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How can you tell if someone's being nice to get something from you, and being nice just to be nice? I've been a remarkably poor judge of that in the past. I still don't like the idea of using someone for my benefit, even if they're offering, because then I'd be placing myself in that first group.
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The simple answer to this? With practice. Those of us who have experience in socializing learn to see the cues that tell us when we think someone is being genuine or not. The way we learn these cues is by, as Cynthetiq points out, making mistakes.
Yep. You have to put yourself out there and try to connect with people. Sometimes those connections will amount to nothing... sometimes great friendships and sometimes... something negative. I can safely say that the negatives are few and far between and that there is a lot of small talk that happens between putting yourself out there and finding friends.
I should also point out that most people learn this behaviour as kids. You are going through it now so it's a bit tougher because most of the people with whom you are interacting are already adept at their tools of interaction (think Tom Hanks in Big when he attends the Christmas party if that helps).
The most important thing, and I know this is probably hard for you, is to just let go. Chat with these people as you would chat with your students. Be the person you are here. Don't worry if you make a mistake. Mistakes are an opportunity to learn (make it a mantra).
What the worst thing that could happen? Someone will laugh? Most times they will think they are laughing with you because they will assume you know the social cue you just tripped over... brush it off and move on. Better yet, learn to laugh at yourself.
The way I learned to cope with my shyness was to do the following... sit back, gage the situation and then jump in with both feet (it's the same advice we give people who are new to Internet forums like the TFP).
Be yourself. Don't over analyze.