Kingreaper comments on Polyhacking - Less Wrong
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If they're asking, they deserve to be told.
If they don't want to know, they shouldn't ask. Lying to someone "for their own good" is, to me, one of the most disgusting concepts in existence.
I've been lied to "for my own good" several times. And every single time, all it really did was allow the person lying to me to feel good about themselves, while simultaneously screwing me over.
If they're asking, it's often not because they actually want to know, but as a way of telling the other person off for having the wrong opinion. Telling them puts everyone in an extremely uncomfortable position. If I wanted to pass on such information to someone, I'd do so anonymously.
To illustrate, I'll go through some likely results of telling someone each of these things Vs. not telling them.
They are now aware that their weight is a major reason for lack of success. This is an extra incentive to lose weight. In addition, it's possible they weren't even conscious of how overweight they were previously. So, they gain health benefits.
They now know to be on the look out for either smaller partners, or partners who show signs of a crushing fetish, as opposed to continuing to ask large people who will turn them down.
You may need to give more explanation on this one; because it's likely that there's some specific part of their behaviour that's a problem. However, at least they are now aware that they are giving off vibes of desperation, and can try and change that (giving them more self-confidence, because they now know that the problem isn't something innate)
They get to feel morally superior to you.
Provided you are willing to explain why you find their conversation boring, this is helpful. Seriously, I'm friends with a lot of aspergics*, and every time I explain to one of them "you're being boring, the problem is that you are doing X" they have henceforth put effort into avoiding doing X, which has increased their success in socialising.
*(I suspect this is because I'm a borderline case myself, and therefore often end up acting as a "translator" between them and NTs)
They don't know why they were rejected; and likely find themselves wondering whether they'll ever be able to be successful, making them feel increasingly desperate and despondent about their chances with each rejection.
While the first few rejecters may successfully prevent this by using "it's not you it's me" type lines, it will soon become clear to the rejectee that these are, in fact, often lies.
This one may not be as good as you think. Fat people are generally told repeatedly that they're fat.
The risks of being fat are generally wildly overestimated.
I've read a moderate number of accounts by fat people who found that their romantic success improved when they stopped pre-rejecting themselves.
From experience: this can lead to resonant doubt/panic attacks. It kinda sucks.
Good point. It can result in a kill-or-cure situation, either they take it as "I can solve this" and gain confidence, or that they can't, and lose even more.
There were a few articles here on the limited introspection humans in general have. I assume they have less so for others and also are not necessarily able to express their reasons well enough to be understood.
My guess is that Aspergers (or generally people with internalized nonstandard interaction modes) have the best chance to get useful information from people who are also off, but less so.
Questioning a person about why they feel a certain way about you is weird in its own regard. And there is no safe way to communicate about communication.