Believe me, I know just how you feel. I have certainly improved over the years but nowhere near overcoming it.
When I was a child, I barely talked to anyone. I would slowly open up to friends and other than that, I only talked to my family. As I've gotten older, the thing that has helped most is work. When I was in college, I worked in retail and absolutely had to talk to people almost constantly. Even after years of that and then going on the professional world where I have to talk to clients and coworkers, I still am much more outgoing at work than elsewhere. It's almost like I have two sides of me... I talk to anyone I need to at work and have been complimented on my way of handling people many times but in my personal life, I'm still pretty shy.
Of course I'm loud and silly arounf close friends but it takes a while to get there. I'm always the quiet one in a group and a lot of times I don't think people even realize who I am at meets. Another thing, I'm terrible at calling people. Just as you mentioned overanalyzing everything, I do that as well. I second guess calling people and being more social because I don't know if people want to hear from me.
But anyways.... as I said, the biggest help was work. Also with meeting people in social situations, stick with what you know so it's easier to talk to people. For example, if I went to an event centered around say... wine tasting... I'd be clueless and probably not talk to a single person. But I go to car meets because I can talk to people about cars. Go out a few times and just stop and take a look, compliment the owners of cars and before you know it, you'll have conversations. It's gradual but you have to try.
Good luck.
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Originally Posted by JennB
Another case Of white collar "wannabee" talking down on retail employees... 
