Rick Saenz has a post in which he links to a post on the difference between Ask Culture and Guess Culture. The fellow he quotes says,

This is a classic case of Ask Culture meets Guess Culture.
In some families, you grow up with the expectation that it’s OK to ask for anything at all, but you gotta realize you might get no for an answer. This is Ask Culture.

In Guess Culture, you avoid putting a request into words unless you’re pretty sure the answer will be yes. Guess Culture depends on a tight net of shared expectations. A key skill is putting out delicate feelers. If you do this with enough subtlety, you won’t even have to make the request directly; you’ll get an offer. Even then, the offer may be genuine or pro forma; it takes yet more skill and delicacy to discern whether you should accept.

…

I’m a Guess too. Let me tell you, it’s great for, say, reading nuanced and subtle novels; not so great for, say, dating and getting raises.

This is a distinction I’d not run into before, and it explains why I sometimes miss the subtleties in nuanced and subtle novels…because I’m an Asker all the way.

I call it the Pony Principle: If you really want a pony, you should ask your parents for a pony, even if you’re sure they will say no. You almost certainly won’t get a pony…but who knows? Your parents’ notion of what’s reasonable might be different than you think. But if you don’t ask for the pony, you certainly aren’t going to get it. So ask for what you really want…but be prepared to be told no, and don’t make a fuss if you are.

True story. Many years ago, Jane and I were on a road trip with our two very little boys, and we were stopping for the night in Las Vegas (which was still in its “Let’s pretend we’re family-friendly” phase). We arrived rather earlier than we’d planned, and even though it was nowhere near check-in time we asked politely if we could check in anyway. The lady at the desk told us that our room hadn’t been cleaned yet, but we could check back in an hour. We went at got lunch, and came back, and we waited in line and explained, and the second lady we talked to told us that she was sorry, but it still wasn’t ready.

And we said, “Thank you, we’ll check back again later; we know it isn’t really check-in time yet.”

And an hour later, the first lady saw us coming, waved us over to an empty spot, and told us that the hotel was giving us a free upgrade to a much nicer room, so that we could get settled with our little boys. I can only assume that it was because we were pleasant and polite and didn’t make a fuss.

So ask for what you want; be willing to take no for an answer; be nice about it; and if you know you’re asking for something unreasonable, make it clear going in that you’re willing to take no for an answer.

If you’re dealing with a Guesser, though, you’re on your own. I’d be no help at all.