This is a horrible thing to do to a Guesser. (I agree denotatively, but...)
It took me almost six months from meeting a particular Guess person to realise this: the times I offended them clustered according to whether I was a soldier in their war, not by my actual actions.[0]
Lots of things, maybe most things you can do in a conversation are horrible things to do to a Guesser. I'm well above average for social skills plus a few points above LW average IQ and even I find it hard to navigate conversations with a Guesser (I swear I have better social skills than that previous arrogant statement implies). The way I have found to not constantly insult and offend them is to take a lot of time to learn their particular 'dialect' of Guess.
I didn't grow up in a Guess culture, so at my first exposure to it I was already a mind that could think for itself - and my thought was "Guess culture is manipulative." It stacks up complicated laws, some of which are enforced ridiculously strictly[1] and others that are loosely enforced, if at all[2], so a skilled Guesser has both a minefield of rules, and an arsenal of selectively enforced rules, to use in conversation.
This is scary. If I walk into a conversation with a Guesser and I have something at stake, I am likely to lose that stake. Dealing with them feels like dealing with a negative utility monster; I must sacrifice too much to avoid offending.
(Please don't vote this post up because it bashes the hateful Guess enemy; evaluate it on its merits.)
0: I could use ableist slurs (insane; crazy) freely to deride people, institutions, papers etc that argued for no gendered pay gap, for biological difference between race, etc. But it was a serious transgression to use the same slurs to describe people, institutions, or papers that argued for parapsychology, telepathy, etc. Once I noticed this, I tested it experimentally - even when you know you're doing it for science, it hurts to offend a Guesser.
1: "Giving a negative response when someone asks for evaluations on their appearance / idea / whatever" is banned. (The only way you can provide that information is to guess at their personal evaluation, and then give the least warm approval you think has a plausible interpretation that agrees with their actual personal evaluation, which will be revealed only after you've made your social move. Yech.)
2: Gossip is frowned on. You can gossip all you like until you say something they don't like hearing, at which point you've offended them by gossiping.
What's your policy for interacting with Patrick? Do you get along? I have some of the same problems you describe about walking on eggshells around Guessers.
Followup to: Ask and Guess
Ask culture: "I'll be in town this weekend for a business trip. Is it cool if I crash at your place?" Response: “Yes“ or “no”.
Guess culture: "Hey, great news! I'll be in town this weekend for a business trip!" Response: Infer that they might be telling you this because they want something from you, conclude that they might want a place to stay, and offer your hospitality only if you want to. Otherwise, pretend you didn’t infer that.
The two basic rules of Ask Culture: 1) Ask when you want something. 2) Interpret things as requests and feel free to say "no".
The two basic rules of Guess Culture: 1) Ask for things if, and *only* if, you're confident the person will say "yes". 2) Interpret requests as expectations of "yes", and, when possible, avoid saying "no".
Both approaches come with costs and benefits. In the end, I feel pretty strongly that Ask is superior.
But these are not the only two possibilities!
"I'll be in town this weekend for a business trip. I would like to stay at your place, since it would save me the cost of a hotel, plus I would enjoy seeing you and expect we’d have some fun. I'm looking for other options, though, and would rather stay elsewhere than inconvenience you." Response: “I think I need some space this weekend. But I’d love to get a beer or something while you’re in town!” or “You should totally stay with me. I’m looking forward to it.”
There is a third alternative, and I think it's probably what rationalist communities ought to strive for. I call it "Tell Culture".
The two basic rules of Tell Culture: 1) Tell the other person what's going on in your own mind whenever you suspect you'd both benefit from them knowing. (Do NOT assume others will accurately model your mind without your help, or that it will even occur to them to ask you questions to eliminate their ignorance.) 2) Interpret things people tell you as attempts to create common knowledge for shared benefit, rather than as requests or as presumptions of compliance.
Suppose you’re in a conversation that you’re finding aversive, and you can’t figure out why. Your goal is to procure a rain check.
Here are more examples from my own life:
The burden of honesty is even greater in Tell culture than in Ask culture. To a Guess culture person, I imagine much of the above sounds passive aggressive or manipulative, much worse than the rude bluntness of mere Ask. It’s because Guess people aren’t expecting relentless truth-telling, which is exactly what’s necessary here.
If you’re occasionally dishonest and tell people you want things you don't actually care about--like their comfort or convenience--they’ll learn not to trust you, and the inherent freedom of the system will be lost. They’ll learn that you only pretend to care about them to take advantage of their reciprocity instincts, when in fact you’ll count them as having defected if they respond by stating a preference for protecting their own interests.
Tell culture is cooperation with open source codes.
This kind of trust does not develop overnight. Here is the most useful Tell tactic I know of for developing that trust with a native Ask or Guess. It’s saved me sooooo much time and trouble, and I wish I’d thought of it earlier.
"I'm not asking because I expect you to say ‘yes’. I'm asking because I'm having trouble imagining the inside of your head, and I want to understand better. You are completely free to say ‘no’, or to tell me what you’re thinking right now, and I promise it will be fine." It is amazing how often people quickly stop looking shifty and say 'no' after this, or better yet begin to discuss further details.