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pwno comments on Teachable Rationality Skills - Less Wrong
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Another way to build up social confidence might be to repeatedly get rejected by asking lots of extremely attractive people out on dates. The goal here is to numb yourself to the emotional costs of rejection through repeated exposure.
Unless the rejection is accompanied by occasional successes, this may be a good way to lower your self-esteem. The trick is learning to accept rejection - using each opportunity to succeed and learning from each failed attempt.