I'm an Asian guy, 19, 5'11, about 170, and below average in the looks department. I've never had a girlfriend, and I'm not too good at talking to girls in general. I am told to be confident and optimistic, but that all seems hard when you look like shit and everyone around you is extremely shallow. Can anyone offer advice for ways to exude confidence and have better social skills around women with an in-depth explanation? (Yes, I plan on being rich, but I don't want to be a 30 year old virgin).

"Can anyone offer advice for ways to exude confidence and have better social skills around women with an in-depth explanation?"
In order to exude confidence you must build confidence. It can't really be faked in any convincing or fulfilling way.
You need to stop thinking with such a negative attitude about your looks and stop focusing on your perceived flaws.
Unlike men, women place a lot of importance on a man's image rather than just his physical features. Fortunately this means any man can significantly improve his outward attractiveness by improving three major things: style/fashion, grooming, fitness. I would recommend you put a significant amount of time in learning and practicing fashion and exercise. Start lifting weight --I'm serious about this. Do it. Improve your grooming as well.
Also try to get a good haircut: http://www.youtube.com/watch?v=_uqe3cvNPYk

The more you improve your physique and your fashion sense, the better you will begin to look and the more confident you will become as a result. Another aspect of improving your outward appearance is with body language --good posture, looking comfortable and relaxed, strong eye contact, etc.

Having said that, please understand that it isn't only looks that spark attraction in a woman. It's ultimately value that they are attracted to. What is value? That's not an easy answer because there are so many things and ways to have value and provide it to others.
Yes looks are a form of value and help and so is money, but what's much more important than looks is how you make a woman feel. This is why confidence, courage, kindness, humor, lack of neediness, playfulness and teasing, having a passion, intelligence and being adventurous are attractive to women. These things are powerful and completely internal characteristics.

The simplest answer to your question on how do you become confident: constantly investing in yourself. This means actively improving your life and lifestyle (travelling, playing sports, learning an instrument, starting a business, following your passion etc), investing in your health and appearance (working out, style/fashion etc.) AND yes, in order to have better social skills you have to invest in socializing (duh). This means going outside your comfort zone and talking to as many people as you can. Obviously this means approaching attractive women, but this also means socializing with other men, making friends, talking to old or ugly people in line, making small talk with employees and many other ways. There is no simple, quick way of improving social skills, just like there is no quick way of losing weight and becoming fit. It's a continuous process that takes time, effort and patience. The more times you approach women, talk to them, try to take things further, the more you will figure out what works and what doesn't. Eventually things will start clicking and your social awareness will improve.

I hope this helps, if you have any other questions just ask.

you can approve your social skills and confidence by approaching and opening as many girls and people as possible. If that has to be paid help at the mall then ok, start with that, maybe 100 a day? Don't you think this would help?

As far as looks goes, what ive seen work for ugly guys is to go for a "look". Like the ugly hardcore rocker, hip-hopster, or EMO slacker. If you can ensconce yourself in some subculture associated image, your casual ugliness will be largely masked and misdirected by the genre. As an Asian guy I think this would be an even more effective plan, as Asians are normally very conforming thus the useful contrast.

The best and simplest way that helped my understand confidence is "comfortable in your own skin"

Don't expect anyone to be comfortable around you if you're not comfortable with yourself.
First, meditate.
Kick your own ass, think of your faults and throw them at yourself. you have to know who you are, what you like, what you want, what you feel. YOU should be known best by YOU.

Next, Reinforce who you are.
You're a man who likes sex. You're a lover who likes making people feel good with nothing in return. You're comfortable with your faults and strengths.
Think of the man you want to be and reinforce it to yourself, over and over until you can freely tell someone else the same without hesitation.

Be who you are to others.
Once you've locked up on the inside, just start a friendly conversation with people, clerks, passerbys, and whoever else. Be interested in who they are and learn about them. easy as that.

(Something I use to reinforce this; everyone has a story, a different way they've lived life. Listen, learn, and take something from it.)

Confidence is not this trophy of achievement, it's simply being secure of yourself as a person.

Oh and Work out. A good body and exercise builds self esteem physiologically and Mentally.