Everyday Living February 13th, 2017

We Tried It: 36 Questions To Fall In Love With Anyone

It all started in a Waffle House, where I asked a stranger to fall in love with me.

We were typical millennials who met online and found the other person interesting and/or attractive enough to meet in person. I was uncharacteristically nervous; I hadn't bet on him being quite so witty (my weakness) and more handsome in person (seriously, when does that ever happen?)

Unbeknownst to him, I had an ulterior motive for this meeting. My struggle was simply finding how to ask him.

I wasn’t jumping in blindly. I had checked off the big things first: Leeroy Jenkins (an alias for this article, which he very specifically chose for himself) and I had been raised in similar backgrounds, so we shared many beliefs and values. We talked and joked easily, each of us understanding the other’s sarcasm and sense of humor. He was also big into Harry Potter, which made him practically perfect on paper.

"How brave are you?" I asked, feigning confidence.

"Yes," Leeroy said definitively, without looking up from his waffle.

"Yes?" I was confused.

"Yes," he looked up. "Whatever it is you're wanting to ask me to do." Leeroy shrugged and smiled, "Let's do it."

Witty people are the absolute worst.

"It's the 36 Questions," I said this warily, trying to gauge his response. He just looked at me curiously. "It's a scientific study that claims two complete strangers can fall in love in 36 questions."

I explained how The New York Times author Mandy Len Catron had tried the experiment and that subsequently she and her partner had fallen in love. The test calls for two people who have never met before to ask each other 36 questions. The questions are divided into three sets. At the end, the partners are supposed to silently look into each other’s eyes for four minutes.

But there was a hitch in Mandy’s experiment that had always bothered me: she had met her partner prior to the experiment. The study specified that the two people should not have met before answering the questions. The other qualifier, equally important, was that both parties had to be open to the possibility of falling in love. I explained to Leeroy that, since we had just met, I wanted to try the experiment and write my own article about the experience.

“Let’s do it,” he was smiling and seemingly unfazed.

“Really? You don’t think I’m trying to trick you into falling in love with me?”

“Nah,” he brushed the possibility off casually, “That’s what I’m trying to do to you.”



One month later, I’m again sitting and laughing with Leeroy. This time we’re 500 miles apart and using video chat.

“It’s not the questions that make people fall in love, it’s the answers,” he tells me. “You ask a question and it’s the answer that can make you think, ‘Man, this person is an idiot. I hate them.’ Like, basically what I was feeling the entire time you were talking.” He smiles at me wickedly.

“Rude,” I feign being offended. “But, honest. And honesty is what I value most above all.”

“I’m kind of a jerk. Maybe you should value kindness a little more.”

“I know better than to expect that from you,” I quip.

“Well, OK,” he replies, “As long as there’s no expectation.”

We can go on like this forever.

Leeroy just got home from his 12-hour shift at the hospital. He looks weary and handsome. For the hundredth time I think how lame it is that he lives so far away. I’m getting Leeroy’s take on the 36 Questions before I write my article.

While I am determined to write it from a scientific perspective, being both participant and impartial reporter is proving more difficult than I anticipated. I’m awkward as I tiptoe around the question everyone but Leeroy and I have asked: did it work?

“So, what did you think the questions would be?” I ask Leeroy. He takes a moment to consider this.

“I was honestly expecting more romantic kinds of questions. Not that these don’t have some sort of romanceness … romantical … romanticness? I can't think what the word is I’m looking for. Romancical? Romanciticy? You decide,” he laughs.

“I like all of these new words!” I tell him.

“I just expected them to be more of, ‘Describe your perfect date,’ or ‘Describe the woman of your dreams,’ something like that. More about love and less about yourself. Especially such personal things about yourself.”

I tell Leeroy my theory: the 36 Questions are artfully designed like a vulnerability exercise. The partners go back and forth, taking turns answering each question. As each question is answered, trust is being built. As more trust is built, the more we are willing to share. The more we are willing to share, the deeper and more profound of a connection is felt.

“Well, I definitely thought it would be weird and too personal for a first date,” he tells me.

“And was it?”

He pauses. “No, actually it wasn’t. Not in the moment.”

While the questions do get more personal as you go, that’s not enough to lure someone into telling a stranger the most private things about themselves. So what is it?

I pondered this at length over the last month. Leeroy and I weren’t the only two people to have experienced a connection after the exercise; therefore, Leeroy’s pronouncement that it was the answers didn’t pan out. If the answers varied per couple, then it had to be the constant: the questions.

After more research than I’d like to admit, I found my answer: turns out, the questions are where the science comes in. They are deceptively innocent, and quite sneaky. The three sets of questions take the partners through three levels of intimacy, or, more specifically, three levels of the brain.

That’s right; this isn’t just feelings. The process of going through the 36 Questions is actually a play on our biology.

Simon Sinek is a well-known author and speaker whose initial fame came from the discovery of what he calls, “The Golden Circle.”

“If you look at a cross section on the human brain,” says Sinek, “looking from the top down, what you see is that the human brain is actually made of three major components.”

“The outermost part of our brain is our neocortex, which is responsible for all of our rational and analytical thought. It’s also responsible for language. The middle two sections make up our limbic brain, which is responsible for all of our feelings; feelings like trust and loyalty. It’s also responsible for all human behavior and all decision making. However, it has no capacity for language.”

Sinek explains that our brain functions from the outside in: we try to do everything we can with the neocortex, as it takes less emotion and energy. (e.g. Q: Do you want to get dinner? A: OK!)

The further you go into the brain, the more you feel (e.g. Q: What do you want to eat? A: Umm … I want some steak and potatoes.)

What you feel also becomes more difficult to describe. You have to really think about the answer. (e.g. Q: Why do you want steak and potatoes? A: Well, I feel like I need something heavy to really fill me up. I’m feeling low on energy.)

“You said several times that the questions seemed to be repeating themselves,” I remind Leeroy, “but if you look at them, they never really did.”

Leeroy thinks about this for a moment. “They technically didn’t repeat themselves, but they kept hitting on the same issue.”

Dr. Arthur Aron, the scientist who originated the study, was using these three levels of the brain to trigger intimate conversation and the feelings controlled by the limbic brain. Our mind's instinct is to always give the simplest neocortex answer. But if we’re asked to look at something a second time, we go deeper. A third time? You are somehow revealing things that even surprise yourself.

“The more personal the questions got, the harder and harder they became to answer. As we went along, they definitely took more thinking,” Leeroy said. “I actually liked how the questions forced me to look at myself. I had to do that a lot more than I expected, which was good. It even helped me answer some questions regarding the people around me, and how I really feel about some things.” He cements my theory.

But if the questions trick us into activating our limbic brain, does that mean the connection and feelings aren’t real?

I hit him with the question: “Do you think that two people who didn’t know each other and who did the exercise, would they be building an artificial relationship? Or, do you think it would still be genuine?”

He thinks about this for a moment, “Artificial in the sense that I feel like trust, respect, loyalty, things that really define relationships, are based in experience. Looking into someone’s eyes for four minutes isn’t really experience. It’s not like the experience of being with them and getting to know them.”

I wince internally. It was the answer I expected, but it was still hard to hear.

“… But I would actually say it’s both. It’s also genuine as it starts a base for a real friendship or relationship. You know these things about this person, you feel something and there’s a connection. And trust is where you want to start,” Leeroy finishes.

So, is it real? Yes, to a degree. Science doesn’t invalidate the feelings or the experience. Choosing to be vulnerable and allowing yourself to feel is key. The participants can still get up and leave during the questions; but if they choose to stay and be present, they are likely to go on an emotional journey that connects them to the other person, as well as themselves. Regardless of how our brains get us to a place of trust and connection, we still get there.

And Leeroy and I got there.

But here’s the thing: first dates are not when couples should be talking about relocating. First dates are for laughing, developing mutual attraction and discovering that you enjoy being in that person’s company.

“OK, so I have one final question,” I start. “You may recall that I predicted the experiment wouldn’t work because I believe falling in love is a choice. The 36 Questions can’t make someone fall in love. But I was curious if you thought the experiment wouldn’t work?”

“Who said it didn’t work?” He interjected, looking at me. “Or are you?”

“Am I …? No, I was just wondering what your prediction was before the questions. Did you think it wouldn’t work?”

“Not necessarily; I’m with you. I think love’s a choice. Most of the time. Sometimes I think you subconsciously choose to fall in love even though you’re trying not to. And that would be when it’s not a choice,” he leans forward so his eyes are wide and Bambi-like on my computer screen. “But it really still was.”

I laugh, “Awww, you’re so cute!”

He sits back. “You’re so beautiful,” he says simply.

He means it.



I’ll save you the diatribe on the complexities of love and how difficult it is to define. Instead, we’ll focus on the real question: do the 36 Questions work?

On a scientific level, yes. All of the feelings and connection we feel when falling in love were there. I believe it’s safe to say that any two people, strangers or not, would feel a greater connection and regard for each other after going through this process.

But in real-world practice?

The 36 Questions warp speed two strangers into intimacy and vulnerability before they know whether or not a relationship is even possible.

Leeroy and I are not dating, but that’s certainly not due to a lack of interest. I credit this to distance, our mutual reluctance toward commitment and too much intimacy too soon. Yep, I think the exercise actually inhibited us. It made the relationship seem more serious than it was.

What should have been something new and experimental became something with a sense of urgency. It made the DTR (“define a relationship”) seem immediately necessary as opposed to us taking the time to discover what made us a good match.

If you decide to embark on this challenge, I give you this warning: you can answer all 36 questions, be honest and open and create trust, but once that’s done, you may look around and realize that deep intimacy and understanding isn’t really everything.