moridinamael comments on Harry Potter and the Methods of Rationality discussion thread, part 21, chapters 91 & 92 - Less Wrong
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Tom Riddle in canon was described as a classic charming psychopath, while the Defense Professor seems to be genuinely icy and blind to others' internal states. He even verbalizes this a few times, e.g. "I don't have the knack." So either HPMOR!Riddle was actually not charming but instead vastly more intelligent in a cold, calculating way, or the Monroe/Quirrell persona is supposed to be outwardly cold and obtuse while still secretly possessing insight, or this fragment of Riddle's soul has lost whatever insight or ability that formerly made him charming, or something I haven't thought of.
Quirrel tells Harry that they share an ability to "become" whoever they pretend to be. We even see this when Quirrel pretends to be someone else to the Healer after the Azkaban breakout. It would be very odd if Quirrel were able to do this and not have any insight into how people's emotions feel like from the inside. I believe that Quirrel knows perfectly well how emotions work; the icy exterior is just a role he plays.
I don't think Quirrell's model of emotions can be all that refined, since he seems to have repeatedly and legitimately mismodelled both Harry ("yes, I actually do care about people even if I don't relate to them, I don't want to be a Dark Lord,") and Hermione ("You know, a shadowy figure in a hooded cloak is really not the most trustworthy messenger.")
Obligatory protest that we don't know for certain Mr. Hat-and-Cloak is Quirrell.
The way I interpreted that, he thought that if he first showed up looking innocent and good, she would have suspected that the outside was a sham. But after she revealed that she really doesn't think that outsides are always deceptive, he changed his modeling.
Though that would still mean that he mismodeled her, yes.
My thoughts on the mismodelling* of Harry are much more speculative.
I don't think that Quirrel would keep that part of his guise up once the fate of the very stars in heaven is on the table.
Quirrell == Voldemort. This does not imply that Voldemort == Riddle. Dumbledore at least thinks that Voldemort was Tom Riddle, but consider the possibility that Dumbledore is wrong about this. Remember Voldemort really doesn't look very human at all, and could be almost anyone. Maybe Riddle was misdirection.
I know someone with Asbergers who manages to be very charming because he learnt social rules.
You don't need empathy to charm people.
Aspergers. (I've occasionally heard "Ass burgers" used as an insult. No 'b'!)
That's a South Park reference. Insulting, yes.
Yes. Psychopaths are a prime example.