Questions I wish were socially acceptable to ask on a first date

The older I get, the more I notice two things about myself:

1. I really love getting to know people. I want to know all of what makes them different from me. How has the sum of their experiences thus far shaped who they are? What does that tell me about humans in general? What do I have to learn from them? Conversations about these deeper things GIVE ME LIFE maybe a little more than most. You’re probably a good friend of mine if we’ve crossed paths and you, too, like contemplating the weirdness of humanity. And,

2. More and more I feel the pressure of our time being such a precious commodity. Something about seeing my grandparents get older makes me want to just cut to the chase with every person I meet. It seems a tragedy to me when a coworker changes jobs and I only got to know them on a very surface level (I’ve always been sentimental, and I guess aging only exacerbates that.)

So that means the poor saps who go on dates with me (thanks bumble) are under a lot of pressure. If it takes too long for us to get to conversations that would lead to the below topics, I get bored and want to move on. I wish I could ask them all of the below the first time we meet, but I also need to understand that not everyone is as open of a book as I am. And that’s okay. I try to remember that personal conversations are earned, not just freely given away. So, with that wordy intro, here are the questions I wish I could ask first dates (and really, everyone I care about). These are likely only the tip of my question iceberg:

  • What do you think God, or life, or whatever is teaching you lately?
  • What’s one regret you have from this week? This month? This year?
  • What’s your favorite song and why?
  • Why is your best friend your best friend?
  • What’s your relationship with each of your parents like? Do you think that shapes much of who you are in your day-to-day?
  • What do you want your life to look like in 10 years? Has that vision changed much in the last 5?
  • What are you most looking forward to?
  • What did you learn from your last relationship?
  • What’s your favorite book?
  • What have you learned about marriage by watching your parents’ (or lack thereof)?
  • What area of your life do you need to give yourself a break on?
  • What area of your life do you need to be harder on yourself on?
  • Do you ever feel guilty about the number of kids you want, considering our generation’s obligation to a little more social responsibility than the previous one?
  • How do you know when you’re in love/what does love mean to you?
  • What do you wish that we as a society would just chill out about?
  • How would you describe yourself using five “I’m the kind of person who ____________” statements?
  • What do you, specifically you, need in a partner? (Can’t say cookie-cutter things like loyalty, honesty, etc. or the date is over.)
  • What’s your philosophy around personal finances?
  • What is saving your life right now?
  • Do you think people are mostly good?
  • How much of your happiness can money buy?
  • What are you most scared of?
  • What’s one thing you wish you could change about yourself?
  • What are some things you like about yourself?

Author: Alex Ethridge

Hi, I'm glad you found me.

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