Which personal, deep, or inappropriate questions would you find interesting to be asked on a first date?

8 comments

1. >inappropriate

   By definition, none.

2. [removed]

3. “would you ever try human flesh? Like not in a survival situation, but just to try it?”

4. What is your weirdest ick/fear?

5. “what about you feels hardest to love?” i was asked this a new friend and it just opened up such an open space i’ve never felt with a new friend.

6. “Do you ever think about if your younger self would be proud of the person you are now?”

   It was more toward himself because we were both fresh out of college 20-somethings, but I still think about it a lot.

7. Have you ever had an abortion?

   True story, I was asked that on a first date.

8. I really love answering all kinds of questions, so to me, anything that is not straight up creepy or insulting is welcome, even deeply personal things. Questions like, what’s your biggest fear, regret, or trauma – all of them interesting to me and I would not have tough time asnwering.
   But in reverse, I would never ask those myself on first date, as I’m really mindful of how other person might feel and don’t want to make things awkward.