I'm someone who's had girlfriends, dated, etc, but I've always been terrified of starting up a conversation with a woman randomly in public. Pretty much everyone I've dated or talked to has always been through situational contexts, like people I met through a group, or co-workers, or classmates, or people that work in a business, etc., that I get to know over time.

It's especially gotten worse for me over the last 2 years because I've gone through some traumatic experiences and my self esteem is at an all-time low.

The other day, I had one of the most pathetic experiences of my life, where a girl was following me around the subway. Like, she walked to where I was on the platform, then walked to where I was on the subway, then was standing behind me on the escalator, very clearly putting herself in my vincity. I still couldn't start up a convo, because I couldn't think of anything to say.

So I decided after how pathetic that was, I'm going to start up a conversation with one woman in public every day, no matter what.

Yesterday was the first day. I was at the park and there was a woman who looked like she was in her 30s who was attractive walking her dog.

Started up a convo...it went pretty much exactly how I was afraid it would. It was a lame, awkward convo. Her dog was wearing some weird clothing so I used that to start up the convo, then asked some more questions about her dog, she asked me a question and I had a bit of a boring answer, then couldn't figure out how where to take the convo and it just died. But the experience taught me some things:

**1) It wasn't a big deal**
Even though the conversation was lame and awkward, it wasn't that bad or embarassing. I'm sure all of us have awkward interactions from time to time, at work, or the store, or wherever. This was just another one. There was nothing special about it. Nothing bad happened - we talked for a couple minutes, then she left. She wasn't horrified, I wasn't humiliated - it was just a bit awkward.

**2) I felt way better after**
I think part of what terrifies me about approaching is that I will feel like it will be a hit to my ego and make me really feel like a loser, bring all my faults to the surface. It was actually the opposite. I felt way better, more relaxed, and more confident after doing it, even though it went poorly.

**3) I now know how to improve**
I have really poor conversational skills at this point in my life and a lot of the time I can't even figure out what I'd say or talk about without some context to spring off of (like we're both part of a group or both co-workers). Now that I've had that convo, I can actually see where I could've improved and where I could've taken the convo. There's a clear path to improve now.

**4) I don't think I'm that far off**
It always seemed like it would be so hard for me to start a convo randomly and get a girl's number. After this convo, I don't think I'm that far off. Definitely far off from wowing someone or really charming them, but if I had asked some more personal/interesting questions that properly escalated the convo, I can see that it's possible I could've gotten a number.

I have a lot of things to improve on, including my style, speaking patterns, overall vibe, etc. But I will continue to talk to at least one woman daily while I work on all those. If you're in the same boat, I encourage you to start today too. Whatever horrible scenario you're conjuring in your head is probably extremely unlikely to happen.