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ChrisHallquist comments on White Lies - Less Wrong
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Boy, I sure wouldn't want to date a person like this (your girlfriend-at-the-time). She asked for your opinion; pressed you to actually give it, thus communicating (by any reasonable measure) that she actually wanted your opinion; and then, when you gave it honestly, was unhappy about it? That's horrible.
I don't think I'd ever willingly choose to be close to someone to whom I'd ever regret not lying in response to being asked for my opinion. The thought of living like that, living with the knowledge that honest communication is basically impossible because any time the person asks me (and presses me) about my opinion, I have to consider the possibility that what they actually want is lies — that this person prefers lies both to truths and to no comment — repulses me.
As best I can tell, "people who sometimes ask questions they might not want to hear the answer to" are a large majority of the population. "Does this dress make me look fat" is a cliche put-you-on-the-spot question for a reason.
Sometimes is an important word here. Too often, and it might be an issue, but it's not like this was a regular occurrence with her. (A big THANK YOU here to Pablo and hyporational for noticing they shouldn't be making too many assumptions based on one anecdote.)
Now, another approach is to exclusively date people who value total honesty at all times. But (1) there are other qualities I value more in a mate and (2) I suspect such openness to "total honesty at all time" tends to correlate with being social inept and overly honest even with people who don't want that, qualities I'd like to avoid.
(BTW, I usually answer that with "you looked better in that other one", so I don't offend her but I still help her choose flattering clothes.)
To reiterate a point I have made several times in this post's comments:
"Valuing total honesty at all times" and "refraining from pressing someone for an honest answer when what you actually want is a lie" are two very different things.
Correspondingly, being totally honest at all times, unprompted, is not the same as being honest when specifically pressed for an honest answer.
I try to restrict my circle of friends to people who do not ask precisely such put-you-on-the-spot questions. That, among other policies and attitudes, makes my circle of friends small.
Or, to put it another way: people worth being friends with are rare. And those are the only people I want to be friends with.
You're misunderstanding the message.
"Does this dress make me look fat?" is not really a question. It's a request for a compliment.
If I may engage in gender generalization for a moment, men usually understand words literally. This annoys women to no end as they often prefer to communicate on the implication level and the actual words uttered don't matter much.
In a sense, yes. But less-cliche questions sometimes get used the same way, and you have to be on guard with that.
(You can argue that giving the expected responses to such questions isn't technically lying, but that seems like semantic hair-splitting to me.)