Trying the Famous NYTimes 36 Questions In Singapore

When I was told to try The New York Times’ 36 questions that lead to love, I was very, very reluctant. I’m someone who prefers to keep my work and personal lives separate. And, come on, finding a guy on Tinder who would be game to do this is probably harder than finding the actual love of my life. But hey, what boss wants, boss gets. 

So off I went, trying my luck on unsuspecting Tinder matches. I carried out various approaches including:

  1. Coming clean from the start and asking if they would be interested.
  2. Carrying out the usual small talk over text before popping the question.
  3. Asking them the first question (Given the choice of anyone in the world, whom would you want as a dinner guest?) without any introduction whatsoever.


The reply was usually a no or “huh”—assuming I even got a response. Most people are not comfortable with appearing in an article on the internet and I totally get it. Those who entertained me usually ended up ghosting at question 11 (Take four minutes and tell your partner your life story in as much detail as possible.) because it’s just weird to type out the story of your life on Tinder to some random girl you’ve never met.

After plenty of misses, I tried a new approach by asking my latest match, Jason*, if he’d like to help me with my assignment in person in exchange for a meal. And bless him, because his reply was “ok sounds interesting enough”.

Set I: Questions about you

We met at a quiet sake bar on a Saturday evening. The first hour was spent talking about random things we’d been texting about. When the conversation started getting dry, I brought up the first set of questions. 

The first three questions served as a warm-up, especially for me, since I’d already answered them a gazillion times with the other guys. They didn’t reveal much about him either, other than the fact that he would want Anthony Bourdain as a dinner guest.

The fourth question, however, kick-started something interesting. His answer to “What would constitute a ‘perfect’ day for you?” involved hanging out with friends. Mine was to be with my family and eating home-cooked food. To that, he asked, “You don’t cook at all?” I replied, “Do you know how hard it is to cook for one person?” Yes, I was bitchy, but I blame it on the alcohol.

He ignored my little jab (a good thing) and told me about how he used to live alone as well and that his ideal dream is “to be a fucking house husband”. This surprised me because my past Tinder dates have always tried to appear masculine and career-driven. 

He also mentioned he enjoys mopping the floor, which I detest, and hates doing laundry, which I love. Of course, I didn’t offer this information because it might have made me sound like this other crazy guy who told me he wanted to BTO with me before we’d even met.

So plus one point to Mr. House Husband for being honest and not trying to put on an alpha-male facade. 

Question 8 managed to get me to talk a bit about my family, a topic I don’t usually discuss with strangers. 

Name three things you and your partner appear to have in common.
Him: Well…we both seem to have decent alcohol tolerance so far.
Me: Uhm, we have both stayed in Bukit Panjang.

While my statement seems generic, it was the first time he heard that we used to be neighbours. That led to a bit of probing, where I revealed that my mum used to stay there after my parents’ divorce. 

Time for question 11, aka the question that all the other dudes ghosted me at. He started with, “Let me try to make this as interesting as possible.” Ten seconds later, “I went to Bukit Panjang Primary School.” 

Jokes aside, he told me about his schooling days, how he disliked the flashy ways of SMU kids but did the same anyway, his hobbies of fencing and fishing, and how he left a law firm to do in-house work because he was completely drained from the feeling of being used as a money-making tool. 

In those 4 minutes, I gathered that this guy is not afraid to try unconventional things, and is really quite a down-to-earth person who’s not all about dollar signs.

Set II: Questions about your relationships

The second set of questions focused a bit more on relationships:

Question 14 (Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?) revealed that he has always wanted to take a train to Vietnam. That struck me because at the back of my head is a plan to take a train from Singapore to London, formulated since my colleagues attempted it two years ago. Had I found myself a travel buddy? It was still too soon to tell.

A few questions down, we shared with each other our most treasured memory. I told him about how my dad used to take me to Haagen-Dazs as a treat. I would be able to order anything I wanted even though we were far from being well-off. My dad would then order the cheapest thing on the menu for himself.

Inspired by my story, he shared the memory of him and his family going for special teppanyaki birthday dinners when he was a child, and how his dad would order a beef set just because he knew it was Jason’s favourite dish. 

While our stories are not unique, sharing something we both could relate to made me feel even more comfortable talking to this person. This could definitely be linked to the novelty penalty, which suggests humans just prefer listening to familiar stories, but at that point in time, all I thought was, “This guy gets me.”

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Set III: Questions about us

It felt as though we went through the questions quickly. But my recording showed that we had already been chatting for 2 hours and 25 minutes. 

It was time for Question 26: Complete this sentence: “I wish I had someone with whom I could share … “ 

I said the first thing that came to mind: food. Let’s be real, the best part of being in a relationship is the fact that your boo can order char siew rice and you can order Hokkien mee and everyone gets the best of both worlds. 

After hearing my piece, Jason laughed and said, “Well, I was gonna say my deepest darkest fear but on hindsight, yours is a very valid statement.” 

Thank you for the validation, but of course I probed into the deepest darkest fear, which turned out to be death. Jason relates sleeping to dying, and shared several stories about how he would wake up in the middle of the night sometimes and think, “I’m alive.” 

Tying it back to the question, he added, “It’s those times that I wish I had someone to talk to.”

Towards the end of the set, I could tell that we were both getting tired of these serious questions. As interesting as it is to get to know someone, we had just spent three hours digging into each other’s lives, and talking about things even our BFFs may not know about. 

That being said, he kept his grouses to himself and answered everything sportingly. “I’m just happy for you that you can finally finish your article lah,” he said, when I told him that the end was near.

Third last question: 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? Why?

His first response was, “Is this some meme or something.” His actual answer was his computer, which he assembled himself three years back. I then introduced him to my chou chou, which has been my loyal companion for the last 20 years, and shared with him stories of my darker childhood days when my chou chou acted as my professional tear collector. 

Second last question: Of all the people in your family, whose death would you find most disturbing? Why?

Even though we’d both, in a tipsy state, lost the ability to speak in proper sentences by then, he managed to express his thoughts on this rather eloquently: 

“Mum lah. Although my mum nags at me the most, if she were to die, [I know] everything will stop and I would feel it lor. This relates all the way back to the first question. Anthony Bourdain. There were many times when I came home, my parents would be watching TV, and they’d be watching his show. After he died, it stopped. At that time slot, his voice no longer echoes from my living room. There are times when I come home and hear someone else’s voice, and I think, ‘He’s gone.’ I always [relate this to] my mum. No matter how much I get irritated with my mum at times, I know that if she’s gone, she’s gone.”

Question 36 aka The Final One: Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

It could be because fatigue had hit home, or perhaps it’s ‘cause we are both drowsy drunks, but we spent a while trying to assemble our thoughts.

I was ready to give up and say, “Forget it lah, don’t need to answer the last one.” But him being a better person than me, started on his final words of this experiment.

Him: This is not really a problem but, like, everyone is getting married so maybe I should get married? Not in an I-wanna-get-married kinda way but more like, in this year, I’ve attended 5 weddings.
Me: So that’s a problem for you?
Him: No lah. It’s not really a problem. It’s more like, where it used to be a negligible part of my mind, now it’s in a slightly less negligible part of my mind.
Me: What, getting married?
Him: Settling down lah. A part of me likes to think, my parents gave birth to me when they were young. My dad is now 60, and my mum gave birth to me when she was 26. And sometimes I think, “How old should you be when your kid grows up?” On a daily and even on an average basis, I don’t give a shit about it. But there’s a small 2% of me that’s like…I need to start thinking about these issues seriously.

I don’t know if this is something he would have told me had this list of questions not existed; after all, settling down is not something you’d discuss with someone you just met. But for some reason that night, I appreciated his honesty. 

Trying The NYTimes 36 Questions To Fall In Love

At the end of the night, I felt as if I knew this guy better than I know my best friend. While there could still be a 0.01% possibility that he’s a psycho who keeps a dead body in a metal pot, the candour that he’d shown throughout our three-and-a-half-hours of conversation was something I liked very much. 

While I didn’t fall head over heels in love that night, I wouldn’t mind getting to know this person better. Do we have a second date? I don’t know yet, but he graciously (and secretly) paid for dinner, which means I still owe him a meal. In other words, he used the oldest trick in the Singaporean Tinder Playbook—good one, Jason. 

*My Tinder date’s name has been changed because I promised him absolute anonymity, so don’t bother stalking! 

Cover illustration by Asher Mak.

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