This was the first time I approached a woman on the street and it showed – it didn’t go that well. But instead of feeling down, I’m actually feeling determined to improve myself in this venue.

I was out on my daily pick up practice walk and as I passed a bus stop I noticed an attractive woman waiting inside the bus shelter. She was putting her hair in a ponytail while waiting for the bus and she was the only one waiting at the bus stop. As I passed her, we locked eyes – perhaps a little too long. I hesitated – I should have just gone for it right there but I continued walking and didn’t approach her.

About half a mile after I passed her I decided to go back and approach her. As I’m heading back I saw a woman walking on the other side of the street so I cross over so I can say hi to her. But the woman crosses over the street right after I cross over to her side of the street (did she get scared that I crossed over to her side?) Then I see a woman walking her dog and I was going to say hello to her. I was even going to stop and talk to her (once she got closer so I can tell if she was attractive or not) but she started heading off in another direction. Damn it – I began to lose my confidence.

I was getting closer and closer to the original woman at the bus stop. She was now standing outside the bus shelter still waiting for the bus. As I got within conversation distance I stopped close to the bus shelter and just said “Hi” to her.

She didn’t say a word but just stared at me – maybe in that “Oh my god, what’s he going to do?” type of way.

I said, “Hi” again and she continues to just stares at me but now with a “What do you want?” expression.

I say, “How are you?”

She doesn’t say a word but perhaps moves her chin an inch.

I finally just say, “I’m just saying hello.”

She’s now sort of glares at me – like in a “What the hell do you think you’re doing?” type of way. In a nutshell – she’s clearly not interested in interacting.

So I decide to move on and continue walking. I shake my head a little at this woman’s intense reaction. Maybe she was having a bad day. It reminded me of thirteenth pick up attempt where the woman completely ignored me at the coffee shop.

I tried to shake off the sting from her rejection by continuing with my walk and saying hello to people, which helped. I feel I need to improve my street approaches.

Things I Learned

  • Staring at women is not cool. It tends to scare them and put them on the defensive. When I was passing her by and she saw me through the bus shelter glass, I think I stared at her too long. Who knows – maybe I looked like some hungry puppy or something. Not the impression I want to have on her. I think that made her more defensive and cold to my approach when I came back around the second time.
  • Getting completely and utterly rejected by a woman isn’t that big of a deal. Sure, it stung a little and I felt like she totally misjudged me and my intentions but I also thought she was a cold fish that wasn’t open to sharing a new experience. Her loss – she missed out on a fun interaction.

List of All My Pick Up Approaches