I played 36 Questions. Here’s what happened

You might have heard of the NYT essay by Mandy Len Catron, ‘To Fall in Love with Anyone, Do This’, or watched her TED talk. I did both, about a year ago, and watched the VICE experiment to boot. I was captivated by Ms Catron’s talk (and results), plus the outcome of the VICE experiment, and wondered if 36 questions was the answer to my dating woes.

For those who are unfamiliar with Mandy Len Catron’s TED talk, and NYT essay, her essay was written based on Dr Arthur Aron’s study, in which he conducted an experiment to see if closeness could be fostered based on asking increasingly personal questions. Two participants in Dr Aron’s original study fell in love, so did Mandy Len Catron. I saw no reason why I couldn’t. I went on a couple of dates and while I met a few people I liked, I didn’t have the courage to broach the topic of playing the 36 question game and consequently exposing all our vulnerabilities in the early stages. And so my curiosity continued to be unsatiated. Until I went to New York, that is.

I had invited myself along to what was supposed to be my friend J’s solo trip. As we are both fairly independent and share little in the way of similar interests, I spent a good deal of time on my own in NYC. On my first Friday night in NYC, I found myself wandering the streets of Times Square on my own, feeling a little desolate amongst the skyscrapers, neon lights and hordes of tourists (myself included). I had had vague plans to meet a bunch of people during my trip which had mostly all fallen through, so after a lonely dinner and a stroll through Times Square, I caught the subway back to Financial District somewhat early for a Friday (9pm!) and went to the local gourmet grocer to see what local delights were available. If I couldn’t have company, at least I could have ice cream.

There was a multitude of cold sweet treats on offer at the local grocery, and I took two tubs of ice cream home and tried both. I was settling into bed when a message from S, 26 popped up on my phone. We had a basic exchange before he asked me out for drinks in an hour or so, and I agreed. I took my time to get ready and in addition to that, I got lost on the NYC subway (for the first and only time) and consequently ended up being 40 minutes late to meet S at Union Square. He was shorter than I thought he would be, but smiled graciously when he said hello to me, as if I hadn’t just unceremoniously kept him waiting for the past 40 minutes.

We started walking and talking and strolled into a bar we passed soon after. Over a few drinks, we exchanged all the necessary and mundane small talk before getting onto more serious topics, such as our past, our dreams, and hopes for the future. S had gone to a prestigious school and previously worked at an investment bank, but was now working on something on his own. He had a youthful, cynical air that reminded me a bit of Holden Caulfield. While I didn’t feel a romantic spark right away, I felt comfortable with him and enjoyed our conversation. During the conversation that first evening, he asked me if there was anything I would change about my childhood if I could. The question seemed strangely familiar and I thought it could be one of the 36 questions, but answered the question without asking him if it was one.

After a few drinks we called it a night, and as he was walking me to the subway station, our hands somehow found each other and it felt like the most natural thing in the world. As we were walking, he turned around and kissed me and then said sorry if he made me feel uncomfortable. We continued walking to the subway, and he asked if I was free tomorrow, and I suggested checking out MOMA. He said he’d be free to see me anytime, and to just text and let him know.

That night, he texted me after I got home and said it was great meeting and he’d had fun. The next day, we met outside MOMA and strolled around the art gallery for a couple of hours chatting about art, life and stuff. I was carrying a heavy bag that day, and still exhausted from the night of drinking prior, I was struggling to carry it. S chivalrously offered to carry it for me, and dutifully did so for the four hours of walking around MOMA.

At 6pm, he put me in a cab to go dinner in East Village, and we made plans to meet up after I got back from New Orleans.

A couple of days later when I got back to NYC, I messaged S asking if he was free for a drink on a Thursday night. He said he was, and we arranged to meet around 9pm in West Village, to have a drink at a bar called Please Don’t Tell. I met him on St Marks Place, where Please Don’t Tell was situated, and we walked down the street trying to find the bar. The bar was hidden behind a phone booth, inside a hot dog place, and the line was sufficiently long already for a Thursday night around 9pm. We watched the couple in front of us enter the phone booth, close the door, and leave. Then it was our turn, and we entered the booth and answered the phone. The voice at the other end asked us if we had a reservation. We replied that we didn’t, and were told it would be a 2.5 hour wait. We retreated in dismay, and walked around nearby looking for a decent bar, without the long wait. There were none.

With that, S said he knew another cool bar called Bathtub Gin, which was across town, so we hopped in a cab and left. We were admitted immediately, and after being seated, we ordered gin cocktails, which seemed most appropriate. As we settled in to the booth and took in our surroundings, S smiled at me from across the table, and I thought about how many times I’d been here before, and how temporary it was. We were engaging in idle banter, when suddenly, S asked if I wanted to play a game. I said, sure, and asked him what kind of game. He began to describe 36 questions, and I realised what he was talking about.

I explained to S that I had the app on my phone, and told him how I was well acquainted with the concept of 36 questions, having watched Mandy Len Catron’s talk on YouTube before, and having been on a reality TV show based around the concept. I asked him if he had played the game with anyone before, and he said no, he asked me if I had, and I said though the show was loosely based based on 36 questions, aside from that, I had never played the game.

And so we started playing the game. Round one, full of interesting and less invasive questions, included things like: “Given the choice of anyone in the world, whom would you want as a dinner guest?” Such things didn’t stray far from the realm of ordinary questions asked on dates. However, the questions got increasingly personal, and as rounds two and three commenced, I found myself opening up to S, telling him things I had never before confessed to even my closest friends and past loves. An example of a round two or three question was, “When was the last time you cried alone? In front of someone else?”

Unlike the intention of the inventor in creating 36 questions, I felt less like I was falling in love, and more like I was consciously unburdening all the things I had built up over the years. I’m not sure how he felt about it.

We were close to the end, and suffice to say, I felt like I hadn’t (figuratively) been so exposed to anyone in such a long time. We only had a few more questions to go, when J called me asking if she could meet me before going to the club together. The club she’d been at was just down the street from where we were, and so she walked to Bathtub Gin, and watched us finish our questions and timed us as we came to the uncomfortable part of having to stare into one another’s eyes, without breaking eye contact, for 4 minutes.

I thought I could do this part easily, but when the time, I struggled. I could barely hold eye contact for 30 seconds, without looking away, while S maintained eye contact, smiling at me all the while. Meanwhile, J was sitting to the right of me, timing the whole thing on her iPhone. S was so disciplined that he didn’t even break eye contact when the waitress came and dropped off the bill.

It was a relief when J said the four minutes were up. We paid the bill, and walked out, and invited S to join us at the club. He took us up on our offer, and the three of us danced awkwardly to some sort of music which genre I couldn’t define. We stayed at the club for a little bit, and when we called it a night, S saw us goodbye in a taxi and kissed me on the cheek, albeit a little close to my lips.

He messaged me the next evening asking if I wanted to drop by his improv night to participate, something to get outside of my comfort zone- it was something I had mentioned the previous night. I replied that I had dinner plans but would try to meet up after. Things got in the way, and I didn’t end up meeting him, and I didn’t see him on my last night in NYC either.

Things did get in the way, but there was no point at which I couldn’t have seen him if I wanted to. The truth was, the 36 questions experiment with S had left me feeling no closer to him than before doing the experiment. It also did not trigger any romantic feelings (any more than what I had already) for him. In short, after doing the experiment, I was ambivalent as to whether I saw him again in the short time span I had left in New York. I was disappointed that the experiment seemingly didn’t work in my situation, and I wondered whether it was due to the lack of romantic chemistry between us, or because I just wasn’t open to feeling anything for anyone at that point in time.

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