Well, you're definately not the ugliest guy I've seen in my life. Not at all. I've seen guys with puss running down their forehead. YUCK! You would probably get around a 4/4.5 in my book (which isn't bad since very few people get really high grades from me

). That would be the number I'd give a regular guy.
No job and I'm enrolled in Computer Science at a 2000 student university whose primary major is education.
An all boys school or something? Cause what you need is a female
friend. That will do wonders for you, really. I've seen it happen. If you spend some time with girls you'll get more confident.
But once I do that, there is no way in hell that I could ask them out, hence why I've never been on a date
Sorry to say this, but for most girls this is a real turn-off. Confidence is an absolute
must if the guy wants to have even a shadow of a chance.
I've never been the poster child for confidence, I'm not even in the finest of fine print at the bottom
This is really something you need to work on. The best way is to socialize more. Go to parties (where girls are actually present

). meet new people. In time you'll feel more comfortable.
Really, the hardest part is taking the first step. Because once you take it, there is no turning back.
That's easier said than done when 100% of the people in an area evac or move to points of rapid egress when I show up.
If that's the case, you need to better your image, the way people see you is very important (though this only shows the shallowness of the Human race).
First of all, your hair. Go to a barber shop and ask them to do something 'different'. You can always bring someone with you so you can ask them how it looks as well.
Second of all, dress more casual and not so 'up-tight' unless you have to. Don't wear ties unless it's some formal event. Simple blouse and jeans work just fine. If you don't know what to buy ask if a friend can help you pick out some new clothes (or ask the store clerk, they usually know what's 'in' and whats not).
But really, looks mean
VERY little if it really *clicks*. I've seen guys with 3 centimeter boils on their forehead with girls. All because they got the confidence to make that first step. If you do get together with a girl, she'll probably be more interested in who you are then what you look like. Looks are just for first impressions.
Ow, and don't try and go for the 'cheerleader'-types because they are uptight, care about nothing other then money and have about as much emotional substance as plankton.