I Asked My Date The "36 Questions" That Lead To Love And ... Big Fail

Will this supposed magical questionnaire find me The One?

36 questions

In the 12 hours after that New York Times Modern Love blog came out about the 36 questions that can make you fall in love with anyone, ten people sent the article to me. Basically the premise is this: You're supposed to meet with a stranger, ask each other this list of questions - which are grouped into three sets - and then stare lovingly into one another's eyes for four whole minutes. (You can blink - I think?)


Twenty years ago, psychologist Arthur Aron put two straight people in a room in a lab, had them ask each other these questions, do the whole creepy stare-thing, and six months later they were married. (Wow!)

I was intrigued enough to try it myself. I went through my recent Tinder matches and selected a few gentlemen I'd actually be interested in meeting in person (not just the ones that I swiped "right" on under the influence of wine).

After a few matches, a tall, normal-seeming dude responded and was up for the challenge. Before we met, we promised not to look over the questions, so apart from when I first read the article, I didn’t take a peek. For obvious reasons - and three years of pretty ridiculous dating in New York - I was excited to see if something so seemingly simple could work.


But when I saw him walking up to the coffee shop for our date, I knew instantly I wasn’t attracted to him. Per the usual rules of online dating, 6-foot-tall meant 5’9”. And the broad shoulders that appeared in photos, shrunk in person. But probably the biggest disappointment was his voice: it wasn’t sexy or manly or even the voice I wanted to hear for the next two hours, much less the rest of my life.

But I had committed to trying the experiment, so with visions of magical questions turning an ‘okay’ guy into The One for me, we begun the inquisition:

The first set of questions

The questions are meant to get more personal as they go on, so to start, we asked each other the first set, which are relatively harmless queries. Like, whether we’d like to be famous or not, what we’re thankful for in our lives, and what specific quality we wish we had more of.


Since I wasn't that into him, talking to him about his answers didn't feel that intimate, rather more like I was playing a game of 21 Questions with some dude I just met. 

The second set of questions

The second set of questions dove a little deeper and inquired into our family dynamics, which of course, is an important factor in considering a future mate. We talked about our most treasured and terrible memories, we shared a positive characteristic about one another and revealed what we liked and disliked most about our childhoods.

This is the part where I learned the most about the guy across from me: He grew up on a farm, he's super close to his mom, not so much with his dad, he recently just moved out of his parents' house (Yikes! He's 27!), and he doesn't consider himself very proactive or much of a risk-taker. (The opposite of me.)


And though I already knew I wasn't physically into him... this is when I knew it really wouldn't work, either. When I was talking about how close my family is and what I value about how I was raised, he wouldn't let me finish a sentence before talking about himself. The point of this whole experiment is to listen, be vulnerable and sincerely get to know someone, but I think he was more interested in hearing his own (feminine) voice than mine. 

The third and final set of questions

By the last set of questions, which are meant to be the most personal, I lost all hope for the test. The kicker was this specific question: 'Imagine that your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be and why?

In response, I told my date about this really amazing letter that my dad wrote to me when I was three, but only gave to me a few years ago, right before his scary bout with cancer. It's framed on my wall and something that means a lot to me. As I was trying to explain this, he stopped me and said, 'But what about your laptop?' 


Obviously, we have different perspectives on what we consider precious and the way we handle sensitive converstaions.

I’ll admit it. When we finished, I didn’t remind him that we were supposed to stare 'lovingly' into one another’s eyes for four minutes. (And when he told me I owed $20 when the check came, I stopped feeling guilty about ending the experiment early.)

So what did I learn?

A lot, actually. I didn’t fall in love with him (not even close) but I did feel a lot more connected to the conversation and more present in the date itself. If I’m not into someone - or even when I am - I don’t tend to ask the kind of questions that help you really get to who someone is as a person. 


And that’s where the experiment got it right: these 36 questions (or ones like them) will help you quickly understand who your date is and more importantly, if they're a fit for you. (It's funny. Most of these questions I've never asked my best friends, much less a guy I'm trying to date!)

When you're able to discern relatively quickly the type of values that someone has, what they want for their future, and what they like about you (yep, some of the questions asked what attracted you to one another), you get to know the important stuff early on. If single people looking for love got more in-depth than just 'What do you do for a living?' and 'How was last weekend?', we might save a lot of time because in all honesty, most of these 36 questions wouldn’t normally come up until much later into a relationship.

Are the questions personal? Sure. But they aren't so intimate that I felt like I was baring my soul. Instead, they helped me quickly see who my date was without having to wonder if I was being too picky. It wasn't just that I wasn't attracted to him; it also became very evident through this experiment that I didn't really like how he communicated, treated me in a conversation or his stance on certain topics.

My final verdict


I’d do it again - but only on a second date. While the idea of trying these questions with someone you’ve never met is romantic, I think the experiment only works if you already have a crush on someone. Perhaps if I saw a handsome, charming guy from across a dimly-lit bar and started interrogating him while our skin crawled with one another’s fragrance, the whole strangers-asking-each-other-personal-questions thing could work. But otherwise, to have a genuine experience, there has to be an attraction first.

Because no matter what 36 questions you ask, you can’t create love with someone you don’t even, well, like.


Lindsay Tigar is a 26-year-old single writer, editor, and blogger living in New York City. She started her popular dating blog, Confessions of a Love Addict, after one too many terrible dates with tall, emotionally unavailable men (her personal weakness) and is now developing a book about it, represented by the James Fitzgerald Agency. You can find her running along the East River, drinking champagne with her dog Lucy (don’t judge), and constantly tweeting and instagramming.