I read this 2 and 3 times, so I could further image myself in the OPs situation, and I believe going to that private school has affected him, and began this "domino effect".. I couldn't imagine going to a school without females. I think the OP needs to forget about the women for now, and work on his confidence. Without confidence, you're not gonna get anywhere in life. Women and even 'LIFE' itself can detect a person that lacks confidence. You'll become different altogether with confidence. I was a virgin all the way up until I was 19, then I found this website, and I followed it closely, like my grandmother does the Holy Bible, and I learned.
-I learned that I have to be confident
-I learned to never set myself up to regret anything, 'YOLO' you only live once
-I learned that REJECTION is a very important part of SUCCESS! Scared to approach women? Why? The worst she can do to you is say "no", slap the sh*t out of you, kick you in the n*ts, or laugh... and it doesn't kill you. Go to her just so you can get that REJECTION.. look forward to the REJECTION, play a GAME with REJECTION; it's so fun. Once you do this, you'll notice that you're so calm and natural with approaches to women, almost to the point where you could care less. I used to do this ALL THE TIME.. then they stopped rejecting me.
-I learned to NEVER place women on a pedestal or bow down to them and kiss their ass.. be the way most guys AREN'T.
-I learned to stand my own ground
-I learned that I can walk away from any woman
-I learned self-control
-I learned to rid myself of 'desperation' and 'needy' emotions; I have my heart in check..
-I learned that I have to truly be all about improving myself FOR myself, and not to because I want some girl to let me f*ck her.
-I learned to enjoy being alone, and knowing the difference between being "alone" and being "lonely". When you get married, and you can't get rid of that nagging wife who's always getting on your damn nerves, you'll KILL to be "alone", so you can go do whatever it is that you want to do..
I learned so much from field experience, and not online interactions. I started having girlfriends; i even fell in love once, and got my heart obliterated, which also made me feel like sh*t, but I learned from the experience.. "What doesn't kill you makes you stronger..". I survived, became even more confident, stopped being the nice guy, did things on my own without feeling a need for female accomodation or approval, and I became HAPPY with my life.
When you finally experience the state of TRUE HAPPINESS, thats when your confidence explodes and magnifies by 1,000! I used to be like the OP, until I found confidence. Now I am 27 (28 in a week), no kids, females harass me all the ****ing time, and I'm still on a lifetime journey of self-improvement.. and the best time about it all, I love giving back to this place and to anyone that needs advice.
If I can do it, you can do it too!