Rahx - I am a fellow nerd and a weeaboo, I'm also someone who hasn't had a lot of success with women, and I also suffer from low self esteem. But I have still managed a few long-term relationships... So I'll try my hand at giving you advice different from the "just call an escort" or "just bone a fat chick" (even though I like chubby women, I've dated more thin/average women than chubby/fat/obese!):
It's definitely a numbers game. I went out with probably 50 girls from OKCupid before I found my last LTR. Try emailing lots of different women with different personality types, different interests, get out of your comfort zone. Not necessarily date an ugly girl, or a fat girl, but if one of those happen to be interested in you, don't immediately reject them.
Take the time to get to know the people you go out with. Ask them open-ended questions. Let them speak, people love talking about themselves. But also have a bit of a backbone and don't let anyone walk all over you.
Read "How To Win Friends And Influence People". The Dale Carnegie Course was offered at my last job and I found it really helped me with public speaking, conflict resolution, and building interpersonal relationships with others.
Don't be so focused on the end-goal of getting into a relationship (or losing your v-card). Think of going on a date as a chance to get to know someone new, to try a new activity or restaurant, to learn about something you may not have had any knowledge before. Not like an interview or a western RPG dialogue flowchart to try and get them into bed.
And stay positive. Believe me, this is really tough to do. I've been extremely depressed these past few days due to the combined factor of my job and woman situation and all the rejections I've gotten from both avenues lately. But failure and rejection are a fact of life, and you may not always get the resolution you need. You just have to either self-reflect to try and figure out what you did wrong, or just drop it and continue playing the numbers game.
