The famed ‘36 Questions to Fall in Love’ gained popularity in a viral NYTimes story, wherein two strangers ask each other a set of increasingly intimate questions, and by answering them, you fall in love. The questions are supposed to provoke deep thought and give your date background info on why you are the way you are and blah blah blah. Also, there’s four minutes of uninterrupted eye contact that closes the whole thing, so that’s pretty cool and low key.
I arranged a last minute Tinder date to test out my personal theory: that the 36 questions are bullshit and that people just like listening to themselves speak. I was willing to bet I could wholeheartedly go into the experiment and walk away like I do on most every Tinder date: not in love.
I’m a perfect candidate for these questions because I’m dramatic AF and done apologizing for it. I’ve had one serious relationship and it left me saddled with enough emotional baggage to turn me off the whole thing for a few years. I feel constantly on edge that no one will ever love me, but also egotistical enough that I truly think no one is good enough for me. I’ve been known to pull up zodiac compatibility on first dates. I spend all my time trying to rush people into falling in love with me, but I do it messily enough that I can justify it as self-sabotage when they don’t. I don’t know how to toe the line between conversationally self-deprecating and full-on self loathing, so I usually wind up dating guys who shit all over me and asking for more.
Anyways, this is all to say that I read over the questions and already primed myself to start turning on the tears at #18 (“What is your most terrible memory?”). These questions are corny as hell, I thought. But also, I hope I get to cry during this.
I opened up Tinder, changed my bio to “do the 36 qs to fall in love with me or else” and waited.
Matthew* was a lawyer in his 30s, cute in a Stanley Tucci kind of way… only like 7 feet tall, and most importantly, he was done with the questions (his opening line was about the uninterrupted eye contact). I’m probably emotionally capable of falling in love, I thought to myself before the date as I stuffed my bra with an extra ankle sock (for lift, not volume, and it’s not cheating).
When I arrived, 25 minutes late despite living eight minutes away, I was worried I’d have pissed him off. Not the case! Matthew was a perfect gentleman, waiting patiently by a table with the app version of the questions at the ready. I had also brought along the book like a psychopath, because for some antisocial reason, slamming a hardcover down in a bar feels normal to me.
We quickly realized it was fairest to alternate who would answer first. This was key because as I found out very quickly, it is super easy to feel self-conscious of your answer or worried you answered “incorrectly” after hearing another, much more eloquent response. There was one question where we had to describe what we valued in friendships and I was like, “Uh, sense of humor?” and he had a very eloquent answer about the “goodness of people” and I absolutely wanted to stab myself in the thigh for going for the pothole-sized deep dive with my answer.
There are also several points throughout each set where you have to compliment one another. These were the questions that I had been most afraid of, going into the experiment. Cringe-city! THANKFULLY, it wasn’t that bad. I jumped to start the compliments first, hoping to establish a nice, platonic, “I respect your reasonable desire to find happiness in your work,”-type vibe. Another organic plus of the questions: I felt comfortable and was pleased that things weren’t turning overtly sexual right away.
I learned a lot about Matthew — stuff that I don’t think I would’ve gleaned from his profile or on a first date. But the questions also made potential land mines more visible. He spoke often about his family, and I couldn’t relate. If you aren’t super close with your family, it’s always awkward when other people are. He mentioned that he was someone who liked being alone and had a tendency to drop off the face of the earth for a few days at a time, which is a problem I’ve run into with past relationships. This isn’t to say I’m needy, but yeah, it’s because I’m needy. As much as I love drama, the thought of knowingly signing up for a bunch of unread text messages feels exhausting even to me. If you’re meant to be, the questions might speed it up, but if you’re just not compatible, those differences will come out sooner rather than later.
I didn’t see anything saying we couldn’t talk during the last four minutes of eye-contact so I asked him about dogs while we both tried to not break. Considering we’d just sat through two and a half hours of probing questions, it wasn’t as hard as I thought, but it was still awkward AF. I’m not sure the small talk made things easier, since we both knew whatever superficial dumb questions I lobbed at him about dogs were just there to distract the both of us. It’s like, I’m not actually going to deep-dive into GoT theories with the nurse who draws my blood, but I’ll word-vomit some bullshit just to not see a needle.
Oh, there was also a point where he mentioned that he was a chihuahua person and I think I was mentally like, “we’re not doing this.”
I liked the structure of the questions, but at the end, things fell apart. I couldn’t shake the fact that we were so different. I enjoyed talking, and having a script made me feel like I could relax without having to make any stupid heavy-handed flirty small talk. But the same time, if I was so stoked on not having to flirt, wasn’t that a red flag? The same sexless reason I had enjoyed doing the questions also underlined the fact that I didn’t really feel a ton of physical chemistry.
The worst was when Matthew said he wouldn’t want to do the questions again with someone else. Did I do that poorly that I turned him off the whole thing forever? Also, how humiliating was it that I thought they were kinda fun until he vocalized what a slog they were? After that I was so in my own head I couldn’t even talk like a normal person. He was very diplomatic and assured me it wasn’t personal, but it didn’t matter. I was already spiralling and looking for apartments in another state where I could start fresh.
After the date, I wallowed in self-pity all night. There were a bunch of flies in my living room (the result of a neglected mousetrap or living smack dab in the middle of a bunch of open-air meat restaurants, I’ll never know) and it somehow felt like a disgusting metaphor for my trash-ass love life. Everyone was pouring out of the bars downstairs laughing and having a grand ol’ time, and I was skidding into walls trying to kill flies and then frustration-crying alone.
I felt like a loser in every sense of the word. It sucks when everyone around you is in a relationship and you’ve deluded yourself into thinking that sabotaging a Tinder date is like, some deep psychological power play. Hint: it’s not. Yeah yeah yeah, going into it I was all gung-ho about willingly signing myself up for a potential disaster but after actually trying to seem likeable and normal and having it kind of flop, I couldn’t help but feel a little pathetic. The questions worked in their own sly way and made me way more vulnerable than I would normally be.
A part of me had acted like if I only wanted to, I’d be able to find love in a heartbeat. Except now I was more aware that there was a chance this wouldn’t happen. When you only willingly date idiots and mean guys, it’s easier to pretend like This Is a Choice. It’s harder when you actually try and something just isn’t there. But even just admitting that felt like progress.
As for those dramatic tears I was so looking forward to? I’m sorry to report that I did not get to wow my date with an Oscar-worthy monologue about my lonely childhood. I did of course, frustration-cry later that night when I got home, but like most things, it’s never as much fun when it’s just you.