So today I was out with a girl for a first date. Near the end we walked for a bit and I dropped her off at the streetcar. There were only 2 times that I found myself not being in the moment and thinking "what should I do?" When I was thinking about taking her hand while we were walking and when I was thinking about kissing her when she got on the streetcar.

I sent her a text a minute later saying I should have kissed her (I figured if I didn't I wouldn't see her again anyway) and she said she was just thinking the exact same thing. Point is I did really good right up until I got in my own head and second guessed myself (ability, attractiveness, etc). She really liked me and just needed me to take that leap myself.

Not sure if it will but I really hope that helps someone else. I'm going out working on my own anxiety/self-consciousness every week now and I know how hard it can be.

Amazing story Operator. It's such a waste of time and girls and opportunities that come past us and we miss them. I had a girl once tell why did you wait so long before you kissed me. And I thought all along I wasn't good enough for her. Just curious what exactly did you text her about kissing ?

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"Experience is the teacher of all things"

I usually don't like sharing specific details just incase (and so my stuff doesn't get recycled 100,000 times) but I told her I was still waiting for my streetcar and that it was kind of random but I wondered what the first thing she would do with a time machine would be (It fits me because I sometimes do this kind of thing to start role-play or interesting conversations). She had a cool response. I told her I'd go back in time and kiss her right before she got on that streetcar. Came up with it on the spot and she liked it lol.

I DO have some natural game but only when I'm not afraid to use it

Haah, spot on! live in the moment, nice!