Who asks and who guesses has a lot to do with social roles.
If I'm out dancing Salsa it's usually men doing a lot more asking and on the other hand woman often being more indirect about wanting to dance. That doesn't mean that woman never ask a man to dance but usually it's the role of the man to ask.
It took me quite a while to get to the point where rejection in those situations doesn't trigger much in me anymore most of the time and there are still situations where it does. Some cases where I don't feel any pain then when I meet the girl another day and we dance I'm more held back and the intimacy between us is less even if the girl would want a bit more.
It quite easy to say: "You are completely free to say ‘no’". On the other hand it's hard to not feel rejected. When someone I consider unconfident says: "You are completely free to say ‘no’", I might translate that into that they might hurt emotionally from getting a "no" but won't actively hold it against me. Even if the don't want to hold it against me, they might still put up emotional shields that prevent further rejection from hurting.
I think the framework of Nonviolent-Communication works quite well. You are open with what you are feeling and don't judge. If the emotions are out in the open it's a lot easier to deal with them.
People's feelings do sometimes get hurt when you say "no". And people's feelings get hurt when you're honest with them sometimes. My thesis is that it's easier, as a community, to recover from hurt feelings than from ignorance and deceptions.
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.