jdgalt comments on Tell Culture - Less Wrong
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The big problem with habitually "telling" is that you just about need to already be in an intimate relationship with the person you Tell before you do it more than once or twice. Otherwise you will be dismissed as either a bore or a wimp.
It varies. I do a lot of it within a community that appreciates me as a kind of quirky guy who talks a lot about his own internal mental state, for example.