What will happen if I challange the status quo (relationships)

Ok, just a little bit about my situation. I have always been “that guy.” That guy who never had a date. That guy who women know regard as “just there.” That guy who never talks about women. I am not a nerd. I have friends and a social life. All my friends are all successful with women.

Now I have recently been sorta successful online. I am talking to a few pretty women, and I know they have some interest. I want to chill with them, but somethings holding me back.

I have a feeling that I must continue to fulfill my role in society no matter how negative it is for me as an individual, it’s just who I am, I have always been “that guy.” What will happen if I oppose the status quo and start dating? Will I be questioned by my friends about my new motives (this worries me)? Should I keep my actions secrete? Why do I have these fucking annoying obsessive thoughts that are holding me back?

Sorry about the rants, I just don’t have the cash for a therapist right now so I thought this would be the next best thing. I am not asking people to feel sorry for me, I just want advice