Hi,

Beginning last year, I begun challenging myself to rid, if not
reduce my shyness. This is what I'm doing and accomplished so
far.

1) I always hang around where there are the most people as
possible in order to increase the chances of conversations.
(This is not to say that conversations are always most likely to
happen in crowded areas. It's just that I feel more comfortable
speaking to someone in crowded areas). This way I'm more likely
to stumble into someone I know.
For example I only eat in restaurants during the busiest times
and which has the most staff. I try to sit in the busiest
sections. (I use the word 'try' because often time single
customers aren't permitted to sit in those areas).
The thing I hate is walking in and sitting alone. In restaurants
where the minimum number sitting at a table is two, I have
tendency to be placed in a corner. And some people glance at me
thinking I'm waiting for a friend or something.

I hang out close to work to increase the chances of coming
across customers. And it is working. Every day I come across a
few customers to speak to.

3) I changed the way I respond to people. In the past whenever
anyone asks me how I'm doing, my shy usually response would
be "fine" and then I'd walk away! Instead I say, "Great! thanks,
and how are you?" and "How's your day going?"

I force myself to say hi to waiters/tress and people who I've
talked to before. I've noticed every interaction I have help fade
shyness little by little. I found that once I know how to say hi and
respond it's no longer a problem. But problems still occur when a
situation comes up where I don't know what to do.

4) what also helps me is being in a small town (I'll post about this
separately).