53 More First Date Questions
Co-written by Cassie Willson!
I just attended my 10 year college reunion, which made me feel a slew of things - young, old, nostalgic, grateful, and, of course, horny. I recognized a lot of faces but remembered very few salient details, and quickly bored of asking “so what are you up to these days?” Instead, I started opening conversations with a different question:
“Do you have a nemesis here?”
It led to a lot of very amusing conversations, and occasionally to some hot tea (which I will not be sharing here - what happens in Middletown, Connecticut stays in Middletown, Connecticut).
I have become very interested in conversation as a science; particularly how to improve interactions with casual acquaintances. My working thesis about how to converse with people you don’t know very well is this: you should a) ask them specific questions, b) actually want to know the answers, and c) be happy to change the line of questioning, should they be uncomfortable.
I think b) is where people slip up the most. We all have questions that we feel we’re supposed to ask, but if you’re not actually interested in the answer, you won’t ask interesting follow-ups, and the conversation will become data collection.
On the flip side, I think people are sometimes scared of asking questions that stray from the mundane, because of the possibility of weirding out your conversation partner. I think this is born from experience with men intimacy-mining – when a man asks “what’s your biggest fear?” it’s very rarely because he actually wants to know, and more likely because he is a person who thinks he is “deep” and wants you to agree that he’s “deep.” This affliction is comorbid with the desire to cut corners conversationally, so you feel connected to him in a short period of time, so he can convince you to let him smash.
So we don’t want to do that. But if you are actually interested in learning something about the other person, I’ve found that people respond very well to being asked odd, specific questions.
This is why Amy Poehler is, in my opinion, such a good interviewer; maybe she’s just a phenomenal actress, but when you listen to Good Hang, you get the sense that she’s not just doing PR on their behalf, but also asking them questions that she wants to know the answer to.
It can be hard to think of these questions out of the blue, especially in situations like first dates where adrenaline may cleanse your brain of anything interesting to say. And so, I believe it is my solemn duty to regularly provide you all with readily-accessible questions. (Can you believe it’s been over a year since the most recent “first date questions” drop?)
This time, I asked my dear friend (I love the phrase “dear friend,” it makes me feel like a caftannéd old queen wasting away in Palm Springs) Cassie Willson to collaborate on this list; she is without a doubt the biggest champion of the existing questions, and has earned a co-authorship of a new list from sheer love of the game. She also is smart and funny and a great conversationalist, but the only quality I look for in collaborators is how much of a fan of my work they are.
I hope you enjoy these questions - as I have mentioned in previous lists (re-linked at the bottom of this post), these are called “first date questions” but can also be used to waste time on road trips, as Letterloop prompts, or to reconnect with college acquaintances you later find out are universally hated by your peers.
Enjoy!
Prelude: Past Lives
Before I get into the new questions, I’m reposting my “past life” questions, which were featured in this post. I know, I’m obsessed, but they’ve started to replace “What’s the most off-brand thing about you?” as my favorite conversation starter. So just in case you glossed over them, here they are, again:
What percentage of your past lives do you think were male/female/other?
What percentage of your past lives do you think were human?
How many lives do you think you’ve lived before this one?
Are there any types of life you think you’ve lived multiple times?
My favorite part about these questions is that people often have immediate gut responses to these questions, even if they don’t believe in past lives and/or have never contemplated them before.
Okay, back to our regularly scheduled programming!
53 More First Date Questions
In “The Fate of Ophelia,” Taylor Swift references pledging allegiance to someone’s vibes. Whose vibes would you pledge allegiance to?
How do you feel about the word “lover?”
What’s the most objectively good song you can think of?
Are you more interested in outer space or the depths of the ocean? Are you scared of either?
Describe a perfectly ripe banana.
What future age do you think you’ll thrive at being? Why?
Do you have any hot takes related to ice cream?
How comfortable do you feel in a hardware store, from 1-10?
Whose skill set do you wish you had (a specific person’s)?
Do you believe in top sheets? Defend your position.
What’s your most serial killer quality?
If you were guaranteed safety, what historical event would you go back in time to witness?
Do you prize your intellect or intuition more?
Is there a chore you’re territorial about?
What in your city do you want to shoot with a rocket launcher?
Does your family or friend group have a euphemism for pooping?
How are your dresser drawers organized?
What’s your mom’s drink of choice?
How cute do you think your phone number is? How attached to it are you?
What’s your thermostat set to when you sleep? If you had a magic thermostat that didn’t affect electric bills or the environment, what would yours be set to at night?
Is there an ad you keep getting pushed?
What would your magical title be, were you to practice magic? (for example: necromancer, mage, witch)
What’s your best animal noise?
What snack (purchasable at a typical grocery store) would you be most excited to see at a party?
What yearly salary would you need to make in order to feel rich?
If you find two puzzle pieces already connected when opening a puzzle, do you separate them before beginning? If not, how many connected pieces would it take for you to break them up?
What is THE wedding dance floor song?
What’s your least favorite vegetable?
What was your dumbest injury?
What reality show do you think you would be great on?
Would you rather be able to find any object you’ve misplaced or know exactly what’s amiss in your body at any given moment?
If you were a specific type of headdress (e.g. beanie, headband, cowboy hat) what would you be?
What’s something you’d be genuinely thrilled to receive as a gift?
Would you rather cut out sugar or dairy? (if vegan: sugar or alcohol)
When you hear the word “nemesis,” who comes to mind?
Would you rather your face be used for marketing vibrators or port-a-potties?
What animal would your fursona be?
Describe your dream gravestone/death marker.
Do you feel more like a Croc or a Birkenstock? Explain.
How do you eat tuna (if you eat it)?
If you had to/could ride on a corporate float at a parade, which corporation would be the dream?
What’s the way in which you’re the most woo-woo?
If you had to choose a “normal” person and all you could pick to weed them out was their job, what job would you say?
If its true that your greatest weakness is also your greatest strength, what’s yours?
What do you think was a Sliding Doors moment for you?
If you were to transition, who would be the gender blueprint for you?
What aspect of your current life would impress 10-year-old you?
What clothing item you own makes you feel like a cool kid?
What family traditions would you like to pass on to future generations?
You’re meeting a group of strangers for drinks and all you know is the passion that unites them. Do you choose the group of drummers, psychics, or lacrosse players?
Is there an artist whose entire discography you have memorized?
Do you know a set of parents who you think are parenting right? What’s an example of something they’ve done that stuck out to you?
Is there a live performance (artist/band/theater production) you saw that you still think about?
Ask me a fucking question,
Johnny (and Cassie!)
Previous Question Lists:
so good as usual
it’s an honor to be here