RANDOM ADVICE FROM DATING COACH:
My favorite way to learn about a person is through storytelling.
I share a personal story and get their opinion on the situation. It makes exploring boundaries a lot easier bc their guard is down and they aren't trying to impress you or think "hmm what would I really do". It's a trick way to reach the subconscious instead of the ego.
If you're uncomfortable with sharing your own personal life (you all know I definitely am, haha) I recommend using a celebrity situation. Bring up what's happening in politics, religion, all of that stuff.
Everyone says to avoid those conversations on dates.
I say jump in.
The faster you know someone's true colors, the less waste of life takes place.