I think one comment the original poster (mama_hogswatch) made says something about each culture quite well:
The "Guess" culture expects other people to protect their boundaries.
The "Ask" culture protects their own.
I grew up in a "Guess" culture, but am actively changing to an "Ask" culture. There are still times when I hesitate to ask, but thanks to my last visit to St. Louis those are very rare now.
What about you?
Which culture did you grow up in?
Which culture are you now?
I was going to make this part of the poll, but decided to leave it off in favor of putting it in the comments. Once you've submitted your answers come back and tell me in your own words any further thoughts you have about the "Ask" and "Guess" cultures. (Specifically, if you're of the "Guess" culture, why?)