As best I can tell, "people who sometimes ask questions they might not want to hear the answer to" are a large majority of the population. "Does this dress make me look fat" is a cliche put-you-on-the-spot question for a reason.

You're misunderstanding the message.

"Does this dress make me look fat?" is not really a question. It's a request for a compliment.

If I may engage in gender generalization for a moment, men usually understand words literally. This annoys women to no end as they often prefer to communicate on the implication level and the actual words uttered don't matter much.