The whole thing hinges on how much you trust people when they assure you you can say potentially upsetting thing X to them. Generally, not very much. I would never trust a sticker or declaration to the extent that I wouldn't model someone's response, it's just an update on that model.

It was emphasised that people didn't have to answer any question, but the empathy should have been equally pushed.

On this occasion, askers were very hesitant to ask questions they thought would be too personal, but those being asked invariably responded without any hesitation or unease. Discovering that you could ask personal questions you were curious about with only the positive consequences of closeness and openness was a win.

But this does all include a good deal of judgment. Not an exercise for a group not high in empathy or generally unconcerned about others' responses, nor for those who are easily pressured.