Probably silly, but thinking about this I realize I get away with a lot of shyness by being female and working in a mostly-male environment- maybe try a mostly-female job/class/hobby and let them come to you and turn your shyness into a bit of a challenge for them? Activities in general help- give you time to be around/interacting with people without having to justify why you're there talking to them or feel like it is over if there's a pause. Then, if you're really wanting a challege, maybe meet random people for dinner/drinks/etc through a dating website or something- knowing that it is a very unpredictable situation so you have to go in with no expectations but with the belief that you might have a great interaction as well. (Just for the record my experiences have never been nearly as awkward/bad as I have feared; and I met this awesome introverted guy thru craigslist- we met up and started talking and quickly forgot our nervousness instead finding someone to totally understand each other- a few years ago I never would've gone and met some random person, but I am so so glad that I did)
|