have fun!

[euphoria9050]

Wow you all give really good advice! I think i have a few good suggestions to start from. As Blueize said, i think when i go to approach someone that interests me a lot, i get intimidated and start playing through all the rejection scenerios in my head. Before i know it, i am so flustered, i don't even give the person a chance to say no. I like the "thinking of friendship first" approach, maybe that will take some of the pressure off.

Thanks to everyone that has offered advice. It is much appreciated!

[ttorssen]

This worked for me. I have been looking at this very nice woman in her 60'ties (I am 26) for long time. She owns a shop for classic women's close and she dress so nice as well and at the same time expose her mature body so well. I pretended to be gift shopping but she did not respond to my smile and comments. I find out that she also plays tennis at my club and manage to see her. I managed to say that new we see each other both in her shop and here, why not have coffees, she smiled and responded why not. She looked great in her tight leather pants (that exposed her little extra padding and maturity) and high heels. Every time we were dancing I try to keep holding hands with her, but at last she said she enjoyed the evening and we could repeat, but I was too young for her style - I still work on her, but it is diff. any good advisees on this one???

[blueize]

It sounds to me like she likes you, but is uncomfortable with either the age difference or something else that makes her socially uncomfortable. I would evaluate 2 things: first yourself, then the competition (for 2 different reasons).

She said you aren't here style, and you specifically mentioned her style. It is possible that she is looking for a partner who represents her choice of social strata. Since she expresses this with her clothing, she may be looking for a guy in something that matches the degree of formality of what she wears. A woman in leather pants probably is not looking for a guy in either a suit, or jeans. I can't see her clothes, but you can. Ask a female friend or a gay man to go to her shop and tell you what style she is looking for.

As far as evaluating the competition, she may be settled on dating guys of a certain age, or guys who wear tennis sweaters, own yachts and drink scotch. Whatever it is, it's kind of like someone who only drives an SUV, or only goes on cruises on vacation, or only... whatever. My guess is if you are an occasional friendly date off and on, you may be able to win her over with "gentlemanly maturity." Specifically, watch some 1950's movies and watch how often, men held doors open, and did those kinds of things. Whatever she is looking for, if you are observant, over time, you may be able to ace out the guys in her usual crowd.

Good Luck!

[haberdasher]

I would recommend be up-front with her about her "hang up" of not liking a younger guy. You want to paint it as a type of discimination. That way she will feel like it is unjustified for her to feel that way. Tell her that she is "buying into" society's myths and false rules about who she can date; in a way she is letting society dictate her behavior to her. Once she sees that she is doing this, she will likely be angry at herself for letting society dictate her behavior and not being her own person. And take it from me, the more adamant you are about this position, the better.

[robynneazura]

I was told that older women move at the speed of light. If they give you the sign and you don't respond immediately, then she won't give you a second chance. This older woman has given me all the signs. At one point it was really strong, but I had not the heart to look her in the eye. In the end, I gathered myself together and tried to engage in a conversation with her. It was small talk that lasted less than a minute. I might have made her feel uncomfortable. If I had better things to say, I would have said it, but my mind was travelling in the fast lane when I approached her. I felt like a student to a professor. The reader may have an idea how I feel, if so I would very much appreciate any advice as to how I should approach her in the next time, if there is a next time...
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