Shyness Support Group
Shyness is a feeling of insecurity that certain people experience while being among others, talking with others, asking favors of others, etc. The initial cause of shyness can vary. Scientists have located some genetic data that supports the hypothesis that shyness is at least partially genetic.
I like to ask people about what they are doing over the weekend, what they did over the holidays etc. This can give you some information about their family, interests etc, and this gives you more things to talk about.
Generally people like to talk about themselves, so if you can ask people about their children, or a special interest of theirs. From this, you may find interests in common you can talk about.
The weather is also a good topic, even if it's horribly cliched.
You could ask people about movies they have seen, or ask if they saw a particular programme on TV. Light entertainment programmes would probably be a better place to start than current affairs, until you have a better idea of the person's opinions.
See what sort of questions the other people/person ask you, if they ask about your job etc, ask them about theirs.
I find it difficult to start up (and continue) conversations with people I don't know so well, but I'm going to keep practising.
Good luck!