I used to be shy. Not painfully, but always reluctant to talk to other people in social functions, I always used to stick with my mates. Then I started thinking what it was like for other people. How would they feel sat across from someone who'd rather stare at the tablecloth than make conversation.
I went to a friends wedding a few years back and all my mates went outside to get stoned, and I was there with my pint clinging to the edges of the room, looking at all these other people having fun on the dancefloor and chatting, and I got a bit jealous.
Then I saw a dozen other people dotted round the edge of the room, holding a glass of wine, by themselves, obviously wishing someone would come and talk to them, but too awkward to just walk up to someone and start a conversation. And I realised - what have I got to lose? Really. If I bore them, then I wouldn't have been mates with them anyway. If they bore me, I politely finish the conversation and move on. And if we get on, then cool.
And the worst that happens is that they don't like me. They already didn't like me because they'd never met me. So no change in the grand scheme of things. And if they don't like me, sod 'em.
Now it's difficult to get me to shut up. I realised that I can make myself believe I'm as interesting, or more interesting, than other people. And I love listening to them. Just ask questions, everyone loves talking about themselves. Or have a fall back story to tell. If theres chemistry and you feel comfortable with each other, then the words will just fall out of you