Everything really changed near the end of high school.

1) I started talking more 2) I stopped caring what people thought about me 3) I made friends with people who talk to me with respect, and, as guys, are willing to throw in some insults (for fun) and I was able to develop a way of responding with snappy comebacks.

During university, I used my newly found skills to start talking to more people, and made friends with even more people.

I started working in a place where customer service skills and conversation are a requirement of the job; without these skills there was no possible success. There was a huge difference between when I started, and when I quit that job.

One thing that really worked for me when talking to ANYONE, was to start talking to someone using a question about something the other person has. For example, if the person owns a blackberry, ask them "why do you have a blackberry?" Literally any question can work. This helps people to know that you care about them. This must be done consistently with genuine interest to get better and more confident when asking questions. Something else that worked, was a small insult that insults yourself at the same time. For example, if you are both wearing a shirt with squares, you could say "I hate shirts with squares on them" while looking from your own shirt to their shirt. In my experience this makes the person laugh, because they notice youre only joking.

The best thing you can do is start the conversation. Don't worry, as nervous as you are, the other person will appreciate you starting a conversation. This shows people that you are NOT socially awkward and instantly makes them like you more.