I exercise regularly and my sport is running. Usually when I run I’m pretty concentrated on my run and not that social. Today, though, I wanted to break out of my pattern and talk with more people along the way that I would pass. And if there happened to be attractive women that passed my way, then all the better reason to stop and start talking with them.

First opportunity to practice came as I was leaving my building. I see this cute Asian woman standing outside my building smoking (OK, that part was not really cute). As I’m opening the door to the lobby, she comes in from outside and starts looking at the directory of names so she can get in the building. I just start joking around with her and say something like “you don’t look like a dangerous person so I guess I can let you in”. She looks at me, not understanding what’s going on for a second and then gets into the game with me – she starts saying how she can be trusted and how she’s not that dangerous. We keep joking around for a few minutes as I hold the door open for her and she walks in. As I turn to get ready to go outside, an older woman that’s been out walking her dog is about to come in, too, so I say hello to her and we have a brief chat, as well.

OK, so now I’m finally out on my run and I’m feeling happy, easy going, relaxed and friendly. I say hi to almost everyone I pass and it doesn’t matter whether they’re men, woman, young, old, attractive, unattractive. I found that put me in a totally upbeat mood so I’m not as serious as I usually am when I run. The ironic thing is that I didn’t feel as tired as I normally do after a run and I didn’t run any slower. OK, so I stopped a few times to talk with people but I felt more energetic as I was running.

I pass by this 65ish looking woman and say hello to her and smile. As I pass her she calls out “Can I ask you a question?” I figured, hey, someone wants to initiate talking with me instead of the other way around, so I said sure. But then she asks me some weird/deep questions right away like “Do you believe you have a soul?” Now, I’m all for deep philosophical discussions but come on! I just said hi to her, that’s all. I try to understand where she’s going with her questions and eventually she tells me she practices yoga and has this yoga center and gives me her pamphlet. I thank her for it and think that would be the end of the interaction. But she keeps talking! She tells me that she wouldn’t have called out to me at all had I not said hi to her first. I’m trying to be polite but after a while I say I have to run – literally. She continues talking until I finally have to get less polite and I say I have to run and start running away as we say good-bye.

I get to a park that has a nice path and I see a group of three 50+ women walking their dogs. I say hello and start talking to one of them about her dog. As we finish up and I get ready to get back on my run I turn around and – BAM – I see this very attractive woman running towards me. A perfect opportunity is right in front of me… I panic… she’s really close to me by the time I notice her so I don’t have a chance to think of anything to say and I give in to my fear and just watch as she runs right by me – I don’t even say a word. That was rather disappointing but I try not to dwell on it and I continue my run in the park and continue saying hi to people.

About halfway through I meet this older looking guy and we start talking. Turns out he’s 92(!!!) but I swear he could pass for 65. I’m curious about his longevity and he tells me he walks an hour seven days a week and swims and practices yoga regularly. Amazing – I learned something really valuable from him and I don’t think I’d have talked to him if I wasn’t more open to possibilities today.

Then I ran by a grandmother walking a stroller with her grandchild. I stopped and talked to her and I played a little with the baby boy – again, something I wouldn’t have done previously when I’d be totally focused on my running. As I finish up playing with the little boy and say good-bye, I turn around and again – BAM – another really cute woman is running by herself towards me! But again, she’s already very close to me by the time I notice her and I just managed to say a really feeble hi as she runs by. Man, that’s twice today I let a great opportunity run right by me – literally. What’s with that? In my imagination, I was planning on seeing the woman up ahead, as I’m running towards her. I’d say hi as I’m getting close to her, stop running and start talking to her. But the way those two women appeared out of nowhere totally messed me up.

I collected my disappointment, again, got back in a social mode, and continued running for home. I ended up stopping to chat with another baby and grandparents group along the way but this time no hot woman appeared after I stopped talking with them šŸ˜‰

At the end of my run, I had this crazy idea – why don’t I go into a Starbucks coffee shop, with my running gear and all, spot out an interesting looking woman that’s sitting by herself and go and start talking with her and if the vibe is good, even sit down and continue talking with her – like a spontaneous date or something – all in my running gear. I got as far as running past the Starbucks and checking out the people inside but didn’t have the guts to come inside. Guess I felt that would look too weird – some guy who’s been running just comes in and starts talking to some woman without even buying anything (I don’t carry any money on me when I run). But then again, why do I care so much?

Even though I didn’t come inside, I ran next to the coffee shop so I could see who was inside. There was a woman who looked like she was studying but my feeling is that if you’re studying in a coffee shop by yourself, part of you wants to be distracted by talking with your friends or with some guy who notices you from the outside and comes in to start talking to you and you end up having this fun time. So it’s a bit out of the ordinary but I bet that would have made that woman’s day or even week. Ahhh…. I don’t feel I’m ready to do that yet, but I think eventually I will be.

I also locked eyes with another woman who was sitting with some guy at the edge of the store. We must have been less than feet apart as I passed her, separated by a plate of glass. We definitely had that “eye lock” where we glanced at each other and connected without saying a word. I just smiled as I ran by her and she smiled at me – I mean, what was I going to do – come in and sit with her and the guy she was with? That’s definitely in the advanced section of whatever course I’m on.

So I’m realizing more and more that starting conversations with women in public places involves being a more social person with all people, not just with women I’m attracted to. I must have talked to or said hi to at least 20 people while on my run. I got into about 5 conversations with people but they were mostly older people. I totally didn’t do anything about the two women that ran by me and I didn’t go and talk to the woman in the coffee shop so I guess it’s something I’m not ready for yet.

Despite the setbacks, I’m feeling great overall. I still have a long way to go before I can just approach any woman I want but I feel like it’s definitely doable. I mean, I can actually envision myself doing it, whereas before, it just seemed like a very remote possibility. The vast majority of people I came across were very friendly and open. Sure, a couple of times I said hi I got totally ignored but hey, that’s to be expected so I’m not taking it personally.

So until next time, have fun and play safe.