I think there's a fine line between getting out of your comfort zone and doing things that deep down DO make you uncomfortable. For example, I always hated parties and people that go to parties regularly; if I tried to "get out of my comfort zone" and try and get involved too, I wouldn't really be achieving anything more than give me headaches and tiring myself out. If the case was "I've always wanted to go to parties but I'm scared of it (for whatever reason)" then it's a MUST to beat that fear and then see if it's for you or not. I know some people that are pretty deeply disgusted with relationships due to prior experiences and sightings, so you can't really ask for people like that to go and date someone.
I kinda had your issue some years back, so I'll tell you what worked for me: everytime I'm afraid to speak up or do something that I think its risky or embarassing in case of failing, I force myself to say it and then make sure to remember that moment and what happened afterwards. After some of those cases, you realize that whether you do/say it or not, most of the time, at the end of the day it had no real repercussions, and all that anxiety and doubt you had prior might as well been for naught. After some months you start having more confidence in saying or asking whatever you mean to. I was like you like two years back but now I'm gettin all the hoes, trust me
Don't mean to say you don't try, because I'm not you and can't know how much effort you put into this, but you can improve, and it seems you are serious on this. Don't give up. Blessings.