No matter how many lays I get, how many girls I make cum over and over again, I still feel as unsecured as before taking the pill when I go out. From what I've read people tend to be pretty confident after 20-30 lays with different chicks, but I've passed that milestone a while ago and I still feel insecure.

I lift harder than ever, my diet has been in check for more than a year now, I'm reading a lot, took up programming and I stashed some money so I can work on myself for the next two years without needing to get a job. And yet, I can't internalise all this. I feel weak, I feel like any dude I go out with is better than me. So I fake it, it works, but I'd very much like it to stop being fake. Any pointers?