It’s been five years since the New York Times’s famous Modern Love essay “To Fall in Love With Anyone, Do This” went viral, and was then followed up by "36 Questions to Fall in Love." Of course, asking and answering these questions won’t guarantee true love, nor relationship bliss. And you certainly won’t want to ask them if you’re not feeling any chemistry — most of these questions get rather personal.
Still, half a decade later, this article has pushed many people to reexamine the kinds of topics they broach on dates, especially that tricky first one. Because let’s be real, first dates are weird. Especially if they’re with strangers you’ve only come to know through mutual right-swiping and witty uses of emojis.
Understandably, single people lament their predicament. How do we strike that magic balance of keeping it easy, light, and fun — but also sparking a connection? How do we let our real selves shine, but also keep our guard up in case this person is a ticking time bomb of drama or a master of ghosting? And what can we do to make sure we’re putting our best foot forward, but also make sure we’re unearthing true incompatibilities?
These kinds of real questions put a lot of pressure on single people — so I asked some experts to weigh in. But before we delve into the questions, we need to set two rules before you even go on the date in the first place.
Rule #1: Do not be overly concerned about him or her liking you.
It’s critical that you’re not approaching dating from a place of fear or a scarcity mentality. At the very worst, this sets you up for failure; at the very best, it makes something otherwise enjoyable far more difficult. “The focus is not on whether he or she or finds you interesting… Instead, we need to think how this new relationship will add value to our lives,” explains Genesis Games, LMHC and Gottman-trained therapist. “If we feel uncomfortable with this and focus on fears like being ‘forever alone,’ we will approach dating from a place of insecurity.”
And if we date from this place of insecurity, she explains, the relationship won’t have a chance for a healthy start. We’ll be too afraid to discuss our values and non-negotiables. And, down the line, we may even find ourselves accepting behavior we shouldn’t and go along with things that aren’t good for us.
That said, of course, we want to impress our date. But this should never come at the cost of distorting ourselves, because in the end that will make both people miserable. Besides, usually the best way to impress a date is simply through basic listening skills. Which brings us to rule #2.
Rule #2: Want to be interesting? Make sure you’re listening.
“Conversation should be like a tennis match, being volleyed back and forth,” explains explains Tina B. Tessina, Ph.D., LMFT, and author of eight relationship books. “Being interested in your date is the most attractive you can be.”
So if at any point the questions aren’t sticking, and the conversation is in a lull, make sure to follow up a story with simple nudging questions like, “Have you ever felt like that?” or “Has that ever happened to you?” Or, you can really show you were paying attention and return to something your date said earlier in the conversation. “You mentioned you did theater in college — what kinds of plays were you in?” Or, “You said you love to hike. What are your favorite trails?”
As Dr. Tessina explains, “I think it’s more successful to listen more than talk, as long as you’re not just completely silent.”
That said, here are a few open-ended questions to get the conversation going. Of course, remember that this is a date. You don’t want it to feel like an interview, so try to make sure that the conversation flows naturally.
1. What brought you to this city?
In order to create a connection, we first need a common ground. And what better place to start than the current place you call home? Asking this question also allows you to explore a fair amount of the person’s history — both professional and personal — and might also jumpstart a conversation that explores what they like to do with their time, or where they like to go.
2. What do you love about your job?
Okay, so perhaps they hate their job — and that’s okay. We’ve all been there. That said, asking this question allows them to put a positive spin on their situation. There’s probably at least something they like about their job, or at least the direction they’re headed in their career. Posing the question this way also gives the person a chance to express what they’re passionate about, which will lead to far more richer answers than, “So… what do you do?” A great follow-up questions might be, “What is your dream job?”
3. How often do you see or talk to your family?
A person’s relationship with their family can be one of the most revealing parts about them. Depending on their answers, you’ll be able to discover more about their heritage or culture — or simply how this person speaks about loved ones. Of course, not everyone has a great relationship with their parents and siblings, sometimes for good reason. But listening to how they explain their current familial situation can be very telling.
4. What was the last book you read that you couldn’t put down?
Even if your date hasn’t picked up a book in a year or two, they’ll be able to answer this question. Anyone who can read has come across something that’s totally thrown their world upside down. So this question provides an opportunity for your date to burst with enthusiasm about what they read and why it moved them.
5. What movie could you watch again and again?
Stories bring us alive, and we’ve all got that movie that just gets us. Why does watching this movie feel like coming home to you? Is it the soundtrack? The cinematography? The story? Or is it the good ol’ reliable humor that never disappoints?
6. What was the worst movie you’ve ever seen?
We’ve all watched that cringeworthy movie that is such an epic failure, it should win an award for the sum of its faults. This is a fun question that can add a lot of humor, while also giving you insight into how your date thinks.
7. What’s your favorite way to take in nature?
Most people enjoy the outdoors in some form or another — even if it’s just a cocktail on the patio. Do they like to get far away? Or are they content with a crowded beach? What’s their favorite place to go? Does their experience with nature involve physical activity? If so, in what form?
8. Do you still keep in touch with any of your childhood friends?
Not everyone keeps in touch with people from their early years, but thanks to social media it’s gotten easier than ever. How your date responds might reveal how they value relationships — or may simply describe what they were like as a child!
9. What’s the best dish you’ve ever cooked?
Do they have a signature dish, or are they always cooking up new recipes? Do they adhere to a particular recipe book, or do they google how to combine the ingredients they have in the fridge? Regardless, what was the meal like? And could they replicate it? If the date is going well, this is an opportunity for the date to say something like, “I guess I’ll have to show you sometime…”
10. What made you ask me out or accept my invitation?
This is definitely a bold question. And, depending on the mood on the date, you might not get an honest or helpful answer. Still, fortune favors the brave. And if you ask this question toward the end of the date, it might not only reveal why he or she found you alluring, but will also give them a chance to express their interest — and whether or not there will be more dates to come.
All this said, when comes down to it, finding a partner has nothing to do with the checklists in our head. It has everything to do with the connections we make. We hope these questions help you build a strong rapport with the dates who are worthy of it — while also sifting out the dates who aren’t worth a second.
