I recently stayed at a B&B owned by a nice elderly couple. Very, very nice. The moment I stepped in the door, they asked how my flight was, where I was from, what I did, how I'd enjoyed my three minutes of visiting their city so far, what kind of food I liked, what my favorite color was, et cetera. I played along - no point in offending people - but I warned that my friend, who would be arriving a little later, was much more introverted, and would appreciate being efficiently directed to her room without the welcome committee.
A little later, my friend arrived. From my room, I could hear them start welcoming her, ask her how her flight had been, start trying to get to know her - until I ran out and rescued her, for which she reports gratitude. For the rest of our stay, they continued to talk both of our ears off, with my friend growing increasingly annoyed and uncomfortable.
We spent the trip back dissecting what had gone wrong. Neither of us believed the proprietors didn't care about her feelings: they were so very, very nice. They couldn't have forgotten my warning; my friend arrived less than an hour after I did. We concluded that they were just inexplicably bad at some sort of mental gear-shifting.
The worst part was, I knew this would happen. When I told them to please respect my friend's introversion, there was a voice in my head quietly adding "...even though you obviously won't and I have no idea why I am even making this request".
I tried to trace my certainty back, and found myself remembering a telephone call with my grandmother. She asked me what I was getting my girlfriend for the holidays. I said my girlfriend had told me unprompted that she found getting holiday presents weird and awkward and would prefer I not give her anything. I'd challenged her on this - what if I try really hard to pick something you like? - what if I leave it on your doorstep and you're under no obligation to demonstrate any emotion to me? - satisfied myself that this wasn't some complicated attempt at emotional manipulation, and agreed not to get her a holiday present. My grandmother said I was wrong and should get her a present anyway. I tried to get her to explain her reasoning. It wasn't that she thought my girlfriend was lying, or trying to manipulate me, or that she had some special idea for an amazing present that overcame her objections. It was just "Everyone loves presents!". Nothing that I said could scale the wall of sublime certainty she had erected around this statement. Everyone loves presents, and so my girlfriend's request that I not give her a present was inaccurate.
(I mock, but one of my girlfriend's friends gave her a present and she loved it. It's not that my grandmother was necessarily wrong, just that she was following a very different cognitive algorithm than I usually do)
And I could have predicted this one too! Growing up with my family, it was weird how often I would express a preference, and they would - compassionately, and as far as I know without a trace of malice - say "No it isn't," and keep doing the opposite.
When other people's behavior baffles me, I try to think of an example where I make the same mistake; this usually shows up pretty fast, and I get appropriately humbled. But I'm having trouble. There are things that are close - part of me will always refuse to believe that people enjoy living in New York City, and whenever I talk to friends in New York I have to resist the urge to ask them if they're okay, or whether I can help them move. But it stays at the level of intellectual curiosity; I would never refuse to drive an NYC friend to the airport because I don't believe them when they say they want to go back home.
I had a patient who dated an extremely unstable and abusive partner. Every time he described what was going on, I asked him whether he was sure he wanted to stay in the relationship. He always said yes. I did a lot of therapy with him that might be uncharitably described as "help him understand himself well enough to realize that he actually hates her and wants to leave the relationship after all". He did not. He kept insisting in every therapy session that he was quite happy with her and this was the person he wanted to spend the rest of his life with. I don't feel too bad for finding this suspicious. If I somehow had the power to make him break up with her, would I use it? Maybe. Still, "guy is happy in his abusive relationship" feels, just, more inherently questionable than "friend is an introvert" or "girlfriend does not like presents".
One possible confounder: when I see this, it's almost always older people. Very nice older people. The example par excellence is the housekeeper from Father Ted:
I'm neither especially old nor especially nice. But I know that the Old Days had more pressure for social conformity. If you were a mean person, you enforced social conformity by punishing deviants. But if you were a very nice person, maybe you didn't punish. Maybe you just denied that deviance was possible. Don't make a scene about it, and they won't want to make a scene, so they'll back down quietly. Problem solved!
Or maybe it's more about cognitive flexibility. You start with a model - people are like this. A Jungian would call it an archetype, a cognitivist would call it a schema, a Kleinian would call it an object, a Bayesian would call it a prior. Then when you get extra evidence, you update away from your prior. So you start off thinking the average person likes presents. Then someone says they don't. You may not want to update an infinite amount from this one comment; maybe you misunderstood them, maybe they're just having a bad day, maybe they're more normal than they think but don't understand themselves very well (the local four-year-old recently announced she had no sense of taste, something we're pretty sure is some kind of weird game she's playing with herself and not true at all). So you have to make some particular finite update. If you're bad at calibrating updates, maybe getting told "I don't want a present" isn't enough to convince you not to give someone a present.
Or, put another way, I think it's hard for conscious people thinking rationally to get this one wrong. But our emotional reasoning machinery gets stuff dumber than this wrong all the time. My favorite is "Hey, maybe this person who constantly does stuff with me and supports me and stands by me through thick and thin and says they're my friend is actually my friend...nah, they're probably just doing it out of social obligation and secretly they hate me." Or "Maybe this woman is rejecting me and telling me to go away and saying she isn't attracted to me because she actually isn't attracted to me...nah, must just be one of those games women play." Or "Maybe this woman is flirting with me and saying she likes me and asking me out on a date because she actually wants to date me...nah, that would be crazy, must be another one of those games." Honestly it is a miracle our species has survived this long.
Maybe I'm biased / placebo-ed / just seeing things, but my impression is that the same people who are good at taking ideas seriously are also good at respecting preferences. If you're the sort of person who, upon hearing a good argument for cryonics, will start looking into how to freeze disembodied heads, you're probably good at making large updates away from common-sensical priors really quickly. I find that if I tell one of these people my weird preference, they'll take it into account quickly and without protest. Maybe in the transhuman future, when only the cryonauts’ disembodied heads are left, I'll finally be able to get nice people at B&Bs to stop talking.