As I walk out of the Starbucks coffee shop I’m feeling pretty good – two approaches in one day and even though the last approach didn’t end up into a great exchange I still felt great for approaching a woman without hesitation in a coffee shop.

As I’m walking towards my building I spot an attractive woman walking towards me, by herself. I figure it’s time for another street approach – since I’ve got a lot to learn from my last street approach.

As she gets within talking distance I just lift my arms up and say in a carnival like tone, “I just have to stop you!”

She just looks at me like I’m some weirdo and keeps walking. I say, “Hey, where are you going? You’re walking out of my life for good.”

She just keeps walking and doesn’t stop.

OK, so you’d think that was a total rejection, but I’m actually smiling with myself at this point. I’m getting over the fear of approaching women on the street. Sure, she thought I was some weird lunatic, but that’s beside the point. I know I’ll get better at this.

I’m feeling almost giddy and say to myself, “I’m getting drunk from approaching.” and I almost start to walk a little funny. But I recover and notice this really nice old lady sitting in one of those walker/chairs right on the sidewalk.

I say hello to her and we end up having this great chat as I keep her company while I walk her to her building. She thanks me for talking to her (I don’t have a problem starting conversations with the elderly) and I think I just made her day.

Things I Learned

  • Doing something is better than doing nothing. Even if I get completely rejected, it’s better than getting nervous and not approaching at all.
  • Being a little zany/wacky scared her off. I’m wondering if approaches like that work better at the bookstore where there’s a feeling of more safety for a woman than out on the street. Perhaps I need to tone it down a little for street approaches.

List of All My Pick Up Approaches