Questions to Ask a B on a First Date

AKA I’mma Be a Single Harpy Forever

After being Surprise Dumped rather unceremoniously earlier this year by a person who had until that point pursued me hard & proffered, unsolicited, dreams upon dreams of our future together, I felt, well, pretty much like a greasy fast food bag, with a half-eaten chicken sandwich inside that the consumer had discovered to contain a lump of indistinguishable material, thus prompting them to discard the rest of the meal, squish the bag, & toss it out of their car window in the general direction of a trash can, with little regard as to where it landed. Run-on sentence aside, I felt & still feel like shit – replaceable, disposable, unnecessary, unwanted shit.

I’ve been exploring some of my patterns in relationships since then. Why do I sometimes date sociopathic liars, for one. Why do I often vacillate between dating people with whom there is clearly no future (they are not that into or open with me/I am not that open with them/we call it casual at the beginning & all throughout) OR dating people who swear up and down I am their everything until I inevitably find out they were lying to me all along about loving me/wanting a future with me/the fact that they are hiding significant relationships or keeping other fucked up secrets from me?* Run-on sentence number 2 aside, this post will answer exactly zero of these questions.

broken heart

What it will do, instead, is show you how I’m safeguarding against ever dating anyone, whether charming sociopath or emotionally absent flesh-pillow, ever again.

I’ve compiled a list of First Date Questions to ask anyone with whom I might ever again find myself picking at tapas, complaining that the house white wine isn’t as dry as we had hoped it would be, & trying to hide our individual brands of crazy**. I figure, if I ask them these things, they will know to leave immediately & stay far, far away, ensuring that my stupid fragile heart will never be put through the BabyILoveYouWaitJustKidding blender ever again.

If somehow, the person manages to answer these questions or at least be amused by how my poor li’l brain is trying to take care of my poor li’l heart, then maybe we can go on a second date. Definitely not holding my breath for this latter scenario, though.

Without further ado:

First Date Questions

1. What is your relationship to trauma?

2. What are your preferred healing modalities?

3. Tell me about a time that you hurt someone. What did you learn? How have you done things differently since then?

4. Do you believe in god?

5. What do you think about climate change?

6. What are some solutions to our current social ills?

7. What kind of art do you like to make?

8. What is your biggest weakness?

9. What is your biggest fear?

10. What do you do when you receive difficult feedback?

11. What would your last ex tell me about you?

12. What would your first ex tell me about you?

13. What would your best friend tell me about you?

14. Name 2 or 3 friends who tell you when you’re fucking up. What about their approach lets you hear them?

15. Name a challenge in your family of origin & how it has affected you. What is your relationship like to your family now?

16. How do you prefer to handle conflict?

17. Tell me about a time you had to tell someone they did something to hurt you.

18. What are the core things you think people need to agree on to be able to have a healthy & sustainable romantic relationship?

19. Tell me how you feel about hierarchy.

20. What do you do when you notice your actions are out of alignment with who and how you want to be?

21. What is your greatest strength?

22. What’s one thing you want to be great at but aren’t there yet? How are you practicing getting better at it?

23. What is one way you incorporate joy into your every day?

24. Do you like children?

25. How do you feel about animals/pets?

*Shout out to the few people with whom I have had amazing, loving relationships that simply didn’t work out & eventually transformed. You know you don’t fall into either of these categories & you know who you are.

**I identify as mentally ill. I identify as crazy. I use this word because I am crazy. It is ableist behavior to use this word to mean something it does not (ie. “That song is crazy!”)

23 thoughts on “Questions to Ask a B on a First Date

  1. Fantastic !
    By creating those questions and conditioning your subconscious to recognize the affirmative evidence of the positive embodiment of those qualities you seek you are aligning yourself with what you really want. No need to close yourself off to the flow of connection as you are manifesting success as you reflect on your personal victories in life and your positive attributes. Win big !

  2. If I ever go on a date (you know, in my next life) I’ll bring this list of questions with me. Great writing. I appreciate a well written sentence that masquerades as a paragraph. Keep it up.

    1. Awesome, thanks for your support, rollinglikeaball! It’s funny because a lot of people have taken this very seriously & have said things like “This is way too invasive to ask on a first date!” – they must have missed the cheekiness. Personally, I think keeping the list to reference is a good move. 🙂

  3. This is a really great list, for potential partners/friends/even just introspection. Also, I appreciated your note**, and your appropriate use of “stupid”. It felt somehow clever haha

  4. thank you for this. this helped me reflect on my current relationship and allowed for some proper and much needed self criticism. as someone else who also I dentifies as mentally ill and is generally quite secretive (defence mechanism primarily), even to myself, answering these questions to myself gave me some unexpected answers. perhaps not the intended purpose but still a good way to check oneself. much, much respect – I will be certainly be sharing.

    1. Your defense mechanisms are doing a great job at helping take care of you, so first & foremost I honor that! & I’m glad you pushed yourself a little bit – sounds like you got some good insight. Thanks for your support!

  5. This is hilarious and brilliant! I relate a lot with your experiences and I appreciate your witty expression of such a painful situation. It is incredibly hard to be a wise woman in a sea full of traumatized narcissists. Though I am surrounded with beautiful people in my life, the search for two connection and authentic conversion is still hard to come by. I love these questions. I am provoked to answer them for myself and explore my own insert landscape. Though I’m sure at some level I have already, it does help to reflect our core values. And ultimately to find out who people are beyond the shallow confines of our mediocre dating rituals. Blessings love~ feel free to follow my blog wildhoneywisdom.com. I’d love to connect as writers and as women.

    1. Thanks so much for your note! It’s life’s biggest mystery, finding that big amazing (romantic) love, I think. One note: I would like to lovingly challenge your assumption that I identify as a woman. So many things we can’t know about people just from appearances! Thanks for considering that & great to connect with you!

  6. I’ve been saving this in my phone for several days waiting for the ideal moment to read it. It was just now and it was just so fucking worth it. Always impressed.

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