ThatZealousOne
I think it is really good of you to help out your family. I think it speaks volumes for the type of person you are.
I want to suggest a couple of things and I want you to try the least threatening.
1) Just begin smiling and looking people in the eye and saying hi whenever you pass them in the halls at school or when you first get into work. Make eye contact if you can and say a simple hello. Derogatory thoughts about yourself are not allowed only things like, "well they didn't see me" or "they must have been deep in thought" "perhaps thay are having a bad day" etc. If they don't respond to your ehllo.
2) pick a class you either really like, or a class you are having a bunch of trouble with and find someone who you wish to help you, or someone you could study with, or someone you think you could help with a problem or any other reason you can think of or just pick the last class of the day. Don't necessarily pick a female and don't necessarily pick just one person either, (for a group could be better and less uncomfortable) and say something like "whew! what a day/speech/assignment/etc.! I think I need some coffee, care to join me?"
On either of the above I always use the salesman's rule that one sale out of evey ten contacts is excellent. I state this because I don't want you to give up. However I don't want you to expect anything, either. If you are doing the hello thing the only thing you are concerned with is finding eye contact if you can and being able to say hello, if you get any response at all consider it a pleasant surprise. With coffe, you are only trying to practice making contact with someone, that is the goal, whether they say yes or no is secondary. No derogatory thoughts with either, no failure - if you manage to say hi or ask someone out for coffee that is a your goal and success regardless of the response. For 99% of the time a negative response has more to do with the other person than anything about you.
Let me know what you think.