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If I wrote a letter to a singer in this case, not extremely famous like Pink, asking if perhaps they could give me a few tips on how to get over my shyness, do you think they'll reply?

Thanks

Well, I once wrote to an actress, not very famous, that I wanted to be one, too, and she sent me a letter where she adviced me not to get discouraged with my shyness. So go for it, you have nothing to lose, the worst they can do is not to give you any tips .

Some will make personal replies (you'll see that a number of people here like to send questionnaires) and some don't, it's really up to that individual.

Bit of a random tip, but I've really found that doing social things in small groups to be an non-overwhelming, effective way to deal with social anxiety.