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Document comments on A less wrong way to talk about the arts? - Less Wrong
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I don't tend to do this sort of thing - at least not on subjects that I don't have some relative expertise in. When the other person can keep up and doesn't feel uncomfortable about it, they've usually already thought the thought if it's not something I am particularly knowledgeable about. A third option is intentionally framing a discussion on some fairly trivial subject as an argument, which I dislike strongly.
A fun trick is to say things that assume the other person has already thought the thought. If they don't understand instantly you can explain in a more natural and less adversarial way, and if they get it I like it better than just saying something and them agreeing.
"Say things that assume the other person has already thought the thought" generated a cached response in my brain of "Are you joking? I hate it when my mouth does that!", and now I'm not sure why. I could try to list possible ways it could go wrong, but that probably wouldn't help much. It's also possible that I'm just associating it with similar beliefs I used to have that were bad.
I wouldn't say it's a general-purpose conversational gambit, but it's one of the things I do instead of talking about thoughts in order to be challenging. I prefer the challenge to be implicit and the fun to be explicit.