Last night one of those ideal spring evenings – the weather was warm, but not too hot, the sun was shining and everyone was outside enjoying themselves. I went running through the park and there were a lot of people – families out for an evening walk, the elderly walking in their groups and… (drum roll please) hot women out enjoying themselves.

I wasn’t in a particularly pick up mood, to be honest. I’m still not totally comfortable trying to pick up women while running – it still seems a little foreign to me. I was determined, though, to practice being social and friendly – I made it a point to say hello to almost everyone I would pass. This time, though, I would smile warmly and say hi in a more open and friendly way. So it wasn’t like a “drive by” hi that I say at the last second as I’m passing them by. Instead, I would smile and say hello to them when I was a good 20 feet away. That way there would be time to see them say hi back and smile. I’m even saying hello now to people that I pass by from behind, which I didn’t use to do before. As I pass them by, I look back, smile and say hello. Usually, they smile and say hello. It’s these little things that really help me be more social when I want to talk to hot women.

About half way into my run, I see a couple of attractive (mid twenties) women running towards me! I don’t see this very often so I wonder if this is a sign from above. But I wasn’t feeling confident enough to stop and start talking to them, so I only manage to say hello and smile at them as we pass each other. I’m kicking myself inside for not taking any further action. The fear of rejection or disapproval from woman is a powerful force for many guys (me included) that I’m really trying to tame and keep in its place.

I continue running towards my halfway point and keep saying hello to people I pass. I get to my halfway point, turn around and start running back. I start thinking of ways I could incorporate practicing picking up women while running without having to actually do it each time. Kind of like my daily morning pick up practice where I say hi to people in my neighborhood. I’m almost out of the park by now and am ready to start running for home, when I see the same two women running towards me again! So it looks like they turned around the same time as I did.

My thought pattern went something like this:

OK, this is it, this is it! This is a perfect opportunity. What have I got to lose – if they say no, I’ll just continue running for home and chalk it up to another learning experience. One of them is really hot and this could be fun!

So as we get closer to each other I say hello again. As soon as we pass each other, I turn around and in a matter-of-fact tone say something like “Hey, you guys mind if I run with you?” They look at each other not knowing what to say, so while they’re caught in this pause I just run up to them and say “I know it might seem weird and all, but why don’t we try it and if after a minute it’s not working I’ll be on my way.” They shrug in a “why not” kind of way and we start running together.

I’m pretty upbeat and friendly, asking them questions about their running, if they’ve been in this park before and what they do. Turns out they’re from a different part of the city but not that far away. After a few minutes of talking, I introduce myself and they tell me their names – Heather and Nina. They both seem nice but I’m definitely more interested in Heather than Nina. She’s got this sexiness to her but she also seems friendly and open. As we’re talking, Heather even asks me a few questions about my running and some of my running gear. I take that as a good sign since she wouldn’t be asking me things about myself if there was no interest. The whole vibe is pretty friendly and casual. Turns out Heather is a fitness trainer (yes!) and is teaching Nina how to run. They do a combination of running and walking so we end up walking for most of the time, which is OK with me since I’ve already done most of my run. Heather tells me a little of what she does, too, and how she works with kids. I make a few light-hearted jokes about one of her stories and we all laugh, which breaks up the tension. We spend about 10-15 minutes just walking and talking – there’s a connection there but it’s still hard to say if the connection will grow deeper.

We also have some gaps in our conversation, too, but I wasn’t as concerned about it as I would be in the past. In the past, I’d be desperately trying to keep the conversation going all the time. Nowadays, I’m OK with having a few gaps in – it’s normal and nothing to get hung up about.

I eventually tell them that I should be getting back and that it was very nice to meet up with them. They tell me the same and I’m debating whether to ask Heather out. What the hell, I go for it…

As we’re saying our good-bye’s I say, “Listen, I don’t usually do this kind of thing, but would you guys like to go out sometime?” I didn’t really ask Heather out, I kind of asked both of them out at the same time. There’s a pause, they look at each other again, and Heather says “Why don’t we run into you here again and we’ll take it from there?” I say, “Yeah, right, like I’m going to see you guys here again – you’re not from this area.” I just look at them, without saying a word, with a “why not?!” expression on my face. After a few more seconds, Heather says, “I have a boyfriend.” Then Nina says “And I’m engaged.” So I just say, “OK, no problem.” It got a little awkward for a bit there but I try to ease the tension by wishing them luck in their training.

I got the sense that I was close to Heather saying yes. A thought that came to me afterwards was that I should have made some kind of an arrangement to meet up again at the park. That way, she’d feel safe and wouldn’t have to give out her number or make any commitment, while at the same time keeping an opportunity open. I’m not sure I bought the “I have a boyfriend” excuse because why didn’t she mention it after the first time I asked her out? I think she just wasn’t ready to give me her number – but I think there was an interest there.

I ran back home, feeling great about what happened. I’ve never started a conversation with two women while running and actually had it continue for that length of time (10-15 minutes). I kept saying hello to people for the rest of the run home and I felt good about having put myself out there. I’ve said it before but I need to keep reminding myself – it’s more important that I tried picking up than whether I picked her up or not.

Things I Learned

At the heart of approach anxiety and fear of rejection is the fear that someone won’t approve of us or think we’re strange or weird or stupid. The same fear that kept me from not saying hi to people that looked like they were busy talking to other people, kept me from not approaching Heather and Nina the first time we ran past each other. I just thought it would be too weird – more precisely, I thought they would think that I was weird. By continuing to say hello to virtually everyone I passed, I conditioned myself to think it’s normal to start talking to people that I meet while I’m running. Picking up women starts in the mind, long before the first word is uttered.

I spent time building a connection. It would have been nice to spend half an hour with them – and maybe I should have! But I felt that our conversation started to lag so I thought that would be a good time to excuse myself. In the future, it would be nice to see how long I can stretch the interaction. The longer we talk, the better my chances of her saying yes when I ask her out. I found this to be the case when I picked up Anna at the bookstore.

I should have focused on asking out Heather, the woman I was interested in, instead of both of them. I wanted to be nice and extend the offer to both but I was really only interested in the more attractive one. Sure, it might seem less threatening if I ask them both out together, but I could have directed my gaze on the one I was interested in while asking her out.

I liked that I didn’t walk away right after their initial resistance to me asking them out. I tried again by saying that we’re not likely to run into each other again and then just looked at them. Now, maybe that wasn’t the best way to go about it, but at least I didn’t give up as easily as before. This is something that I’ll develop as I practice more pick ups. I find that women tend to resist new interactions – maybe it’s a safety mechanism and/or social conditioning, but I think I can eventually get past that so they can see that I would be safe and fun to hang out with.

I was fairly easy going throughout the interaction. I wasn’t that nervous, even though I started talking to a couple of women and one of them was quite attractive. This is great progress, since in the past I tended to get nervous when talking to hot women. There’s still a lot more work to be done here, but I can feel myself improving.

I made sure to include both women in the conversation and not just the one I was interested in. I like this approach since it shows I’m a generally friendly person. If I was in a group of new people and there were guys there, I’d talk to them, too. I think too many guys only focus on the one woman they’re interested in and that can come off as too intense and unfriendly.