I'm not a looker, but I'm charming.... how do I meet people outside school?

A male age 30-35, anonymous writes:

I wanna meet people outside my school but i don't how, im kinda shy around new people until i get to know them a bit then i loosen up, but i dont feel too comfortable walking over to people and making conversation. is there anyway to boost my confidence i bit more? im not good looking so i cant really use that to my advantage but i suppose i am kinda charming in a way.

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A reader, anonymous, writes (18 November 2008):

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