Need help flirting with strangers

As old and ugly as I am women flirt with me all the time, it happened again a few minutes ago outside. Women, total strangers, approach me at the library and other places. They do it in front of my wife. My wife did the same when we met 40 years ago. I was at the laundromat, she came in, and sat on the washer in front of me, and the rest is history. I've learned to wait for women to express an interest in me, I don't chase them or pester them with PMs.

So what do you do.....hang a $100 bill out of your fly?
 
Flirting

Im the same so shy, I blush when a girl talks to me would somebody like to help?
 
Thanks everybody. I'll go practice tomorrow and report my successes back :).
 
Thanks for the comments - I know eye contact is the key and am working on that. I just don't know why it's so hard for me to overcome my habit of looking down as I pass a man on the street. Maybe I can picture something I'm mentally asking each person, or something I'm curious about (eye color, etc) that would allow me to break that conditioning of looking away or down.

Grrl, just went and read your stories and left a comment. Hope you'll write some more, they're good! :)


Aww - thanks! :eek:

Glancing, friendly/happy eye contact (look, smile, maybe blush, look away, then peek again) doesn't have to be a big deal. :) Even if you cannot pursue things beyond eye contact, most people will appreciate a smile.
Not everyone will notice you trying to catch their eye - they might be on a mission, or trying to not interact with strangers (particularly when you go to the city). You can't win them all, but if you try and make eye contact, then you're not depending on them to invite you in - you are extending your own friendly invitation to the world. :)
 
I need some help with what may seem like a silly question.

I am a very flirtatious person, but I am unable to flirt with someone unless they indicate interest first. I'm trying to retrain myself about flirting with men on the street. I'm not normally a shy person - I talk, flirt, joke - very comfortable with lots of attention. But for some reason on the street, I drop my eyes rather than make eye contact. I can't even flirt w guys in the next car over - it's like intense stranger shyness, but the moment they express interest, the wall immediately drops away and I'm perfectly comfortable flirting outrageously. So why is that???

I am trying to force myself to make eye contact and smile, flirtatiously if I like what I see. But yes, I love to walk by a guy and see them watch me, or show (subtly and not crassly) that they think I'm hot. If they do. I love the idea that after I walk by, they turn to watch my ass. :)

So, ladies, how do you flirt with a man on the street?

Men, how do you like for a woman to catch your eye on the street? And if she's hot, how do you let her know you think so?

And all, does anyone else have this situation of extreme shyness in one area that doesn't seem to fit your overall personality and sexuality at all??

I totally get your hesitation, it can be hard to tell if a guy is 'hooked', especially when meeting people out in the busy, hectic world. But go for the three questions rule:

After the initial greeting/exchange, ask him three questions. If he's reading a golf magazine, ask him if he plays. If he says yes, ask him if he has ever had a caddy, etc, if he says no, ask him why he's reading a golf magazine, etc. If he drives a nice car, ask him what kind it is (even if you know...), ask him why he chose that color, ask him if its a manual, etc. If he isn't into following a 3 question sequence, he's probably not into chatting.

If you really just wanna flirt with a guy and get a date/number/email address, you an totally just brute-force it:

Laugh at whatever stupid shit he says. You're just trying to get his attention and get a callback--you can decide if you ACTUALLY think he's funny later.

Cleavage. Yes, I am not joking--perhaps minorly degrading, but it will get attention. Even girls with small boobs can just wear low cut shirts--guys are mainly just into the big expanse of exposed skin. But if you have big boobs, that definitely helps!!

Now, this doesn't even mean you have to walk around looking like a complete slut all the time, you just have to know how to ADJUST your clothes when you are going into action. Attached two pics--first one I'm wearing a t-shirt with a low neckline, I wouldn't call it conservative but nothing insanely trash.
But if I was going to go up to a guy and talk to him, I'd adjust the shirt to look like the other pic.

If you have a tight t-shirt like this, you can just grab the fabric behind the shoulders and pull it forward--note the top seam is not visible at all in the first pic, hidden behind my back; but in the second pic the seam is pulled so far forward it is resting on my collarbone. The neckline is markedly different, as you can see.

tl:dr
Act interested, laugh at his jokes, cleavage. You can do this.
 
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I totally get your hesitation, it can be hard to tell if a guy is 'hooked', especially when meeting people out in the busy, hectic world.

Oh I'm golden whenever I can talk to someone - no trouble with that at all. It's just passing someone on the street and giving the flirtatious smile and receiving one in return that I struggle with. You have any tried and true methods for that? :)
 
Wearing that shirt would get my attention either way. WOW!!! I think the hard nips in the first pic is more sexy than showing the cleavage. But that's just the my onion.:devil:
 
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just fling poo on them. worx for Munky every time. Munky poo afrodeeseeack
 
I totally get your hesitation, it can be hard to tell if a guy is 'hooked', especially when meeting people out in the busy, hectic world.

Oh I'm golden whenever I can talk to someone - no trouble with that at all. It's just passing someone on the street and giving the flirtatious smile and receiving one in return that I struggle with. You have any tried and true methods for that? :)

again, why not brute force it. You can just say "Hey," and when they turn to talk, you could just go ahead and be like "I totally think you're cute. You want to exchange numbers?"
 
You can remain demure and flirt.
Star at him when he's not looking, then when he notices (and only after you're sure he noticed), look away nervously. Repeat until he walks over (he will walk over).
 
[/QUOTE]

This one would be enough for me to call you
 
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Nervous. Husband is going to help me get over my stranger anxiety by having me dress somewhat provocatively tomorrow and practice catching the eye of strangers while we're out of town. Should be fun and scary all at once. Wish me luck.
 
Nervous. Husband is going to help me get over my stranger anxiety by having me dress somewhat provocatively tomorrow and practice catching the eye of strangers while we're out of town. Should be fun and scary all at once. Wish me luck.
Good luck!!! Fun for you both.
 
Good luck!!! Fun for you both.

Don't you want to come shopping with us, Loaded? I could practice flirting with you and it wouldn't be so scary, you know, to kind of warm up :).

My instructions are to wear clothes that show off my curves and release my inner MILF while still staying classy (my words, not his). Bag is all packed for changing into the sexy clothes on the way - we'll be coming back from out of town and stopping en route.
 
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I always say hello

I need some help with what may seem like a silly question.

I am a very flirtatious person, but I am unable to flirt with someone unless they indicate interest first. I'm trying to retrain myself about flirting with men on the street. I'm not normally a shy person - I talk, flirt, joke - very comfortable with lots of attention. But for some reason on the street, I drop my eyes rather than make eye contact. I can't even flirt w guys in the next car over - it's like intense stranger shyness, but the moment they express interest, the wall immediately drops away and I'm perfectly comfortable flirting outrageously. So why is that???

I am trying to force myself to make eye contact and smile, flirtatiously if I like what I see. But yes, I love to walk by a guy and see them watch me, or show (subtly and not crassly) that they think I'm hot. If they do. I love the idea that after I walk by, they turn to watch my ass. :)

So, ladies, how do you flirt with a man on the street?

Men, how do you like for a woman to catch your eye on the street? And if she's hot, how do you let her know you think so?

And all, does anyone else have this situation of extreme shyness in one area that doesn't seem to fit your overall personality and sexuality at all??


I'll nod and say hello.

Why be coy?
 
Red Lips

I totally get your hesitation, it can be hard to tell if a guy is 'hooked', especially when meeting people out in the busy, hectic world. But go for the three questions rule:

After the initial greeting/exchange, ask him three questions. If he's reading a golf magazine, ask him if he plays. If he says yes, ask him if he has ever had a caddy, etc, if he says no, ask him why he's reading a golf magazine, etc. If he drives a nice car, ask him what kind it is (even if you know...), ask him why he chose that color, ask him if its a manual, etc. If he isn't into following a 3 question sequence, he's probably not into chatting.

If you really just wanna flirt with a guy and get a date/number/email address, you an totally just brute-force it:

Laugh at whatever stupid shit he says. You're just trying to get his attention and get a callback--you can decide if you ACTUALLY think he's funny later.

Cleavage. Yes, I am not joking--perhaps minorly degrading, but it will get attention. Even girls with small boobs can just wear low cut shirts--guys are mainly just into the big expanse of exposed skin. But if you have big boobs, that definitely helps!!

Now, this doesn't even mean you have to walk around looking like a complete slut all the time, you just have to know how to ADJUST your clothes when you are going into action. Attached two pics--first one I'm wearing a t-shirt with a low neckline, I wouldn't call it conservative but nothing insanely trashy:



But if I was going to go up to a guy and talk to him, I'd adjust the shirt to look like this:


If you have a tight t-shirt like this, you can just grab the fabric behind the shoulders and pull it forward--note the top seam is not visible at all in the first pic, hidden behind my back; but in the second pic the seam is pulled so far forward it is resting on my collarbone. The neckline is markedly different, as you can see.

tl:dr
Act interested, laugh at his jokes, cleavage. You can do this.


I'm digging your lips. That would work for me
 
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Don't you want to come shopping with us, Loaded? I could practice flirting with you and it wouldn't be so scary, you know, to kind of warm up :).

My instructions are to wear clothes that show off my curves and release my inner MILF while still staying classy (my words, not his). Bag is all packed for changing into the sexy clothes on the way - we'll be coming back from out of town and stopping en route.

Kerali, if I may ask, what kinds of outfit will you be wearing? What about those clothes do you like? I find it a bit hard to hit that 'sexy and classy' register myself, sometimes, and I often err on the side of being too conservative. :eek:
 
flirt

Do you want it to lead to dirty flirting? If so don't be shy. A guy wants to hear what's on your (dirty) mind. 99% of the guys here want you to ask them something sexual. Guys are looking for sexting, an to exchange pictures. Guys want to hear how horny you are. They want you to ask them what they are wearing an doing right now, and what's on their mind.

So loosen up and don't let your inhabitants get I the way. Kik me, dirty chat
 
Don't you want to come shopping with us, Loaded? I could practice flirting with you and it wouldn't be so scary, you know, to kind of warm up :).

My instructions are to wear clothes that show off my curves and release my inner MILF while still staying classy (my words, not his). Bag is all packed for changing into the sexy clothes on the way - we'll be coming back from out of town and stopping en route.
I'd be a great team player!
 
Kerali, if I may ask, what kinds of outfit will you be wearing? What about those clothes do you like? I find it a bit hard to hit that 'sexy and classy' register myself, sometimes, and I often err on the side of being too conservative. :eek:

Grrl, I went with a cobalt blue skin-tight tank that was semi sheer if the light hit it just right, jacket over that was open down the front, trumpet denim skirt, high heeled boots, and of course under was deep plunge black push-up bra and matching lace boy shorts, garter belt and black thigh high stockings. Little more makeup than usual. Wanted it to be sexy enough to turn heads but not so sexy that I'd be mortified to run into someone I knew.

Unfortunately there weren't many folks to flirt with - no good looking men and only one gorgeous salesgirl and I did flirt with her. But we had a hot ride home and even hotter evening :). Hope that description helps.
 
Mmm, thanks Kerali! That outfit sounds gorgeous. :) Were the stockings sheer, or opaque?
 
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