I hate to be sound cruel, but sometimes you have to lay your soul out to bear to someone and hope they don't crush you. I think it is tough but the only way to make that connection. I remember in high school going out a couple times with this very pretty Hispanic girl. Remedios was her name. We weren't bf/gf, but that's what I wanted. We went on a couple of dates, but nothing ever happened and then I asked for me and was rejected. It sucks to be rejected, and personally I find it very gut wrenching. I used to have really bad self esteem though. It sucks for a while but it gets better. Just because someone doesn't like you doesn't mean you are ugly or an awful person. It just means they don't want a relationship, had a messed up one recently or have a bad one they are hiding. The point I'm trying to make is you have to keep pursuing women for it to happen. I don't know when the last time you tried to date someone, but I can imagine it would be easier dating a 24 year old than a 19 year old. My memories of being around 19 girls were they were self centered and didn't know what they wanted. Maybe that was just college freshmen though, i dunno.

I wouldn't count the hookers as a necessarily bad thing. I wouldn't brag about it to future gf's, but you did learn how to please a women. It raised your self esteem and put things in perspective. Who is better to tell you about sex, than someone who has it on a daily basis? I've only had sex with one person and my first few attempts were pretty abysmal. I had do idea what I was doing. My wife had a couple bf's before me and I learned what to do. I think when you get over your fear of rejection, being able to have good sex will be a big bonus for you.

Your not the first guy to pay for sex. I wouldn't beat yourself up to bad over it. I think therapy could help you deal with your fear of rejection. If it makes you feel better, you only have to be rejected until someone says yes, then you are home free.