27 (New!) Questions to Ask on a First Date
A Sequel to a Classic
Hello there!
A quick preface - I suspect some of my new subscribers may be in search of Muppet Pride & Prejudice content. That post can be found here, but stick around! The water’s fiiine.
As some of you know, two years ago I released a list of “33 Actually Good Questions to Ask on a First Date.” Basically, my brilliant friend Liz Roche and I – fed up with the monotony of classic first date questions (“Where are you from?” “How many siblings do you have?” “Why de frick did Kiss Ross punch Chris Ross in de penis?”) – collaborated on a list of more interesting prompts. Much like Jason and the Argonauts employed Orpheus to sing a song so beautiful and loud that it drowned out the deadly song of the sirens, we hoped this list might save our readers from the modern day equivalent to a watery grave (a white man explaining cryptocurrency).
Since publishing, the article has done numbers - I have heard tell that MULTIPLE, possibly even DOZENS of people have opened the web page. Friends have told me they’ve used it on dates, road trips with friends, and… well, that’s it. But how lovely!
At any rate, I decided it was time for a second round of questions, so I partnered with my friend David Carliner to come up with a fresh set. So take a gander, forward this to a friend who’s suffering at the cruel hands of Tinder, and let us know what you think!
27 New Questions to Ask on a First Date
If you were doing EAT PRAY LOVE, in what countries would you eat, pray, and love? (one that you'd like to eat your way through, one that would feel spiritually meaningful, one where you'd like to find a romantic partner)
Did you like prom? Why/why not?
How would you go about getting Kelly Clarkson’s phone number if you had to?
Are you on a “hair journey,” and if so, are you at the beginning, middle, or end?
What’s something you recommend so often that you deserve commission on it?
If you had a full week to just “catch up” on your life, what would you do with your time?
What are you sick of waiting for?
What’s something you’d never be caught dead wearing?
If we woke up tomorrow morning and realized we Freaky Friday-ed, who in your life could I turn to with that information?
If you had 3 spigots to dispense separate (limitless and free) hot or cold beverages, what three drinks would you choose?
Is there something you rewatch annually?
What do your coworkers know you for? (ie, "he's the one who always brings in donuts")
Is there a pop culture moment that shook you up so much that you remember where you were and what you were doing when it happened?
What’s the status of your childhood bedroom?
What’s a business in [your city] that would devastate you if it closed?
If you could have a professional costume designer make you a very high-end Halloween costume, what would you commission?
What phase are you in?
Do you have a favorite recipe? Is it the recipe do you make the most?
Is there an item you really want to inherit from your parents? Will you have to fight your siblings for it?
What would your evil alter-ego wear?
What’s a great dog name you’ve encountered?
In a biopic of your life, who would you cast to play your parents?
What’s a way in which you’ve gotten more conservative as you’ve gotten older? What’s a way in which you’ve gotten more liberal?
What’s a no-skip album for you?
What’s your stance on deleting instagram photos post-breakup?
When was the last time you laughed so hard you cried and why?
What’s something you have memorized?
But wait… there’s more?!
As if 60 questions weren’t enough, I also wanted to include some I stumbled across that I love but cannot in good conscience claim as my own:
Bonus Questions
If you were going about your normal day, how many owls would you need to see before you thought something was wrong?
You’re given three all-expenses paid 1-week vacations. The first with your significant other, the second with your best friend, your third solo. What are your trips?
What’s a job that you just know you’d be great at, even thought you have no experience in it?
If sneezing were to cease and no one were to ever sneeze again, how long would it take everyone to notice?
What’s your favorite thing about being you?
Emily Post says at parties you’re not supposed to talk about politics, dreams, or health. What would you add to that list?
If you could choose, would you have dinner with your great-great-grandparents or great-great-grandchildren?
What celebrity would voice your pet in a movie?
If everyone you’ve ever met was in one room at the same time, who would you look for first?
You’re in the castle when the spell that transform’s Beast’s castle is cast. What object do you become?
Do you think washers and dryers are friends, enemies, or lovers?
These were pulled from the comments section of a tiktok by alliegoneaway and were commented by (in order): allouttamilk, connielemons, rosemaryhallmark, ironmaygan, tylerbrickley, macaroni_cheese67, blackbeardsbeachbar, janineehansen, kristinmpls, oddree13, and slaycolle.
That’s all for today. If you enjoyed this list but haven’t subscribed to my newsletter yet, here’s a subscribe button! Next month I will be solving the mystery of Natalie Wood’s death, so it’ll be a fun one.