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Jack comments on Rationality Lessons Learned from Irrational Adventures in Romance - Less Wrong
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I'm pretty neurotypical by Less Wrong standards and I don't see any tactless comments here.
How about joking off-handedly over an highly embarrassing, ill-judged thing that a stranger disclosed about their past?
I can see how they would be tactless in other settings and contexts. For instance, if Luke wasn't so clearly disassociating his current self from the person who did this embarrassing thing. If he hadn't brought it up. If it wasn't the kind of thing a lot of people here would totally do. If he didn't work under Crocker's. If this wasn't the internet. If he wasn't very high status in this group, etc...
ETA: I think you're actually missing a number of the relevant subcultural norms and situational features that make this kind of joking okay.
Indeed, yet the sheer social horror of this action (showing his ex that document), to me, greatly outweighs all the reasons you listed. Me, once I'd have come to my senses way after committing a blunder of such intensity, I'd likely need a therapist to resolve it, or else would have buried the experience as deep as possible.
Kevin and Luke aren't strangers.
There are quite a few playful (to them) or inconsiderate (to me - and quite possibly to Luke himself, though he would understandably not admit it publicly for fear of pushing them away) comments from different people above.