Yesterday I went for a run in the park. In my old days, before I started improving my pick up and dating skills, I would run early in the mornings, before sunrise so as to get it done at the start of the day. Now, I’m finding that running can be used for both physical exercise and as a way to socialize and meet women.

Within a minute of starting my run I notice a really attractive woman walking on the sidewalk. She’s got one of those sexy hip movements going that accentuate her rear end – and a fine one it was. She’s wearing a thin tank top so she’s looking very fine indeed. So what do I do as I’m running towards her? I get nervous and decide I’ll have to let this one pass. I think I said hi to her as I passed but I didn’t stop and start talking to her. I’m still trying to figure out a good way to start a conversation with a woman as I’m passing her from behind, since I know this can be startling to women since they don’t see me coming.

So as I’m kicking myself for not trying to talk to this hottie, I start to see in the distance another really attractive woman walking by herself! OK, this has got to be a sign from above that I need to put myself out there. This woman (mid twenties), who’s very good looking, isn’t dressed or walking as provocatively as the first one. That’s more my style, really – someone who’s very attractive but doesn’t flaunt it by shaking their money maker and wearing very skimpy clothing. I guess I prefer a more subtle woman.

And she’s walking towards me as I’m running towards her! OK, OK, don’t panic, don’t panic… think what can I say… as I get closer and closer I don’t even know if I’ll manage to say anything… but something inside me just forces me to stop as we get within talking distance of each other. She stops, too, and I open with “Hi, didn’t mean to bother you but where’s the closest Starbucks?” Now I know where it is – it’s only 200 feet away from where we are and I’ve been to it dozens of times. But I didn’t know what else to say. She replies very matter-of-factly “Oh, it’s just over there” and points to where it is. I say thanks and then say, “OK, that wasn’t really the reason I stopped you. You looked really interesting and I wanted to say hi to you.” She says “hi” but gets a little of a weird look on her face. I say “And I thought we could talk”. Now she starts moving away from me in the direction she was originally going – obviously I scared her off. She just smiles awkwardly in my direction as she continues to walk away and I just say a lame “you don’t want to talk?” and she replies with a shake of her head and walks off.

OK, so from a pure results point of view, that totally sucked. But I’m not looking at it from that perspective. I was just happy that I tried my first pick up attempt while I’m running. I tried to do this before but couldn’t get over my nervousness to do it.

I felt great after that pick up attempt – so much so, that I tried another one on the same run…

Things I learned

  • Smile! I think that would put women more at ease when I start talking to them. If I’m nervous, they get nervous too. If I smile genuinely and warmly, there’s a better chance they’ll smile, too, which will put them in a more receptive mood to communicate.
  • Be direct, but not offensive. Women are smart and she probably felt I was disingenuous by asking her where the Starbucks was and then telling her I didn’t really want to know that. Maybe next time I can say something like “you look really attractive/sexy and I’d be kicking myself if I didn’t stop and talk to you”. I mean, that is the truth and I wonder how women will react to a very frank and direct approach like that.