Perhaps you’ve seen this click-bait article by now — Mandy Len Catron’s NY Times article To Fall in Love With Anyone, Do This. It revives psychologist Arthur Aron’s carefully designed series of questions to make a couple fall in love. Spoiler alert: Mandy followed the guide herself and fell in love with her partner.
It’s simple: three back-and-forth sets of 12 questions, which are progressively revealing, followed by an intimate four-minute eye-staring sesh. Maybe after reading this, you’ll have the cojones or ovaries to give it a go yourself. The following is my true story from the trenches as the CEO of the dating app Down.
There are two types of people who are flying while single: those who are secretly hoping to meet that dreamy, serendipitous match…and those who are goddamn liars.
I met Hanna on a flight back to SFO from Europe. I was stuck in the middle seat and running on a tweaked-out sleep schedule. She was conked out hard, so I had hours to ponder about the face behind her mysterious sleeping mask. I assumed (hoped) doubled as a 50 Shades of Grey foreplay prop. When she stirred awake with about two hours left in the flight.
I was pleasantly surprised by the woman behind the mask also. We would both later confess that we seriously doubted our own abilities to attract anyone during that flight: she wasn’t wearing makeup (actually a plus in my book) and my dimples were the only redeeming quality on a tired, sleepless face. We bantered for awhile and eventually came around to the defining moment: how would she react when I disclosed that I created “Bang With Friends” and still run the evolution of it, Down?
I could fill a hooker’s black book with the myriad of reactions I’ve had from that revelation, but that’s for another post (coming soon). It turned out, Hanna had a very mature, sex-positive point of view and totally dug my work. We were getting along well, yet she seemed a little distracted. Even so, I couldn’t help but think that it could finally happen — no, not the mile-high club (yet) — I could fall in love on a flight! Admit it: you secretly wish that the dreamboat strutting down the aisle squeezes in next to you in seat 18B. I have a theory that there are two types of people who are flying while single: those who are secretly hoping to meet that dreamy, serendipitous match…and those who are goddamn liars. The hopeful romantic in all of us flutters at the sight of a cute fellow passenger landing nearby.
Fast-forward a month and my phone tickles my thigh — it’s that glorious match notification on Down.
Due to her beckoning post-flight burrito and an admittedly large dose of grogginess, Hanna rushed off the flight without grabbing my phone number. She stalked me down on Facebook easily though, we briefly exchanged friendly salutations, and then went our separate ways, diving back into busy-body SF world. As I do whenever I make a new Facebook friend who catches my eye, I swiped down on Hanna in my app. It’s a good habit to get into — trust me. Fast-forward a month and my phone tickles my thigh — it’s that glorious match notification on Down.
Our first date was steamy. Like a piping hot shower scene with Mila Kunis kind of steamy. We both felt extremely comfortable around each other and shared way more than usual for the typical first date. As the night wound down, she asked me to share my take on this ‘36 questions’ article knocking about. After both expressing some curiosity, we tipsily agreed to try the exercise ourselves on our next date.
Round 1
Maybe I’m a basic bitch…
It began with a dirty martini drowning three olives, and a happy hour brandy. Set one of the questions seemed almost too abstract. From “Given the choice of anyone in the world, whom would you want as a dinner guest?” to “If you could wake up tomorrow having gained any one quality or ability, what would it be?,” these whimsical questions are open to interpretation and are meant to loosen your collective panties.
My answers would change depending on my mood. For example, my answer for #4 may become more grandiose: “What would constitute a ‘perfect’ day for you?” In that moment, I said something along the lines of gathering my best friends from around the world, playing soccer, drinking games, then delving deep into conversations while comfortably dressed in my pjs. Maybe I’m a basic bitch, but that sounds fucking lovely. We powered through the first 12 questions, finishing at 95 minutes, two nursed drinks, and a notch more relaxed.
Round 2: Meet Up For Some Kisses!
We weren’t able to resist sneaking in kisses in between answers, and decided to tackle round three at my apartment
With our drinks reloaded, we dove into set two of the questions. Here’s where they get deeper and some patterns start to emerge. Most answers added some great insight into each of our views on relationships with family and friends. I actually felt like I was repeating myself, especially with my answers on friendship. Still, we bonded on our similarities, like for #20, “What does friendship mean to you?” We both said that friendship means honesty and reliability. Calling us out on fuck ups, celebrating successes, mutually dropping our guards to open up without pretension, and being consistently available — flakiness kills friendships.
This round really built a strong bond between us in other ways, too. We alternated saying five positive characteristics about each other for #22, a great opportunity to stroke each other’s… egos. Plus, Hanna won some brownie points for taking great care with the question about my mom. As she knew that my mom passed away when I was just a lowercase g. By the end of this set, we weren’t able to resist sneaking in kisses in between answers, and decided to tackle round three at my apartment instead of the sleepy bar. Total damage for the second round: 85 minutes, two more stiff libations, and plenty of smooches.
Round 3: Wrap It Up!
I’ve seldom felt so liberated and comfortable, despite the inherit vulnerability of my answers.
We walked hand-in-hand to my place and poured some more drinks; I slipped into my pajama pants, then instigated a visibly troubling dilemma for Hanna by offering a pair of PJs as well. In her own words, “I’m not sure I trust myself to go home soon if I take off my jeans…” She made the right choice and we sat face-to-face in our PJs on the couch in front of the delightfully cozy fireplace.
Set three turned up the heat even more. The first sets of questions prepped us for some doozies, like #26: “Complete this sentence: “I wish I had someone with whom I could share … ” Most of the questions in this set probe deeper than before and cement a level of trust. We shared embarrassing moments in our lives, the last time we cried in front of another person and alone, and what we would regret not saying if we were to die. Finally, we shared a problem we are currently facing and solicited each other’s advice. I’ve seldom felt so liberated and comfortable, despite the inherit vulnerability of my answers.
Round 3: Continuing
After these final dozen questions, we went for the finale — four minutes of gazing into each other’s eyes. We are both the type to make solid eye contact when talking anyway, but this was a whole ‘nother level. We expected the four minutes to feel like an eternity, yet the timer buzzed almost too soon. I could tell the exercise made Hanna uneasy and made it hard for her to concentrate. If you do this on your own, I recommend getting the initial minute or two of giggles, jokes, and funny faces out of the way, then starting your timer. Unlike the original article, I didn’t feel like I was gazing into Hanna’s soul (whatever the hell that means). But we definitely grew more and more anxious to end the exercise and get started on exercise of a different type…
So, what’s done is done. After completing the 36 question quiz and the staring contest, I’m happy to announce that I’m getting married!
… Just not quite yet. Most people tell me that they expect me to be a bachelor late into life, living the oft-assumed crazy lifestyle of the CEO of Down. The truth is that I’ve always wanted to get married, but I approach marriage with an abundance of caution. Take a large heaping of divorced parents fighting for years, add in a generous amount of cynicism from seeing peers’ marriages fall apart, and top it off with a pinch of doubt in monogamy’s place within Western cultures — What you get is the perfect recipe for matrimony skepticism.
Yet, I’m looking forward to forming a lifelong bond with an extraordinary partner: taking care of each other, growing with each other, and devoting our lives to becoming the best versions of ourselves, together. I am getting married — someday. For now, I’m not sure where Hanna and I will take our nascent and undefined relationship. But, I’m already grateful that we shared so openly and deeply. With some help from this silly guide to falling in love.