You are serving yourself a self-fulfilling prophecy by having this outlook and believing these negative thoughts about yourself. Getting to the place you want to get to, is not about doing some parlor tricks or recited routines, it is about building a better you. It's about BEING the man, not acting like some people tell you you should act.
First you must realize that the primary goal of your mind is to protect you and guarantee survival for you. To do this it keeps you in your comfort zone where you are most safe. If you have always been shy, anti-social, unfriendly, then your subconscious mind will KEEP you that way because it knows that you are safe within that role you have built for yourself. The only way to change this, is by a complete conscious turn around. Your subconscious mind has to see, as it were, that you are putting energy, effort, and engagement into the process of becoming more social. This means that you have to put forth some initiative to change, believe in it, and be confident to step out of your comfort zone.
Change is possible. You can achieve it. You will become the person that you put conscious effort towards reaching.
Firstly you need to be doing this for you, and not for any sort of validation from others. If you are doing this to portray an image that you deeply aren't even that comfortable with, then it will be damaging and most likely less successful. You have to be comfortable with yourself to the point where you don't care about people opinions of you, but you still enjoy their company none-the-less. You are social but not socially motivated.
If you have already been established in the role of the anti-social loser by people you hang out with, then perhaps find a new group or other people that have not categorized you yet, and spend time interacting with them. Your low self esteem will undoubtedly have placed you in a position of submission, at the bottom of the totem pole. Because of this, whatever role the more dominant members (or alpha male, using evolutionary psychology) perceive you as, you will fulfill. Because of this I really recommend finding new friends.
You must change your internal thought patterns, to change your external representation. Perception is projection. Perceive yourself as a fun, amiable, and attractive person, and you will project that towards the world. Immediately catch yourself on ANY negative thought and tear it down instantly. Right now in your physiology, your subconscious wants to keep you in your safe comfort zone and will RESIST change. It will look for evidence to support the beliefs you already have instilled in yourself to prove the point that you are a depressed loser. "What the thinker thinks, the prover proves." You must change those self limiting beliefs you have of yourself and in doing so your subconscious will find evidence to support your new persona as being a great guy.
This was a long post, but you know, I could probably write ten of these and go on and on about it. I also am 20, also do not have a money problem, also in a university, and until about a year ago I was also in just about the same social place that you are now. I wish I had someone helping me out like this back in highschool, and so if you have any questions I will gladly answer.
CHAT