* In the clash of another cultural concept: I prefer to refer to people by name when I'm talking about things they said. But I'm not doing that here because I don't know if the individuals involved want to be quoted by name or not. I also don't have convenient Twitter or LJ handles to refer to, which makes credit more complicated.
There are some things I've thought about this concept since I first heard of it. Like most dichotomies, it oversimplifies. Most people may lean one way or the other, but they are not going to be pure "Ask" or pure "Hint" about all things. Also, people vary in what they are Ask vs Hint about. You might be Ask-culture when it comes to visiting friends: "Would you like me to come over so we can play games?" but Hint-culture about birthday gifts: "I love Scharffenberger chocolate!" Or you might be the reverse: "It's always so much fun when we play games at your place!" and "Here's my Amazon wishlist!" You might feel it's unreasonable to ask directly for someone to email but normal to ask them to call, or the exact opposite, or that both are appropriate, or that neither are. People's inner rules about "this is too much to ask so I can only hint about wanting it" vary a lot.
My family is probably more "Ask" than "Hint": we are good with words and somewhat oblivious in general. But there are lots of things that I won't ask for. For example, when I realized that I needed a car, one of my friends pointed out that shipping a privately-bought used car halfway across the country was cheaper than the premium for buying a used car from a dealership. My parents have two cars and they basically don't use the second one: my mother almost never leaves the house without my father. It occurred to me that I could ask to buy their second car, which is a nice car in excellent condition because it's rarely driven. But I didn't, in part because asking for their car -- even asking to BUY their car at full market value -- felt like an unreasonable request. I told them I was planning to get a car and if they had offered to sell theirs, I'd've taken it. But they didn't, and I didn't ask, and that's fine.
One of the reasons that I am aware of how much I am not "Ask" culture is that I know someone who is. This is the person who inspired Wisteria, my character who is congenitally unable to take hints. And once I start thinking about all the areas where I expect hints or try to interpret them, I realize how much I rely upon them. For example, I was working with someone on a project where I hadn't heard from them recently, so I checked to make sure I'd responded to their last request and I had. But I hadn't gotten a reply, so I wanted to make sure now that they'd seen my email. We were still well-within the agreed-upon time frame so it wasn't a problem yes, but if spam filter or something had claimed my email, it would become one. I reached out on a different channel and said: "Oh hey, just wanted to make sure you got my email from [X Date]. No worries if you're busy and haven't gotten to the next step in the project yet, just making sure my email got through. :)" I included the second sentence specifically because I would react to the first sentence as "I expected to hear from you by now and I am deeply disappointed that you haven't finished the next step yet, what is your problem?" So even though the first sentence is at most a Hint, I still want to make sure that it has the right Hint-culture connotation of "I really do just want to make sure you got the email and are not waiting on me. I am not resentful or rebuking either your work or communication rate."
"Ask" and "Hint" cultures both encourage different failure modes. The failure mode of "Hint" is "passive-aggressive". Properly-done, Hint culture is designed to save face by giving both parties a graceful way out of a request. If you are eating chocolate, and I say "I love chocolate", and you say "Isn't it great?" and finish your chocolate without offering me any, then I can think "well, I didn't ask so you probably didn't realize I wanted some" and you can think "she didn't ask me for my chocolate so it's okay that I didn't share." If I simmer with resentment that you didn't offer to share your food when I Hint that I want to try it, or if you simmer with resentment that I Hinted that I want you to share, then we are Doing Hint Wrong.
The failure mode of "Ask" is "abrasive". This is the person who is "just being honest". The person who responds to "should I wear my blue dress or the red dress?" with "Those are both ugly". "Ask" culture is not a license to say anything because it's just words, and it's not a license to keep making the same request after being refused because "it doesn't hurt to ask." There is a point in Further Arrangements where Wisteria asks Justin to explain his reasoning, and Justin's reply amounts to "...because I'm an idiot." Wisteria doesn't accept this response: "My inability to follow your reasoning is my failure, not yours." This is an important facet of Wisteria for me: she can't properly participate in or understand Hint culture, and it frustrates her a lot -- but she doesn't believe Hint culture is innately inferior. It works for other people. It just doesn't work for her.
I have a lot of sympathy for people across the spectrum. I tend to assume the best about people, so if someone makes a request that I find too blunt, I think "they probably don't realize how it sounded and are not being pushy." If someone misses my hints, I assume they didn't notice them, because I know how often I miss hints. If I notice something that look like a hint to me, but I don't want to accede to the implicit request because I think it's unreasonable, I assume the hint was unintentional. Yo, guys, I am so bad at humaning. I'm gonna assume this is just as hard for the rest of you.