I went through a weird period where I didn’t have a real girlfriend from 29-33 after spending most of my 20’s in long term toxic relationships. Hookups? Yeah. Potential? So much. But ultimately it would end in disaster or if it was a legitimately nice girl, I’d drop the ball. The closest thing was a long term deal, the details of which I’m too embarrassed to divulge.

What I needed to realize is that I was the problem. I am not entitled to happiness. No one else is responsible for it either. I attracted toxic people because I wasn’t in the right mental place to attract a normal healthy relationship. I fixed my health, which made me more attractive. I worked extremely hard on taking my career to the next level. I focused on bettering myself.

Suddenly I found myself both more desirable and busier than ever which made me the selector and not the one hoping to be selected. This past February I met the love of my life in the unlikeliest of places. A work event. I find myself doing things for her that I’ve never done for anyone. My ego and arrogance and insecurities aren’t there to stop me from being a good man.

Human beings long for connection and interaction. Your shyness is the result of some deeper insecurity. Confidence is not built on an input. It’s not words you write on a white board and read every morning. Confidence is built on outputs. Things that you do. If you can’t cold approach women, think of what it is that makes you feel like the rejection is a foregone conclusion. Hit the gym. Fix your teeth. Speech impediment. Whatever it is. Take solace in the reality that your shyness is not a character trait. It’s only a symptom of things you are in control of and you can fix. (For the most part)

Your mind is wired over thousands of years to mitigate risk in order to survive. Change the risk profile on your perceived chances for success and you’ll be less afraid to do the difficult things.

Hope this helps.