Given the importance of communication style in interpersonal relationships, I am looking to create an OkCupid question to determine if someone is an asker/teller or guesser. I'm having difficulty creating an unbiased question. Any way I've written the question makes ask/tell seem obviously better, e.g., here are two possibilities:

1. When you want someone to do something for you, do you prefer to ask them directly or do you prefer to mention something related and expect that they infer what you want?

2. Should your partner "just know" what you want without you ever saying so explicitly?

That perception might just be my own bias. Quite a few people I know would probably answer #2 as yes.

Unfortunately, this question probably won't be answered very often, so it's also useful to look for a proxy. Vaniver suggested a question about gifts when I mentioned this at a meetup, and I believe he meant the question "How often should your significant other buy you gifts, jewelry, or other things more expensive than, say, dinner, cards, or flowers?" This question is a reasonable proxy because many guessers I know seem to expect people to "just know" what sort of gifts are appropriate for them. Unfortunately, many guessers might not care that someone buys things for them with any regularity.

Another possibility is "Imagine that a friend asks you to read a short story they wrote. Unfortunately, you find it to be very boring. Which is closest to how you might respond when they ask you what you think of it?" I think that indirectly gets to the core of the ask vs. guess issue. Saying negative things is considered inappropriate to most guessers. Any other potential proxy questions?