A big problem that I have with my escalation is that I don't really advance after meeting up with a person for the first time. We usually have a a cool conversation and getting her contact to stay in touch (most of the times because of school).

I don't know how to explain this but I don't really know the level on which a person that I have recently met starts being more than a friend. Maybe this is because during my high school years I was meeting up and hanging out a lot of people (80% girls) and did not recognize the difference between talking as friends and as someone who is interested in me. Even when i had all the girls, they used to be the ones to hit on me and my friends would tell me that I am blind that I don't see that they want to have something more. Even now I can't distinguish who wants something more, who likes me from the girls that I meet. And this makes me confused. I somehow expect that there is a yes or a no when someone likes you, but I guess everything is relative and in the dating world there is a lot of in between.

Basically, after I meet them and let them dry out by not texting them, the next time when I see them I act like nothing happened and behave like a friend. I don't know why I am doing this. I start doubting and I also lose interest in them mostly because of some physical feature (teeth, weight). She has to make me knock off my shoes and not stop thinking about her so that I stay interested.

I can also say that I can't recognize when I should ask her for a date. I have kinda forgotten how to date and when to go for the kiss etc as I have been in a dry spell for many years now and I fear I will make the date bad or I will be awkward not knowing what to do when.

All my friends are saying to act normal and play chill, that the girl will come once I do not stress about it. But because of the dry spell I do stress about it.

Any comments, suggestions would be great. I wish I can discuss this with someone. I have talked this to my friends and a therapist but I am still in the same spot. I believe I have a lot of respect towards them and somehow don't want to step some boundaries and make them feel bad, so I stay put.