The night I found myself sitting across from a woman who looked nothing like her profile pictures – while realizing I probably looked nothing like mine either – was the moment I truly understood what dating had become in the algorithmic age. Both of us had presented aspirational versions of ourselves: her photos were from seven years and one dramatic haircut ago; mine strategically hid the gradual surrender of my hairline to time and genetics. We were essentially two different people on a date with two other different people, none of whom were actually present.
“You look… different than your pictures,” she said, breaking the awkward silence after our initial mutual recognition of mutual misrepresentation.
“So do you,” I replied, abandoning any pretense we might maintain the polite fiction that we hadn’t both engaged in some creative digital self-editing.
We laughed, ordered another round of drinks, and had a surprisingly honest conversation about the strange new rituals of finding connection through algorithms and carefully curated profiles. It wasn’t a love match, but it was perhaps the most authentic dating app experience I’ve had – one where the artifice crumbled early, allowing two real humans to emerge from behind their digital facades.
I should clarify that I am not, by any stretch, a dating app expert. My stint in the swipe-right trenches came after my divorce five years ago, when I found myself single for the first time since flip phones were cutting-edge technology. The landscape had changed dramatically. Dating, once a straightforward (if nerve-wracking) process of meeting someone through friends or shared activities, had been thoroughly disrupted by technology. Like many aspects of life I once helped digitize, romantic connection had been reduced to algorithms, profiles, and interfaces designed for maximum engagement rather than meaningful interaction.
My introduction to this brave new world began with the creation of my first dating profile – an exercise in selective self-presentation that felt uncomfortably similar to the product marketing I’d done professionally. Which version of myself should I present? Which photos struck the right balance between attractive and authentic? How much of my complicated history belonged in a 500-character bio? I found myself applying A/B testing principles to my own personality, analyzing which aspects of myself generated the most “engagement.”
It was, in a word, bizarre.
My early attempts were disasters of miscalibration. My first profile veered too far toward brutal honesty: “Recently divorced tech executive with custody schedule, mortgage, and existential questions about whether I helped build a digital world worth living in. Makes excellent sourdough bread.” Shockingly, this didn’t result in an avalanche of interest.
I overcorrected with version two, crafting a profile that emphasized my professional achievements, outdoor hobbies I rarely had time for, and carefully selected photos that suggested I spent most weekends scaling mountains rather than debugging code and attending my daughter’s soccer games. This version performed better but attracted people interested in someone I wasn’t actually capable of being.
Eventually, I settled somewhere in the middle – honest but not alarming, appealing but not fictitious. Still, the entire exercise felt like creating a personal marketing campaign, complete with brand positioning and target demographics. The spontaneity and serendipity that had characterized my pre-digital dating life was nowhere to be found.
My most memorable dating app disaster happened about three months into my digital romantic journey. I’d matched with someone whose profile suggested intellectual curiosity, professional success, and a refreshingly direct communication style. Our messaging banter was promising enough that we quickly arranged to meet for dinner at a mid-priced restaurant – the perfect balance of investment and escape options.
When I arrived, she was already seated, engrossed in her phone. As I approached, I realized with horror that I recognized her – not from her dating profile, but from my professional life. She was an investor who had recently declined to fund a startup I was advising. Our rejection meeting had been particularly uncomfortable, with her questioning not just the business model but my judgment in supporting it.
She recognized me at the exact moment I recognized her. I watched the same dawning horror cross her face.
“Marcus?”
“Claire?”
We both reached for our phones to confirm what had happened. Indeed, neither of us had used our full names or mentioned our specific companies in our dating profiles. The algorithm had, with cruel efficiency, decided that the woman who had professionally rejected me would make an excellent romantic match.
“This is…” she started.
“Incredibly awkward,” I finished.
We ended up having drinks anyway, transforming what should have been a date into a post-mortem on the strange intersection of our professional and personal digital lives. She confessed she’d been using dating apps partly for professional networking – something apparently common among venture capitalists looking for early access to promising entrepreneurs. I admitted I’d been using them as a form of social research, trying to understand how the digital tools I’d helped build had transformed intimate human connections.
“So neither of us was actually looking for a relationship?” she asked.
“The algorithm doesn’t care why we’re here,” I replied. “It just knows we both kept opening the app.”
This encounter crystallized something I’d been feeling but couldn’t articulate: dating apps weren’t really designed to help people find lasting connections as efficiently as possible. If they were, they’d optimize for successful relationships that resulted in users leaving the platform. Instead, they were designed like any other engagement-driven product – to keep users swiping, messaging, and returning to the app whether or not they found what they claimed to be looking for.
As someone who had spent years optimizing user engagement for digital products, I recognized the patterns immediately. The intermittent reward mechanisms. The strategic friction that kept interactions on-platform as long as possible. The gamification elements that transformed other humans into collectible cards rather than complex individuals. We weren’t dating; we were playing a game designed by people who once sat in meetings very similar to ones I had led.
My dating history became a catalog of algorithmic miscalculations and digital misrepresentations. There was the woman whose profile suggested shared interests in literature and hiking, but who spent our entire date talking about cryptocurrency investments. The man who claimed to be “recently” separated but whose bitter comments about his ex suggested the wound was still very much fresh. The person whose political views aligned perfectly with mine on paper but who turned out to hold those positions with a rigidity that made conversation feel like a loyalty test rather than an exchange of ideas.
And then there were the ghosts – the matches who disappeared mid-conversation without explanation, the scheduled dates who never showed, the promising connections that evaporated into digital ether. Dating had always involved rejection, but never before had it been so easy to treat other humans as disposable, to vanish without consequences, to avoid the basic courtesy of closure.
I’m not suggesting that dating apps haven’t created some genuine connections. I know several happy couples who met through algorithms, including my former project manager who just celebrated her third anniversary with someone she initially swiped right on while waiting for a delayed flight. These success stories exist, but they seem to happen despite the system rather than because of it.
What’s particularly fascinating is how these platforms have reshaped our expectations around romance itself. The paradox of choice has transformed potential partners into an endless scroll of options, creating the persistent illusion that someone better might be just one more swipe away. I’ve caught myself evaluating real, complex humans against an imaginary checklist, dismissing promising connections because of minor incompatibilities that would have seemed trivial in the pre-app era.
My wake-up call came after a particularly depressing stretch of algorithmic dating – three months, seventeen first dates, zero second ones. I found myself lying in bed one Sunday morning, reflexively swiping through profiles with the same vacant gaze I’d once reserved for social media feeds. I wasn’t evaluating potential partners; I was consuming content. The faces blurred together, each reduced to a few photos and clever quips. I couldn’t remember most of the people I’d matched with, let alone those I’d met in person.
“What am I doing?” I asked my ceiling, genuinely puzzled by my own behavior.
I deleted the apps that day – not in a dramatic declaration of digital celibacy, but as an experiment in reconnecting with more traditional forms of meeting people. I joined a local cooking class. I said yes to more social invitations. I made a point of engaging with the world beyond my screens.
Two months later, I met someone at a friend’s dinner party. There was no algorithm to suggest compatibility, no carefully curated profile to set expectations. Just two people connecting over burnt risotto and a shared appreciation for obscure science fiction. Our relationship developed at an organic pace, without the artificial acceleration of constant digital communication or the pressure to define ourselves within rigid profile parameters.
I’m not suggesting this approach works for everyone. Dating apps serve a purpose, especially for those with limited social opportunities, specific dating pools, or constraints that make traditional meeting difficult. But my experience highlighted how thoroughly these platforms have altered not just how we meet potential partners, but how we conceptualize romance itself.
The dating app experiment taught me something unexpected about technology’s impact on human connection. The problem wasn’t just the mechanics of the apps – the swiping, the messaging, the game-like interface. It was how they encouraged us to commodify each other, to reduce complex humans to digestible profiles, to treat connection as something to be optimized rather than experienced.
As someone who spent years helping build digital systems that promised to make life more efficient, more connected, more frictionless, I find myself increasingly skeptical of applying those values to our most intimate relationships. Perhaps finding a partner shouldn’t be optimized for efficiency. Perhaps the friction of meeting someone in contexts not explicitly designed for dating creates a foundation that algorithms can’t replicate.
Or perhaps I’m just getting old, clinging to romantic notions that predate my own contributions to our current digital landscape. Either way, I’ve made peace with the fact that my most meaningful connections have happened in the spaces between algorithms, in the messy, inefficient, gloriously unpredictable realm of human interaction that resists reduction to profiles and preference settings.
Though I still occasionally wonder about that woman from my first honest dating app encounter – the one where we both acknowledged our mutual misrepresentations. Last I heard, she’d also deleted the apps and taken up community theater as a way to meet people. I like to imagine her finding connection under the spotlight rather than the blue glow of a screen, writing her own story rather than having it written by algorithms we both helped create.
