“What would you like to experience for the first time again?”

“What’s the greatest gift you’ve ever given someone else?”

“Would you rather live in a house made of chocolate, or a house made of cheese?”

Many such icebreakers reside in my rather poorly organized Google Drive, hidden within a document titled “36 questions to induce a (hopefully) good convo by chels.” When I first read the viral New York Times article on 36 questions that could supposedly lead to love between complete strangers, it materialized something I’d felt I needed for many years of my life: some sort of formulaic, step-by-step process to intimacy and better connections. Over winter break freshman year, I wrote my own list of 36, aiming for lower stakes but higher quality conversations. “Don’t do all 36 at once,” I’d emphasize, every time I gently forced other people to do this with me. “Just pick a few, or each person can pick one, and see where it goes from there.”

Since then, my unofficial role in student organizations has been the icebreaker generator. I believe that the way people answer these questions — even the sillier ones! — reveals so much about them. But more significantly, I have this inexplicably intense faith that this habitual sharing and discussing is crucial to forming strong connections, whether romantic or platonic.

It’s embarrassingly on-brand for a Harvard student to have this approach to love. Like somehow, if I could have X number of conversations discussing Y number of “deep questions” over Z number of weeks, I’d be able to plan and develop the connections I wanted. As if somehow, relationships could be worked on like a project or extracurricular activity.

In 2020, nudged into a gap year because of the pandemic, I joined Datamatch as part of their business team. I committed myself to selling this idea that an algorithm — yes, even an algorithm based on answers about Harry Styles fanfiction and the Adams fly situation — could predict love and friendship.

In the past few weeks, I’ve pitched Datamatch, formally and informally, to friends, strangers, restaurants, and sponsors. While attributing thousands of online matches to the Algorithm™ is Datamatch’s snappy, memorable brand, the real magic that leads to the adorable success stories we present on our Instagram is even simpler. No matter the percentage of compatibility assigned, the real success of those stories is the fact that all of them reached out. Every single one of them deliberately chose to click “match,” chose to meet up in-person, chose to go on a second date.

I’m sure most people know that an algorithm can only help you to a certain extent, whether it’s on Datamatch, Tinder, or Christian Mingle. But despite this knowledge, people often don’t make this deliberate series of choices towards something beautiful.

Instead, we worry over whether that beautiful relationship at the end is even achievable, even worth pursuing. It’s also embarrassingly on-brand for us at Harvard to feel like the worst thing we could ever do is waste someone else’s time. Obviously, because we don’t have the free time for things that won’t work out, we label so, so many things as a waste of time — preemptively rejecting possibilities to protect ourselves from disappointment. I’ve definitely apologized for taking up someone’s p-setting hours to continue a good dinner conversation, and I’ve definitely also been hurt (perhaps unfairly) by friends choosing to prioritize their assignments over me.

But even if those idealized relationships aren’t achievable, it’s always worth trying. It’s worth it that we care, and that we stand by our decisions to care. How could that be a waste of time? During the tragic and isolating moments of the pandemic, the one benefit I thrived on was how people were forced to be more explicit about making space for human connection. People I rarely expected to initiate conversations on campus were so much more willing to catch up, and I truly appreciated the collective sense of desperation — and I mean that in the most loving way possible. These initiations began deliberate sets of choices, and I’ve never regretted making that first step, regardless of the outcome.

Still, these steps have to be taken from a place of deep love. No amount of creative icebreaking or statistical analyses can truly ease loneliness if it is not built on genuine care and affection from all parties. With the lessons learned from our time away, I hope that we will deliberately choose to be unequivocal when we love each other, when we miss each other, when we really would rather not do that seminar reading — because it’s worth making time for each other. I hope that we will love each other wholeheartedly, far beyond the systems we’ve designed to aid us in our pursuits.

Is this idealistic and too much to ask from a campus that’s currently going on one-off dates mainly from the promise of free food and the (more vague) promise of scientific accuracy? Maybe. But at least for me, I’ll be working on this — long after Valentine’s Day, and long after our website closes.

Chelsea E. Guo ’24 is a Sociology concentrator in Adams House and a Business Lead of Datamatch.