Today I made small talk (to various degrees) with strangers on the street as a challenge.

The first person was a skinny girl (I guess on her 20s). Her hair was dyed blond and she was very shy. Painfully so. Maybe I was creeping her out. I asked her about her opinion on having pet turtles. That lead to a conversation but I felt that I was talking at her instead of with her. I noticed that I was so busy trying to think of the next thing to say that I didn't listen to what she was saying or was interested in her for that matter.

Then I came home and a cozy feeling embraced me. It was trying to coerce me to stay put and send my previous socialization effort into a sea of regret. However I stood my ground and went out again, however uncomfortable and unwilling I was.

As soon as I came out I spotted a gay couple walking towards me. I noticed one of them was wearing shorts even though the weather was not shorts friendly by any means. I said: 'that can't be healthy, its kinda cold outside' in a cranky/whiny voice. It just made so much sense when it came to my mind, but as I write it down it sounds like an offense. The couple gave me an aristocratic look and kept walking as if I was a light post.

I was still thinking about my failure when a couple girls came into my field of vision. They were sitting at some steps in front of a building. For some reason the weather topic was stuck to my mind like goo in asphalt: 'wow, its reaaaally nice outside' I said as I walked by. I was trying to sound sarcastic but the line ended in a cranky tone... Again. One of them made eye contact with me and all I could see was discomfort. The look said it all. Three failures out of five.

The next one was not that bad. There was a mother strolling her baby and I greeted the baby with a graceful 'whats up' (which I've obviously mastered since its the most generic thing one can say). The mom seemed pleased and told the baby to say hi back, which of course was a generic answer since the baby couldn't talk.

Lastly, there was a delivery guy in front of my building door and I asked him if he wanted to come in or keep waiting outside. Turns out he couldn't speak English and he kept saying agreeing while nodding. I decided to count this one as an approach since I was honestly a little bit discouraged about the previous attempts.

How many of you guys have tried something like this? Does it get better eventually?