Yesterday I managed to approach two women in one day so I’m publishing the first approach now and the second later today.

I went out running last night to wind down after the work day and to practice talking to women. I was feeling rather relaxed about that part and yet somehow determined. I think setting up the approaching women challenge and standing to lose $50 has really crystallized my focus on getting this goal accomplished.

I start running and, as is usual for me now, start saying hello to virtually all the people that I pass. I know this might sound like a trivial detail but I think it’s important: the quality of my hello’s and hi’s has been improving. If I’m feeling more shy/introverted I would say hi in a more neutral way. Also, I’d say it as I was just about to pass the person so I wouldn’t get a chance to see their reaction (lest it be a negative one). If I’m feeling shy I would often skip saying hello to people I’m passing from behind. But lately I’ve been noticing that my hello’s have been improving – I say it in a more friendly and open way. I usually smile when I say it. And I say it a good 10-20 feet in front of the person so I can see their reaction. It’s a little thing but it’s a good indicator that I’m getting more and more comfortable talking with strangers.

I have this determination in my head – I will talk to the first attractive woman I see. I will talk to the first attractive woman I see. I will talk to the first attractive woman I see. I can’t say I’ve ever felt this determined and sure of myself before. I don’t spot any hotties on the way to the park but I’m still feeling pretty upbeat. I’m hoping I run into Heather, who I almost picked up last week.

About five minutes into the park I spot a couple of women walking up ahead. The one on the left has a nice backside and the one on the right seems a bit older. I figure this is it. I’m running towards them and I’m thinking, “this is it, I can do it – I’m going to get my $50 back!” As I pass them I turn around and say hello to both of them and smile. The one with the nice backside seems fairly cute from the brief glance I got of her. And it looks like she’s walking with her mom. They seem a little startled and reply with a rather meek hello.

I continue running until I’m about 20 feet ahead of them and then I just stop and decide to go for it. I turn around and start walking towards them. When I get to talking distance I just say to both of them:

“Hi, I’m sorry to bother to you, but I saw you walking here (looking at the attractive one) and I just had to stop and say hi.”
“Um…. hi, ” the daughter says to me.

They have that deer-caught-in-head-lights look. I’m actually not that nervous – I just want to have fun, so I say something ridiculous to the mom like,

“I was running and when I saw her (glancing at her daughter) I just had to stop. You understand how it is.”

The mother just looks at me like I just dropped off the moon and says “Uh huh.”

But as weird as this might seem to you, I have a feeling they were flattered. I got a better look at the daughter and she turned out to be not as attractive as I initially thought – maybe a 6. But I figured it’s worth the practice. So I start walking with The Deer in the Headlights and the Deer’s mom as I try and continue the conversation.

“So, you guys live around here?”

“Umm… yeah, close by, ” the daughter replies in a guarded way. I can see this is going to be an uphill battle – I’ve caught them totally off guard.

After a few more exchanges like this I decide to cut my losses. The girl’s not that attractive anyway and she seems to be very closed off to interacting.
I just get really turned off with women that act this way – it sends me the signal that they’re no fun. I’m not one of those guys that makes it his mission to try and get a girl out of her shell – too time consuming and not worth it most of the time.

So after about a minute of walking with The Deer in the Headlights and her Mom I excuse myself by saying, “Well, it was nice to talk to you. Have a good day.”

I start my run again, and I’m feeling pretty happy and relaxed for approaching her. I even have this smile on my face and a minute later I pass by a group of 4 boys. They’re all about 10 and are walking on the path in the same direction as I’m running. I just say a friendly “Hi, guys” to them and after I run past them I hear all this talking and suddenly feet stomping behind me. I turn around and all four boys have started running behind me!

Two of the boys drop out after a few seconds while the remaining two continue running. I felt like Forrest Gump when he was running across the country and there were all these people that joined him on his run. I felt alive, free, liberated from my fears and I just didn’t care what people thought.

Feelings like this aren’t permanent, though. Close to my building, I ran by a gas station and thought I spotted a hottie filling up her car. I hesitated and didn’t follow through – I just kept running while I glanced at her in regret. She was totally focused on filling up her car and had no idea that I noticed her – so it would have been another Deer-Caught-In-Headlight approach. I guess I felt I met enough deer for one day.

It would have been nice to have approached two women in on one run again. I think if I was closer to my due date of my approaching women challenge I would have gone for it. I’m sure one day soon approaches like that won’t be a problem – the same way I just couldn’t stop and talk to a woman while running only a month ago.

Things I Learned

  • Having some extra motivation really helped me get over the last remnants of hesitation. If I hadn’t set out the approaching women challenge for myself, I could have easily rationalized to myself that the woman wasn’t that attractive or that she didn’t give me any indication she was friendly or interested. But I feel at this point I still need to push myself to get out there and approach more women. I think eventually, once I become very good at it, I won’t have to prove things like this anymore and can be more choosy who I approach.
  • I specifically wanted to try being direct but in a genuine and fun way. I know this isn’t the indirect approach that I thought worked better in the past but I think it’s too hard being indirect all the time. I mean, what was I going to do: say “hi, can you tell me where there’s a restaurant close to here?” We’re on a path in the park, I’m passing them by from behind, I see she has a nice backside and when I turn around to say hello notice she’s decently attractive. That’s it. I just find it makes me more nervous figuring out what indirect approach to take rather than just being direct and conveying the messages: you’re attractive, I’m interested in talking with you, and this could be fun. Granted, I didn’t get the desired reaction, but I think I can improve my delivery and approach.
  • I felt more motivated to complete my challenge, which made me feel more confident and relaxed. The last time I went running I didn’t stop to say hi to the hottie with the friend because I didn’t get any indicators of interest from her. Well tonight I didn’t get any either – the girl didn’t say hello back and she was walking with her mom. Yet I didn’t care as much as I did on my last run – maybe because the girl last night wasn’t as attractive as the woman from my last run. But I also think it’s because I’m learning to care less about what women think of me and to feel good expressing myself.