Human Communication is Complicated and Frustrating
One of the consistent problems I've had in both my personal and professional life is that of communicating clearly with others. I have trouble telling what people actually mean when they say or do a certain thing, and my statements are often misunderstood by others. The response is usually some variant of "why are you having so much trouble with this very simple thing?"
Most people learn how to communicate on a largely unconscious level, and they just do what feels right to them in the moment. This lets them communicate well with each other, but makes it hard for them to understand why it might be difficult for someone else who doesn't have that intuitive understanding. They don't realize just how convoluted a system they're following without even thinking about it.
The ladder of social meanings
Imagine a society much like ours, except that people always speak literally. No implicature, no hyperbole.
When someone asks "does this dress make me look fat", they get back a "yes" or "no", and can use that information to decide on what to wear.
People in this society are still subject to normal human emotions, so hearing that they look bad in a dress makes many of the askers sad. Some of the answerers feel sympathetic and don't want to be the cause of the asker's distress. So they start saying "no, it doesn't make you look fat", even if that's not true.
This behavior spreads and becomes normalized. Askers start asking the question not because they want to know the answer, but because they want to know how much the answerer cares about their feelings. Only a rude, uncaring person would make them feel bad by saying "you look fat in that dress". So answering "no" is a signal that they care about the asker enough to figure out what they're actually asking. The question has turned from one about the facts of the dress to one about the relationship between the speakers. It's better than asking "do you care about my feelings?" directly, because that question has far too obvious an answer; no one would ever answer it wrong, so it's not a credible signal of care.
One day, someone wants to know if a dress makes them look fat. They're going to an important gala and want to make their best impression, so they need to know the real answer. They know that they can't just ask "does this dress make me look fat?", since those words actually mean "do you care about my feelings?". So they include a request that the answerer answer honestly. The answerer does so, the asker figures out what to wear, and then has a great time at the gala.
Other people start doing this too whenever they want to know the real answer. Now there are two types of people: The ones who want validation and the ones who want the answer. But now the difference is evident; if one person asks "does this dress make me look fat?", everyone else knows that they're the first kind of person. This has all the same problems as explicitly asking "do you care about my feelings?". So they start adding on the "be honest" request as well, and the cycle repeats.
Every time someone wants an honest answer, they have to be more explicit than whatever method of asking is currently accepted in that society. You get people saying stuff like "Ok, I know that people always say this and it's not meant to be taken literally, but I promise I'm asking honestly. Please don't just give me the 'socially correct' answer, I swear I'm not going to be offended.", they get an honest answer, and then they get huffy about it. "Well I didn't want you to be that honest."
These loops of ever higher and higher abstraction erode the ability of people to usefully communicate. In our world this doesn't continue infinitely, since there are other forces pushing back, but they can still go surprisingly high. The result is a spectrum of ways to ask, where the more elaborate ways have an increased probability of honesty.
Different cultures end up stabilizing at different levels of this ladder. In American culture, it would be considered completely ridiculous to answer a question like "does this dress make me look fat" honestly, but many other questions can be taken at face value.
Iranian culture ended up at a much higher level on the ladder. It's expected there that very generous offers will be extended and politely refused several times in a row before any real communication happens. If your taxi driver in Iran says "you were a pleasure to have along today, fare is on the house" and you say "Oh wow, thank you. Bye!", prepare to have an angry taxi driver on your hands.
Impossible communications
I frequently find myself wanting to ask people for honest feedback about something I did. But many other people also ask for honest feedback, and would get upset if the answer is "too honest". The feedback-givers have no good way to know what's going to happen, so it's in their best interest to only give positive feedback and avoid the chance of offending the other person. Or even if both of us are ok with honesty and know that about each other, if we're in public they risk someone else overhearing the communication, not knowing that I'm ok with it, and perceiving them as rude.
This means that it is effectively impossible to communicate the statement "I want maximally honest and useful feedback" to someone else. Our society has disallowed communication of that piece of information.
A similar problem occurs when I notice something someone else could have done better. I don't want to force the feedback onto them, since that can easily lead to bad feeling. But if I ask "Hey, do you want some feedback about what just happened?", they can't say no without risking being seen as unreceptive or defensive. So I have to play convoluted social signaling games, where I incrementally edge closer and closer to the subject while giving them a chance to back out of the conversation in a way that allows them plausible deniability they aren't trying to avoid feedback.
This dynamic is everywhere.
If I ask someone for a favor, they might perceive it as rude to decline and then be resentful at me for putting them in a situation where they either have to be rude or agree to do a favor they don't want to do.
If I ask someone a potentially-awkward question and say "it's ok if you don't want to answer", they might be worried that my statement was a platitude and I actually would be offended if they don't respond. They feel forced to answer anyway.
If I offer to pay a friend to do me a favor, they might think that I don't mean it and feel that they have to either do the favor for free or decline to help me at all. Let's say I ask if I can stay at a friend's house. They like me, but it would also inconvenience them, and the inconvenience is slightly more than the amount of happiness they'd get from spending time with me. If I could offer to pay them $10 a night, that would tip the scales over to them preferring to have me over. But the aforementioned dynamic means that they'll have to refuse the 10$ out of "politeness", which means that they'll have to decline to let me stay over at all, since it's not worth it for them. Note how this has harmed both of us. I now have to pay more for a hotel, and they no longer make money by having a friend over. No one has benefitted from this!
One time I offered someone a $30 bet to demonstrate a point in a presentation. In order for the point to be demonstrated, it needed to be a real bet, with real money on the line.
In short, any topic that comes hand in hand with strong social expectations with have certain statements about it that are simply verboten. It's extremely difficult to accurately get ideas across in these domains.
Miscommunications
Humans naturally operate on many different levels of meaning, switching back and forth as the situation dictates. Often this is due to the previous described dynamics of needing to say something while having a fallback plan if it's received differently from what you intended. Sometimes it's also used for humor, as in a double entendre.
The vast majority of multi-level communication happens seamlessly. Context clues and shared prior information make it obvious which meaning is meant, and the recipient interprets it in the intended way.
But sometimes miscommunications happen. Someone says something that's supposed to mean one thing, but it gets interpreted differently. Or people conform to incorrectly-perceived social pressure and end up doing something they don't want to do. (And it's probably more often than you expect.) Consider how frequent it is for "obvious sarcasm" to be taken seriously. This can lead to friction between people who tend to operate on different communication levels.
For example, I attend a lot of judge conference presentations. If the presenter says something incorrect, I often speak up to correct them. My thought process is "I want everyone here to have accurate information". But sometimes this is interpreted as "Isaac is trying to undermine the speaker and make them look bad." People assume that I must have some sinister underlying motive driving my behavior and I couldn't possibly just care about preventing the spread of misinformation.
It can be extremely difficult to get people to understand that no, I actually meant what I said. Consider the following conversation I had with an acquaintance who's in charge of a group of people:
Me: "Do you consider it inappropriate for people in your group to do [thing]? If I see someone in your group doing [thing], should I contact you about it?"
Them: "[Other group] does not allow their members to do [thing]. Why do you ask?"
Me: "I want to know what to tell members of your group about your stance on [thing] if they ask me."
Them: "[Other group] has significant overlap with my group and their rules are very clear. Does that answer your question?"
Me: "Not really, no. I was already aware that [other group] doesn't allow [thing], and that I can talk to their leaders about it. My question is about your position, whether I should be talking to you about [thing] happening among members of your group, and whether you plan to encourage your members to not do [thing]."
Them: "Let me ask you a question: Do you think that members of my group doing [thing] is a significant problem? I'm not aware of it happening in large numbers. If you think it's a significant problem, I can talk to [other group]'s leaders and see if they want to take action about it."
Me: "I do think it's a significant problem, but that's not very relevant to my question. I was not requesting that you take action about [thing], I was asking what your current stance on it is so that I know how to answer questions about it from your group's members."
Them: "I appreciate your willingness to bring up potential problems regarding [thing]. I will discuss this with [other group] next week."
Me:
I was trying to find out exactly what I asked: What should I be telling people your policy is? But they seemed incapable of understanding that that really was what I wanted to know, and seemed to think I was trying to push them into changing their policy.
Them: "You tend to speak very literally, and myself and other people tend to read more into what you're saying than you meant for them to do."
Me: "I agree. I'm working on figuring out how to avoid that, but in the mean time I think it would lead to the fewest miscommunications if you tried to remember that I probably just mean what I say and aren't trying to communicate something wildly different via subtext."
Them: "Ok, I'll try to do that."
***A little later, while discussing the previous conversation about [thing]:
Them: "Here's why we don't think [thing] is very much of a problem and aren't taking action on it."
Me: "Thanks for the explanation! I think that's very reasonable. I just wanted to know what to tell people who asked me what to do when they see [thing] happening."
Them: ***Seems to think this meant I didn't understand why they aren't taking action about [thing] and proceeds to explain to me several more times why they don't think [thing] is a problem***
***A little later:
Them: "It took me several re-readings of our previous conversation to realize that you were speaking literally."
Them: ***Proceeds to talk about how I was asking them to take action on [thing].***
Me: "No, that's not what I was asking. I was asking for what your stance was on [thing]."
Them: "Well here's why some people might interpret your statements differently."
Me: "Yes I'm aware, we already went over that. You stated that I was trying to get you to take more action about [thing], and I was clarifying that the intention of my statements was not to communicate a request for action, but a request for information."
Them: "Got it."
***Later on***
Them: "So going back to our previous conversation where you were trying to get me to do more about [thing], I think it would be better if you had expressed that in this way..."
What I think is happening here is that this person's day job is to play politics and gain favor with other people and other groups, and they're very good at it. Those sorts of interpersonal games tend to include a lot of subtext, and as a result this acquaintance has adopted as their default that every statement has multiple buried layers of additional meaning, to the point where they were nearly incapable of taking things literally.
And remember that this was a situation where we were both aware of the communication disconnect and legitimately trying to overcome it. Things get so much worse when the situation is adversarial and both parties are unconsciously looking for ways to conveniently misunderstand the other one.
For example, during the Joe Rogan-Spotify controversy, several of my acquaintances made claims like "the progress of science demands that we censor people who disagree with the current scientific consensus". This made it pretty clear that they didn't know what the scientific method actually is, so being someone who likes science, I made a Facebook post explaining why this made no sense. Several people decided that this meant I was a Joe Rogan fan, since it was easier to come up with criticisms for that than for what I had actually said.
One of them helpfully provided an elegant example of how to use multiple levels of communication to deliberately mislead people while maintaining plausible deniability that they weren't trying to do that. They started messaging my acquaintances and saying "Isaac has been supporting arguments made by Joe Rogan". This statement is, literally, true. But it strongly implies something like "Isaac supports most arguments made by Joe Rogan" or "Isaac supports particularly objectionable arguments made by Joe Rogan". Listeners who aren't looking for deception will likely interpret it that way. But if the sender gets accused of trying to mislead people, they can say "Woah woah woah, my statement was true! Isaac supports people drinking enough water, and Joe Rogan has also advocated for drinking water." Or whatever.
(Sadly, it's not just Twitter.)
Restricting communication to only one level does not solve this problem. Multi-level communication is often used to communicate information to some listeners while hiding it from others, as in parody, innuendo, code words, dog whistles, euphemisms
My approach
I don't have a good solution to these issues. Completely ignoring other people's preferences is not a good solution.
I have a hard time recognizing subtext. For example, before publishing this article, I asked some people for feedback on it. Three of them said they would, then never did.
It's also difficult for me to recognize what tone I should adopt in what context. I never know what relationship I have with someone else; are we friends? Acquaintances? Enemies? Can I speak to them directly, or do I have to tiptoe around offending them? Should I be serious or joke around? None of this is obvious to me.
So I generally communicate more towards the literal end of the spectrum, and if I'm worried that something I'm going to say will be interpreted incorrectly, I say that up front and try to make the subtext (or lack of it) clear.
I avoid falsehoods and misrepresentation unless the alternative is significantly worse. I'm still willing to selectively omit information and imply things that I don't believe when it's necessary, but I look for reasonable alternatives first. A lot of social norms can in fact be satisfied without too much deception, just emphasis of some things over others.
And I try to clearly signal that I mean things literally most of the time.
I'm definitely not perfect at any of these. I often imply something or dodge a question without intending to do so, sometimes without even noticing afterwards. I get annoyed and let that color my phrasing. I find it very valuable when someone asks me "You said X. Does this also mean Y?" Often the answer is no, but sometimes it's yes, and this lets me know that I failed at being appropriately clear and explicit, and need to adjust.