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It's so much worse to regret something you never did. It's often worth running through your fears to their logical conclusion to help disperse them. One footnote - if life has taught me anything it's to trust the shy people. Popularity means a lot of people like you a bit, you have broad appeal. But who wants broad appeal? Interesting people are always a bit niche. Remember what Steven Patrick Morrissey said: "It takes guts to be gentle and kind.".
