My “Perfect Match” & I Broke Up, & It Changed How I Thought About Compatibility

In my late twenties, a mutual friend introduced me to the girl I knew, with all the conviction in my by-then-highly-experienced, late-twenties heart, was The One. 

E. was the first person I’d come across, let alone dated, who shared my passion for biking everywhere in New York. She was also an even more committed gourmand than I was. Those two things would have been enough to seal the deal for me. But there was so much more. We had both grown up in Singapore and then gone abroad for college, so understood what it was like to be raised in one place and come of age in another. We were both lawyers, so appreciated the long hours the profession could require and that pedantry had its virtues. And, of course, we shared a favourite band. 

When we broke up two years later, after she moved back to Singapore and eventually told me the distance was too difficult and she didn’t think things would work out, I was devastated — not only about losing her, but also losing the idea of her. This was it: I was never going to meet someone who I was so compatible with again. 

Up until that point, it always felt vitally important that I find someone who shared my tastes, my interests, my frames of reference. On a practical level, engaging in activities you both enjoy is fun — so the more overlap there is, the more fun you have. Also, having a common background or experiences gives you a shared vocabulary and understanding of those aspects of your lives. On a hopeless-romantic level, it feels like the stars align when you find someone who shares a passion for something you find meaningful, whether that’s a coming-of-age novel or an indie musician. We define ourselves, to a significant extent, by our tastes and preferences and interests. When someone gets them, we feel like this person can really, truly get us, too.

So, when the time came to start dating again — since the alternative was a lifetime of solo cycling on the West Side bike path and sending Serious Eats article links to friends who probably wouldn’t even click on them — I went to the internet.

This was the heyday of Match.com and eHarmony and OkCupid, of filling out questionnaires and composing profiles about who you were, your interests and activities, what music you listened to or books you read, your ideal first date, your favourite restaurants or travel destinations. I had previously dabbled in online dating — a couple of years prior to meeting E. — but coming back to it now, I was heartened by how many more people appeared to be giving it a try. Match required a paid subscription, and eHarmony hadn’t yet caught on to how lucrative the LGBTQ online-dating market could be — so I went with OkCupid.  

In my searches, I scoured other girls’ profiles for indicia of compatibility, and I littered my own profile with Easter eggs that only a potential soulmate would be able to find. Once someone asked if my profile name was a reference from Salman Rushdie’s Midnight’s Children (it was!) and I practically swooned.

I did meet the next person I dated on OkCupid, six months after E. and I broke up. From the start, though, I worried that my new partner, W., and I weren’t compatible enough, and certainly not the once-in-a-lifetime way that E. and I had been. OkCupid agreed, deeming us a 70% match. 

W. was a mechanical engineer. I’d never known a mechanical engineer, but it seemed like they might be dull. (Afterward I learned she had had the same concern about me, a lawyer who wanted to be a fiction writer.) None of our stated interests overlapped. She looked cute from her photos, one of which showed her mysteriously entangled in packing tape. But did we have anything in common? Would we have anything to talk about? I supposed I could always ask her about the packing tape. I came this close to not messaging her, but at the time I was taking the approach of casting the net as widely as possible. I wasn’t trying to find another love of my life; all I wanted was to meet new, and hopefully interesting, people.

I still remember that moment on our first date when I thought: This is such a cool person. We were talking at dinner and W. said, “... when I was in Antarctica.” Once I confirmed she was referring to the South Pole and not, say, a gimmicky cocktail bar on the Lower East Side, I asked what she was doing there. It turned out she had spent three months at McMurdo Station working on a project for the Army Corp of Engineers. 

Over the next several months, and then years, W. and I continued to learn about all the ways we aren’t exactly compatible. She refuses to bike on the streets of New York, she thinks theatre is boring (she finally told me after she saw a future of fortnightly play-going ahead of her), she doesn’t read literary fiction, she finds my taste in music hopelessly twee. I have no interest in programming, woodworking or mechatronics, and no idea what she does in her workshop in Gowanus on the weekends — motors are involved, and something called a CNC mill. 

And yet, despite our differences, we’re still together. She still does and says things that make me think, This is such a cool person. We make each other laugh (and also furious). I no longer fear that we’ll ever run out of things to talk about. She’s gotten me into crosswords, and I — with an assist from pandemic-related gym closures — have gotten her into running. More importantly, we’re both fully committed to the life we have with each other — whatever challenges we may face, we know we will find solutions together. 

Not too bad for a 70% match on OkCupid.

Online dating platforms encourage us to view compatibility as a quantifiable goal: through ratings that purport to tell you how compatible you are with another subscriber, and with their emphasis on aspects of the dating experience such as interests, activities and tastes.  Today’s dating apps are much more sophisticated than the websites I used years ago, asking users to link their social media accounts to their dating profiles so they can leverage on all the information we already put out there about what we like to do and where we like to go – for example, Tinder has partnered (pun unintended) with Spotify to help its users make matches based on their music tastes. You can also use specialty apps to target people with the specific interest or commonality that you believe your partner should have, from music (Tastebuds) to mindfulness (MeetMindful), fitness (Sweatt) to food (Dine).

I’ve come to think that the idea of compatibility that feels so intuitive to us, and that these sorts of online dating platforms perpetuate so well — what two people have in common, whether they share interests and activities and tastes — is really a red herring. There’s no foolproof way to determine with whom we’ll be able to, as Merriam-Webster puts it, exist together in harmony. We all know couples who we bring up to illustrate the maxim “opposites attract,” as well as couples of whom we say “they have so much in common.”  To focus too much on whether a potential date checks certain boxes could prevent us from saying “Sure, why not?” to the new person who may open up our world.

Not that I’m ruling out the possibility of a future where dating apps’ predictions of 100% compatibility can be backed by a 100% rate of relationship success, because I’m sure stranger things have happened.  Until then, though, the true promise of contemporary technology in finding love may be simply this: that it gives you the chance to discover that you can be with someone you never imagined you would be.