OP,
I don't know what you look like but looks wise if you are clean, have good dental practices, bother to cut your hair (heck maybe even style it), and put some clothes that look like you've put at least some thought into your appearance, many women will be interested in learning about your personality.
Have you bothered to do those things? If not, what are you waiting for, I am telling you it will make a difference because it makes a difference.
Second, right now no woman in her right mind would be attracted to your personality because you're too down on yourself. Get hobbies, get excited about anything you're genuinely interested in even if it's star trek **** it doesn't matter women (hell people) just want to see you get excited about something and enjoy life, it's ****ing attractive man!
Last, you seem to have very negative connations for hookers. I think it could be fun to drop some cash on a hottie porn queen or something, might be a good laugh to do something like that. I picked up some hookers the hard way (looks and personality) in Latin America. They were OK chicks man, we had fun and I don't regret having met them. I know a chick that got a hooker for 3 way with her bf too. It's all good.