There's a concept (inspired by a Metafilter blog post) of ask culture vs. guess culture. In "ask culture," it's socially acceptable to ask for a favor -- staying over at a friend's house, requesting a raise or a letter of recommendation -- and equally acceptable to refuse a favor. Asking is literally just inquiring if the request will be granted, and it's never wrong to ask, provided you know you might be refused. In "guess culture," however, you're expected to guess if your request is appropriate, and you are rude if you accidentally make a request that's judged excessive or inappropriate. You can develop a reputation as greedy or thoughtless if you make inappropriate requests.
When an asker and a guesser collide, the results are awful. I've seen it in marriages, for example.
Husband: "Could you iron my shirt? I have a meeting today."
Wife: "Can't you see I'm packing lunches and I'm not even dressed yet? You're so insensitive!"
Husband: "But I just asked. You could have just said no if you were too busy -- you don't have to yell at me!"
Wife: "But you should pay enough attention to me to know when you shouldn't ask!"
It's not clear how how the asking vs. guessing divide works. Some individual people are more comfortable asking than guessing, and vice versa. It's also possible that some families, and some cultures, are more "ask-based" than "guess-based." (Apparently East Asia is more "guess-based" than the US.) It also varies from situation to situation: "Will you marry me?" is a question you should only ask if you know the answer is yes, but "Would you like to get coffee with me?" is the kind of question you should ask freely and not worry too much about rejection.
There's a lot of scope for rationality in deciding when to ask and when to guess. I'm a guesser, myself. But that means I often pass up the opportunity to get what I want, because I'm afraid of being judged as "greedy" if I make an inappropriate request. If you're a systematic "asker" or a systematic "guesser," then you're systematically biased, liable to guess when you should ask and vice versa.
In my experience, there are a few situations in which you should experiment with asking even if you're a guesser: in a situation where failure/rejection is so common as to not be shameful (i.e. dating), in a situation where it's someone's job to handle requests, and requests are common (e.g. applying for jobs or awards, academic administration), in a situation where granting or refusing a request is ridiculously easy (most internet communication.) Most of the time when I've tried this out I've gotten my requests granted. I'm still much more afraid of being judged as greedy than I am of not getting what I want, so I'll probably always stay on the "guessing" end of the spectrum, but I'd like to get more flexible about it, and more willing to ask when I'm in situations that call for it.
Anyone else have a systematic bias, one way or another? Anybody trying to overcome it?
(relevant: The Daily Ask, a website full of examples of ways you can make requests. Some of these shock me -- I wouldn't believe it's acceptable to bargain over store prices like that. But, then again, I'm running on corrupted hardware and I wouldn't know what works and what doesn't until I make the experiment.)
I was raised in a strong Guess culture, then went to a tech university where Askers predominated, and it took me some years to come to terms with the fact that these are simply incompatible conversational styles and the most effective thing for me to do is understand which style my interlocutor is expecting and use that.
This, amusingly, often leads me to ask people whether they are using Ask rules or Guess rules. Except, of course, in situations where I intuit that asking them would be inappropriate, and I have to guess instead.
Bringing college friends home for dinner was the most wearing version of this. On one occasion I had to explicitly explain to a friend that, for her purposes, it was best to assume that the last piece of chicken was simply unavailable to be eaten, ever, by anyone. (There actually was a method for getting it, but it was an Advanced Guess Culture technique, not readily taught in one session.)
Incidentally, my own experience is that Ask and Guess are sometimes misleading labels for the styles they refer to (though they are conventional).
For example, "Ask" culture is often OK with "So, I'm assuming here that A, B, and C are true; based on that yadda yadda" with the implicit expectation is that someone will correct me if I'm wrong. In "Guess" culture this sort of thing carries the equally implicit expectation that nobody will correct me. Here both groups are guessing, but they guess differently.
"Guess" culture also has an implicit expectation in some cases that you do ask, but that an honest answer is not actually permitted... the answer is constrained by the social rules. For example, growing up if a guest says "Well, we should get going." the host is obligated to reply "Oh, but we're having such a good time!" and none of that actually lets you know whether the guest is still welcome or not (or, indeed, whether the guest has any desire to stay or go). (On one occasion, when highly motivated to have a departing guest take leftovers home with her if and only if she actually wanted leftovers, but not knowing her default rules, I ended up saying "So, among your tribe, how many times do I have to repeat an offer to have it count as a genuine offer?")
And "Guess" culture has all kinds of rules for how you communicate to someone exactly what it is you want them to do without being asked.