40 More First Date Questions
That's 100 questions! For free! You're welcome.
Four years ago exactly, I published a list of “33 Actually Good First Date Questions,” which I wrote with my friend Liz Roche. Two years later, I published a list of 27 more, this one co-written with my friend David.
If you were too lazy to click those links, here are some of my all star draft picks (is that a thing?):
What’s the most off-brand thing about you?
What phase are you in?
Are there any songs that transport you mentally somewhere when you hear them?
What’s something you recommend so often that you deserve commission on it?
Do you think your parents are in love?
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)
As mentioned in the preface of the last list, I published these questions originally because I was underwhelmed by the questions I was being asked on dates/dating apps, but I’ve since learned that people have pulled them up in a variety of situations, including car rides with friends, dinners with significant others, and when bragging about their creative, intelligent, and fashion-forward friend Johnny (I assume).
As we all hurdle toward the apocalypse, I thought some new questions were in order, and I am pleased to present those to you today. These 40 make a grand total of 100 questions, so you really have no excuse to sit in awkward silence with anyone ever again.
I would also like to take the time to remind men that after you have answered a question, it is polite to ask “how about you?” or even ask a new question! I don’t know why we are still having trouble with this. :)
Without further ado:
40 New Questions to Ask on a First Date
If I say the phrase “shrimp dress,” what do you imagine?
Before being sent to a desert island, you’re given a piece of paper and asked to write down the name of one song. The population of the island will be composed only of people who have chosen the same song as you. What song would you put down?
Does your car have a gender? How strongly do you feel about that?
What’s an item you lost that you still mourn?
What’s a song that reminds you of your mother?
You have to get a tattoo right now. What would you get?
You become super famous. What’s your crazy request for your dressing room? (ie: an ice-cold package of matcha-flavored KitKats or a foot massager)
Which celebrity would you unfortunately get along with?
Which celebrity do you love but think you wouldn’t get along with?
What was your first ever email address?
Do you have a list of baby names? If so, describe the type of baby names you like with two words.
What cheese could you eat the most of in one sitting?
What’s the strangest nickname you’ve been given?
What piece of media from your childhood are you most excited to share with a child/nibling?
You have complete say over only one room in a house you’re building. Which room do you choose?
What was the most embarrassing shirt you wore regularly as a kid?
How passionately do you feel about good lighting?
If your name was a verb, what would it mean? (ie “i Johnnyed today”)
What’s the sexiest/most endearing song someone can sing at karaoke?
When was the last time you were given flowers, and why?
If you were being sworn into office with your hand on any book, what book would you choose?
Which of the seven deadly sins haunts you the most?
What’s something that does not come naturally to you but you work at?
What do you hope people think when looking at your instagram profile?
You find a dream home at a great price but the listing says it’s haunted. How does that information affect your interest in living there?
What’s the most liminal space you’ve had sex in?
Which photo of me would you show to your friends to brag about me?
Who’s your most controversial friend?
Do you feel like you spend the correct amounts of time thinking about the past, present, and future?
Do you have a comfort movie? Is it your favorite movie?
Which cousin of yours do you know the least well?
What’s your favorite salad base?
Who do you say is your best friend when asked? Are they the person you communicate with most on a daily basis?
Would you rather that all your plants always be healthy and require no care, or your floors always be impeccably clean?
Do you have any collections? What’s your favorite collection (if multiple)? What’s your favorite item in that collection? And if no: have you ever had a collection?
Who were you ahead of the curve on?
What was the best part of the best wedding you’ve ever been to?
Would you rather have a dial that turns your brain up or down?
What is the best rice-based dish?
What’s the strangest coincidence you’ve experienced?
My current answer to #40 is that I’ve been editing this post for a while, and was going to publish it today when I realized it was the exact 4-year anniversary of the original post. Serendipity, am I right? (So yeah - either that, or the time that I said I was so mad I could strangle a cat, and then a neighborhood cat showed up on my front stoop moments later. (I did not strangle it.))
Hope you enjoyed these! I love coming up with them. Lastly, I’d love to know your all-time draft picks (still sounds weird… can’t be right) of the 100 - if you’re so inclined, comment on the post or reply to this email with your favorites!
Still beating on, a boat against the current,
Johnny
I actually keep my favorites from the previous lists in a notes app so I thank you for this gay service 🙏🏻 I have gotten some good mileage out of "Did you like prom?" and "How would you go about getting Kelly Clarkson’s phone number if you had to?" (magically/coincidentally sequential in your list)