Whoa, really cool I see this post now. I have a story.

3 days ago, I had that exact experience, for only the second time in my life. I was biking around Bde Maka Ska (a popular lake in Minneapolis that people flock to when the day is gorgeous), riding fast, no-handed, dressed in goofy green cargo shorts, white legs, a saggy black v-neck tee, old old out-of-style black Nike shoes with no laces, and one of those black, military-style not-swoopy helmets that has a little bill on the front.

I was breathing really hard and needed to rest. I stopped on the grass, got off the bike, took off my helmet and looked at the lake. A woman's voice behind me says, "excuse me". I turned around, and there was a very attractive woman, maybe 48-52 years old, standing by her bike about 5 feet away, looking at me. I'm immediately smitten and I don't know what to say.

But I said "hi" and she then says, "I just wanted to tell you that I like your style, riding with no hands like you're really enjoying yourself and showing that to the world. People don't do that enough."

I blathered a bit about something, like why I was doing it, how it was goofy or something. I wish I could remember. My entire thinking was "enjoy this moment, it will end, we'll both ride on and never see each other again." I remember actually thinking this. She said "I just wanted to tell you that", I said "thank you" and smiled, then she said "Enjoy the rest of your ride. Bye!" and she rode off.

I watched her for a minute - her movement was athletic and easy - she rode no-handed, too. My breathing slowed to normal and I started riding again. I decided I wanted more conversation, so I eventually caught up and said "hi". I then said something completely non-sequitur - "do you know any of the Woodling (my last name) kids?", as if her looking younger and maybe looking like an expressive artist would mean she might have met one of my kids at some point. Truthfully, she kind of looked like my oldest son's girlfriend, who's a dancer, which kicked off a whole rapid series of thoughts about artists and community and shit unrelated to the moment.

She said no. Then, "are you married?" I said "separated, a long time." She said, "well maybe you should get divorced so you can date." I said, "I think that's a good idea." Right then, my path toward home came up and I said "I'm going that way." She said, "ok. Bye. Nice to meet you." And we road on, and that was it.

I had thought early on that this conversation is going to end and we'll ride off and that will be it. I made exactly that happen. I could have said, "would you sit down with me for a minute and talk?", or "may I have your number so I can call you when I get divorced?" I did none of that, because I'm so wrapped up in how I think people see me or how they think of me. I couldn't seize this moment, when a woman who looks exactly like the kind of woman I want to know and be with comes right up to me, maybe throwing caution to the wind (or maybe it's just how she is), and says to me something lovely and complimentary and kind and fun, and I can think of almost nothing but how I must appear to her.

My advice is, stop for a minute, look at who's in front of you, figure out how to value that person and that moment, and return the kindness that's being offered. Nothing more than that. But make sure you stop to value it. I don't know if I'll ever see her again, but I'm going to try. I know her first name and I know she was riding her bike around Bde Maka Ska at sunset on a Sunday. I'll work with that and try to thank her for reaching out. That's it.

Matt

I could never go up to a man but I’m a pretty good flirt from a distance.

I start conversations all the time because I enjoy people; unfortunately for my single life, most of the people I run into in daily life are married or partnered. Still nice to chat with, but no dating potential.

I wouldn’t approach a man. They seem to take it as an invitation for casual sex. Men can come to me, and they can wait...

I have no problem in engaging with people of both sexes, I am gregarious by nature and have no difficulty striking up a conversation. Whilst saying that, I don’t think I would ask a man out on a date. If I had initiated the conversation and it seemed we were on the same wavelength I think I would still want him to ask me out. Maybe that is because it is in my psyche that I think that is how dating should work because being older that was always the accepted norm,

Its not a sex thing but a sensual endeavor. Or just fun flirting. Sometimes it can become a sensual and sexual experience...if my memory serves me well

My younger girl friends have no problem doing that. Me, I am too shy and can rarely even make eye contact with a guy who I find attractive. Unfortunately, I seem to be attracted to guys who are also shy, haha!

I think it stems from my old fashioned upbringing that girls don't call boys, don't make the first move, etc. I like to think I'm getting better, but nope, I'm not. Still shy. Have no problem starting a conversation with someone on a purely platonic level, with no attraction really. But at my age, that's probably the best start anyway.

Its not a sex thing but a sensual endeavor. Or just fun flirting. Sometimes it can become a sensual and sexual experience...if my memory serves me well

I feel like I'm always the one to initiate conversation ?

What do you mean by "in today's world"?

As a cheerful, born flirt, it's not even a sex thing. I flirt with everyone- men, women, children, animals, customer service people on the phone, automated phone lines ("Press 3 for more options? Oh, darling, I don't think you have a button for the option I'd like" ).

I approach men, usually at the gym.

"How long have you been working out?" I ask. Conversation begins.

Probably.