[Jverse]

I understand that you want to stand out and go beyond platitudes and canned answers. But for me, I always get a bit uncomfortable with these sorts of questions.

I've been on dates where I've gotten a barrage of questions like these. What makes me feel like backing off is that they seemingly come out of the blue and appear as canned interview questions. I also get the feeling that I'm getting judged on my answer. That some answers are more "right" than others, for example the article's question about material gifts versus experiences. Will I tick the box as materialistic if I mention that my best gift was an object?

[jhbadger]

Yeah, I can see these as "off-the-wall" questions in a job interview but if somebody started asking me these at a party or something I would be seriously weirded out and would quickly find an excuse to go talk to someone else.

[malux85]

Wow I’m really surprised by answers in this thread - I just read the article and questioned myself on all of these, and thoroughly enjoyed thinking about them, when they finished I thought to myself “I wish I had someone to talk to right now and ask these questions with”

I guess everyone is different, I’m just offering a counterpoint, I thought these questions were thought provoking and interesting and don’t find them intrusive or anything.

[Zambyte]

These questions aren't meant to be a substitute for conversation, they are meant to be something to give it direction when there is none. If they were simply barraging you with questions, either they were bad at listening and replying to what you said, you were bad at replying in a way that they could reply to (asking your own, related questions maybe?), or both.