This one’s similar to the fourth one (What do you usually do when someone is annoying you?).
He wants to find out In time about your definition of a bad date so that he doesn’t make the same mistakes like guys before him.
Evidently, he likes you a lot, and he’s ready to do anything to prevent fucking things up with you.
And that’s the main reason why he would ever decide to ask you these weird questions in the first place. Witty, I know.