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How do you move from cheerfully flirting to being vulnerable?

As a cheerful, born flirt, my rationale is: "Why not leave people feeling a bit bucked up and perky?" I can flirt with anybody: men, women, teenagers, babies, grandparents, dogs, customer service representatives on the phone. It comes from an almost demented joy in being alive.

It’s fun to be in a momentary, twinkly conspiracy ("I like you, and you like me" ), laughing and talking together.

As men know, it is hard to move from lightly flirting to seizing the moment and being vulnerable.

It doesn’t help that my married hiking partner, Karen, critiques my comments to men afterwards. “Oh, Kathleen! I can’t believe you said that."

Occasionally, I run across a fit man my age who is hiking alone. Two years ago, while snowshoeing, a man took a shine to me. With an Italian accent, he was charming. I flirted as hard as I could. But did I set down my pack in the snow, dig out paper and pen, and give him my name and phone number? No. I didn't want to get my pack wet.

“You’ll run into him again,” Karen said consolingly. Fat chance. The chance of our converging on the same trail is miniscule.

A month ago, a handsome, older man – who climbed Mission Peak behind us- stopped his car at the trail head to chat with me. He focused on me, not the other women. Did I ask:

“Are you married?” - or even-

“Why are you hiking alone?”

Then I watched him drive away, kicking myself. I was wearing gloves; he couldn't see if I had a wedding ring.

I regret not being more forward with these two men.

What stops me is handsome, fit, middle aged men are usually married.

Perhaps I should have small cards printed with my name and phone number, like calling cards. I can carry a few in my pocket while hiking. Suave.

I'm bad about not carrying my phone while hiking. Too heavy. My hiking partners always carry phones. This bit me in the butt once, when Karen and I got separated on the trail.

Your thoughts? Do you have any suggestions?

p.s. Thank you @travelerx2 . Great idea!

Just clipped a pen to my hiking hat-band like old reporters, and pinned a folded piece of paper under the perky bow in the back.

Problem solved. Now I need to be more forward.

LiterateHiker 9 Sep 27

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Could always write your name and number on the inside flap of your pack and flash them with it.


Be naked. Bring beer. Very attractive to men. 😉

I’m cringing at this comment...

To the OP: please don’t think we’re all like this. You seem like you’ve got an interesting and active mind, you’re physically an active person - I think likely considerate and with a dry sense of humour (guessing a little here from what is gleanable from a few posts): these things are what make people attractive. I’m sure you’re a lovely person who doesn’t need either beer or nudity to be seen as such. Maybe just a little bravery to let people know you’re there? ?

I've been doing it all wrong. Thanks for the advice. I must try this. ?

VERY flirty.


Thank you for your kind, sweet comment. I appreciate you.

Drunken, naked women get more attention than those who are not. (you can look it up, usually in the police report.)


I can feel your pain.
As a guy, when you want to ask a lady our or tell her your interested, it can come off as pushy or overbearing.

To damn many Neanderthals messing with peoples heads and making them afraid of everything. Can never tell who's going to think what's over the top, and there are occasions where I don't say anything at all, then they think I'm aloof and uncaring

Dating, attraction, etc.. it's a real complicated thing

Angus Level 5 Sep 27, 2018

You absolutely have that right. All my life I've been accused of being a flirt - when in reality I'm just being friendly and outgoing. ????? Way too late for me to change my ways now! hahaha


HUMOR is the key. There is often something to find funny, laughing is sexy, it revs brain chemicals; nothing to it- simply pay attention to life.

And a good stretch to relax oneself can send a message...


Humor is key. I love making people laugh! Standing in line:

Me: "You know when your eyes are bigger than your stomach?"

Him: Laughing, "Yes, I sure do!"

Me: "Well, my eyes were too big when I bought this yellow mum plant yesterday. There's not enough room in my flowerpots."

Him: Grinning, "I love gardening, too."

And we were off!


Have cards printed that say 'International Woman of Mystery'.


Very funny! Great username.

@LiterateHiker thanks!


Hiking is starting to look like a great idea!!


"Forward" is a relative term.

I think it's amusing that you can describe yourself both as a "flirt" and as "not forward enough". Flirting in and of itself is more forward than many women can manage. I daresay most women are too withheld to even consider that strategy.

You clearly have the force of personality to be assertive; you perhaps just need to divert it from "flirting", to something more direct and concrete (and risky). But also, less complicated ... and trust me on this, most men will thank you endlessly for not being complicated or confusing. If you flirt but don't seek actual connection, that's mixed signals. We men are simple creatures. We like clarity.

If a man is not interested, that is generally not a slightest reflection on you, particularly since you're clearly an attractive, positive, curious and interesting person. It is just where the man is in life or where his existing commitments lie, or perhaps, a simple matter of taste (for which, as they say, there is no accounting).

If I were somehow transformed into a sauve, debonair creature, and a woman flirted with me but did not ask after my availability or contact info, I would be a bit baffled and perhaps disappointed, but it's the last you'd hear from me. So ... for what that's worth (two cents plus inflation, I imagine) consider the input and adjust accordingly. As a man, when I was "on the market", I found flirtatiousness to be a bit suspicious (though not an automatic deal killer) but direct, frank, open interest was, to me at least, completely disarming.


Have you ever been hurt from a relationship, of course, we all have! The memory of that pain tends to make us stop ourselves from being forward with others that we may find attractive and/or interesting. When you find yourself initially interested in someone push yourself to take a chance. Be careful to pay attention as to how the other person uses there words. Go over that initial conversation, write it down if necessary, and look for things that were said that may raise red flags in your head, about the other person. If we never take the chance, we may never know what could have blossomed! Good luck and happy hunting!! Sincerely...

Good advice, pay attention to their words.


Ask to borrow their phone, then add yourself to contacts. Smooth...


I give this li'l switch on my back a flip from 'Cheerfully Flirting' to 'Vulnerable'. You don't have one?


I once went on a hike with the Sierra Singles and found myself with a women that seemed nice. We got to talking and soon got on the sexy (not) subject of overpopulation. To my surprise she was interested. At the end i said good bye and we separated and I kicked myself. Sometime later we found ourselves on another hike together and this time I asked about her. She had just relocated to Seattle after getting her nurse practitioner license from Chapel Hill in family planning. She was looking for a place to live and I happened to have a lot of extra room. She ended up moving in with me. After 2 weeks we realized it was too far too fast and she moved into my basement apartment. After Over 20 years we are still friends. She is married now and lives in Bellingham. Point is sometimes you have to take the proverbial Bull by the horns and speak up. With your track record the first thing I would ask is how do you feel about Jesus?
BTW her name is Jill and we tell people we broke up because we got tired of the Jack & Jill comments (and there were lots).


A late friend who was an author once showed me a drawer full of rejection slips from publishers. He said: " I do not give up because my book was rejected, I keep on sending in my manuscript and sooner or later some publisher will want to print it. All I need is one."



The best place to meet people to fall in love with is doing what you love. If you find them out there doing the same thing, chances are you'll make a great couple. My wife and I were both teenagers when we met, working in the medical field. She as a nurse and I as a corpsman. We're still together! This is our 49th year.

jafbm Level 5 Oct 12, 2018




I like your story! This is usually the kind of question, as you hinted, that I hear from younger men especially. I will tell you what I tell them. Just put yourself out there that little bit more. Ask what are you doing up here alone? Or why didn't you bring your wife? That tells a sharp guy you are interested in more than conversation. But there are plenty of dull guys who are perfectly wonderful but will still think you are just requesting information. Like they're a trail guide of some kind. With them you must be persistent. Stand in front of him and question him closely if somewhat obliquely. You might find out all kinds of interesting things 🙂 good luck!


I have had that regret at not having been more bold many times, but I have also been shot down on more occasions than I care to count. I think the latter experience does tend to increase the likelihood of the former.


Flirting seems to be a sign of being vulnerable
Someone who is not vulnerable and confident will be straight forward and say what the feel without the feeling of possible vulnerability.


Flirting is great fun and it's safe, a little connection is a nice moment. If it moves on well that's where I'm complete shit and no use to you whatsoever 🙂

I don't know you but I love you. We got a direct connection.


It's possible you come on too strong for people who value peace and quiet, and the silent spaces in conversation. Those people wouldn't be a good match anyways, so nothing is lost there.


Some have no sense of humor. None.


One man didn't understand that in my post, "Being a Woman is Worse Than Being a Farmer," the author exaggerated for comedy. He's Portuguese. He wrote:

"I probably didn't pick up on it. Inglish isn't my first language and, no joke, this kind of stuff is presented as serious shit in Portugal sometimes. Apologies for my stupidity XD"

Being a woman is worse than being a farmer

@LiterateHiker I know. Now, I am paying more attention to the geographical location of our users. English is a tough language to master and we Americans are more often than not, horrible hypocrites to criticize those non-nationals who butcher our difficult language. I like to give the benefit of the doubt, but there again, some of the worst Trolls on the internet are those whose English is not their native language (I know, citation needed). Anyway, it is a tight-rope balancing act between being tolerant of language difficulties and taking out the trash. I even started a Group to try to identify spammers and trolls, but it is getting little traffic. I'm somewhat of an expert as I was Top Admin of one of the largest international forums during the last decade. I know, big deal. I did gain a lot of experience in identifying and expelling threats.


"What stops me is handsome, fit, middle-age men are usually married" or all they are interested in is a one-time hook up. You said "what stops me." I'm thinking you have a gut instinct not to proceed forward and give these guys your number, so trust your gut. However, if you want to begin to take advantage of these opportunities, simply say:

"Hey I enjoyed talking with you, and would like to talk some more. How do you feel about grabbing some coffee sometime?"

If he says, "Sure."

You can say "Do you know (fill in with some local coffee place)?" Then set a time and day.

Stick with a place that has people so you're not alone. Stick with a time and day that doesn't suggest a date that would end up with a hook up. I always used Sunday afternoon.

Wish I lived closer to you, I love to hike!! I'm headed to Montana and Canada next summer for a hiking trip.

Good luck!


Thank you for your good ideas and support. I'll try that. Wish we lived closer, too.


I'm horrible at it myself.
I am always friendly, but I'm fairly stupid at reading people.
Some one could be flirting with me, and I'm the last one to realize it.

You keep telling yourself this stuff, and it becomes a loop... PRETEND they are IF you don't know. How hard can it be? There is more to gain than to lose, no?


Memory weighs nothing. Tell him your number. It's his job to keep up with it. If he's genuinely interested he'll put his pack in the snow, while you move efficiently on up the trail. Or set up an email account with an easy to remember name, so he doesn't even have to write it down. Hi, I'm greenfriedtomatoes@blahblah, etc.

skado Level 8 Sep 27, 2018

You're right. My email is: hiker optimist @....

Easy to remember, I hope.

There ya go. That oughtta work!


my dad had cards that said something like hi my names .... i like chatting arguing drinking etc then his landline number he hated mobiles i lost count of the number of women i met at his house. His rational was women may feel uncomfortable giving their number and they can easily throw away the card later and it only cost him a few quid to get 100 printed


sex...lots of it

However at that early of a stage why do you care about the rejection...I mean the only vulnerability at that point. Chances are you may not see them again unless you carpe diem.
Risk reward equation only you can solve for you?


Spent my teens and early 20's realising just too late that the person I was flirting with was almost certainly more interested than I believed at the time. Go for it. Meet someone you like? Be bold and ask for a number! Or a drink. Or a whatever. How bad could it be?

EXACTLY. If one is rejected at least they tried! Why wonder, later???


What's more important to you, possible romance or a dry pack?


Good point.

@LiterateHiker I personally wouldn't be swept off my feet by coming in second to the dry pack.

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