The moment I found myself staring at a woman who looked nothing like her profile photos—and she was probably thinking the same about me—was when I genuinely grasped the reality of dating in the age of algorithms. Both of us appeared different in very different ways. She was quite literally a different person because the photos used for the date were taken seven years and one dramatic haircut ago. Those of me hid from the camera’s lens surrendering hairline as an entire lifetime of time and genetic violence lurked in the backdrop.
“You look… different than your pictures…” The words behind the first sentence she spoke after solving the awkward moment of silence were rather strange to condition her mind to think of as simultaneously being true.
“So do you,” I said back this time without hiding my indifference towards our futile understandings of wrapping ourselves in the pretense of standing behind some gentlemanly boundaries depicting us cordial.
We exchanged laughter, got another round of drinks, and had surprisingly candid discussions about the newly strange rituals of finding connections through algorithms and carefully curated profiles. While it wasn’t a love match, it was possibly the most authentic dating app experience I have had – one where the artifice crumbled, letting two real humans emerge from behind their digital facades long way early.
To clarify, I am not an authority on dating apps by any stretch. My venture into the swipe-right trenches came after a divorce I underwent five years ago. That set me adrift for the very first time since flip-phones were regarded as cutting-edge technology, which was a long two-and-a-half decades ago. It was striking to see how the world had transformed out there. Technology, I used to work on dating not too long ago, would help streamline the complicated (albeit anxiety-inducing) process of meeting people, friends, friends and shared activities turned into algorithms. Everything had been turned upside down, then. Along with life, love had also been revolutionized and reduced to engagements and interfaces solely designed for maximum interaction, and no meaning.
This contemporary era of technology and social media dated back to the day I created my personalized social media profile as it involved marketing myself to potential partners. It took me in a completely different direction when compared to my professional life as a marketer. Which incarnation of myself should I opt for? Which images struck the modality between appealing yet genuine? Given my convoluted history, how much of my biography could fit in a 500-character snippet? Self-optimizing proposed branding principles whereby I branded myself turned out to be far more complicated than I anticipated.
This, in simple terms, is weird.
In attempts to create a meta-brand, I found myself miscalibrating. With my very first attempt, I registered to multiple platforms with a profile that was way too honest. Today’s newest divorcee of a tech executive gives a custody timetable full of dark anecdotes about a digital society packed with humans riddled by existential dread living in a world about to end paired with a mortgage and baked arms so good he’d beat his mother at the world’s most famous baking competition. Did not surprisingly come flooding results.
Desperately trying to put everything into the box of overcorrection, I made my way to version 2 which simply contained skyrocketed my outlook on life. I hid everything personal and invented new hobbies praising every weekend in my spent debugging months full of children’s soccer aunt and attended games with no daughter available to attend. Only branded to dismantomb up performed allured far better version people attractions wanting a and ridable capable induced to someone pretending rent.
In the end, I landed in the middle of the spectrum – truthful, but not terrifying. Attractive, but not a blatant lie. However, it felt as if I was building an advertising campaign for myself, complete with brand messaging and target audience – which I did not like. I did not enjoy this new digitally driven world because all the spontaneity and chance encounters that defined my life before this period were now absent.
About three months into my new virtual endeavor I encountered one of my worst nightmares. I had a promising match. The profile indicated his career was intellectually stimulating, he possessed an impressive professional background, and he used refreshingly straightforward phrasing. Everything seemed to progress easier than expected and we quickly organized a dinner date at a moderately priced restaurant which I thought offered the ideal balance of financial commitment to recovery routes.
Upon arrival I noticed a woman already sitting down looking quite distracted, glued to her device. To my complete and utter shock, I recognized her. Not from the dating profile photos, not even from casual social media platforms – work. She was an investor from a startup I had been advising, and in fact, had declined to fund. The pitch meeting had been a uniquely painful experience as she relentlessly grilled me on not just the business but my judgment in endorsing such a flawed proposition.
“Marcus?”
“Claire?”
Both of us reached for our phones to confirm what had taken place. Clearly, neither of us had mentioned our full names nor our specific companies in their profiles. The algorithm had most harrowingly decided that the woman who professionally rejected me would romantically pair me with her.
“This is…” she began.
“Incredibly awkward,” I said, finishing her sentence.
Regardless, we had drinks, transforming what should have been a date into a retrospective analysis of the glaring overlap between our work and personal lives in twain digital reality. She admitted that she partially used dating apps for business networking, which apparently isn’t rare among VCs who want a head start to the novel business. I shared that for digital social research—an attempt to grasp the impact of the technologies I helped build on the society’s most basic relationships.
“So neither of us was actually looking for a relationship?” she inquired.
“I provided an answer. ‘The algorithm has no way of knowing why we are here. It only knows that both of us kept opening the app.'”
“I recall the feeling which this particular event made me remember: dating apps were baffling in so many ways that—if they were interested in finding relationships—would be designed to assist in building lasting connections. But as their workings suggest, they seem to be aimed at encouraging users to remain in the apps as long as possible, regardless of whether the users found what they came for.”
“Being in this industry for years, I knew how much effort had gone to the mechanics of rewarding intermittent usage—keeping the user engaged until the last possible moment—stratifying the timeframe of interactions strictly revolving around the used platform—ponit’d forgotten the rewarding parts unused overly a-platform er8ved out only me to er3ve’d encounter sick of Zother mechanisms three The social cards as building even complicated humans baffling in the hands of deeply complicated even to veteran marketers.”
My dating history became a log book of algorithmic errors and bizarre digital forms of identity. Like the woman whose profile claimed she liked literature and hiking but spent our entire date talking about her cryptocurrency investments. Or the man who claimed to be “recently” divorced but whose ex-wife angry comments painted as if he was still emotionally very much in that relationship. Or the person whose political views aligned with mine but were so rigid about them that conversation felt more like a loyalty test than a discussion, turned out did not hold those views as flexible.
And then there were the ghosts — the mid-conversation disappearing matches, the no-shows for scheduled dates, and the seemingly promising connections that evaporated into the digital ether. There had always been some form of rejection with dating, but never like this. People now had the opportunity to treat extermely easy, humans as disposable and vanish without consequence, evade the basic courtesy of closure.
I’m not saying dating apps don’t foster some genuine connections. I have several friends who are happily married as a result of meeting through algorithms, including my former project manager who just celebrated her third anniversary with a man she swiped right on while waiting for a flight. Such success stories do exist, but it seems they happen in spite of the system rather than because of it.
Most astonishing is the way these platforms have altered our expectations for romance as a whole. Potential partners have become an endless scroll of options thanks to the paradox of choice, and the nagging illusion that with one more swipe lies someone better than the last is always present. I have caught myself comparing real, multifaceted people to an imaginary checklist, and dismissing promising connections because of little differences that in the pre-app world would have been seen as inconsequential.
The jarring wake-up moment for me stemmed from a desperate period of app dating working far from my interests – three months, seventeen first dates, none of which were progressed and dated as second encounters. Last weekend, I caught myself lying in bed one Sunday morning scrolling through dating profiles with the same monotonous stare reminiscent of social media scrolling. I clearly wasn’t evaluating any prospective matches; instead, I wasn’t even engaging. I consumed content. Every photo and witty phrase had begun to blend together and I, from a distance, wasn’t able to recall most of the profiles I had matched with, let alone the people I had physically encountered.
“Asking Why?” at least provided me some form of relief, as it comes with an explanation, and the reasoning appears to highlighting the very strange introspective I am having at the moment.
I convinced myself right after this incident to delete the applications that day and two of my mates had been discussing taking a ‘digital detox’. So, I took that step not as an exhausting proclamation to stop ghastly scrolling. I explored the world beyond my screens later on in a more physically engaging manner post my digital detox that simply entailed, gave me truly upgraded focus, albeit it does sound a little complex, it worked – I redirected my focus on a local cooking class to focus on the culinary skills.
I met someone new at a friend’s dinner party about two months later. Unlike modern dating, there was no algorithm suggesting compatibility or pre-meal profiles setting expectations. Simply two individuals bonding over burnt risotto and unique sci-fi . Our relationship was allowed to unfold at its own natural pace, without the need for digital communication or the need to put ourselves into rigid definitional boxes.
That said, I’m not proposing this approach is universally effective. Especially for those with limited social options, specific geographic locales, or constraints that make traditional meeting infeasible, dating apps serve a purpose. But my experience underscored the extent to which these platforms have changed not only the ways we encounter prospective partners, but how we think about romance.
As surprising as it may sound, it was the dating app experiment that taught me the most about how technology ruins human connection. The problem is not merely the app’s architecture – the swiping, the messaging, the game-like interface. Rather, it is the apps’ encouragement of commodified valuing; reducing intricate humans to profiles designed to be simplified and so-called ‘optimized’ as opposed to experienced.
Having spent years assisting in constructing digital systems that promised to streamline, facilitate, and connect life in ways that minimize friction, I find it increasingly difficult to extend those values our most intimate relationships. Maybe, finding a partner is something that should not be optimized for efficiency. Maybe, the friction of meeting someone in contexts not meant for dating, explicitly not designed for dating, provides a foundation that even the best algorithms can’t replicate.
Or perhaps, I’m just getting old and holding onto romantic notions that predate my own contributions to our current digitized world. Either way, I have come to terms with the fact that my most meaningful connections have happened in the interstices of algorithms – the gloriously unpredictable, delightfully messy, ineffably human world of intersection that resists reduction to profiles and preference settings.
Still, I sometimes wonder about that woman from my most honest dating app encounter (the one where we both accepted and acknowledged our mutual misrepresentations). I heard she had also deleted the apps and took community theater as a way to meet people. I like to picture her meeting with people under the spotlight, not the blue light of the screens, forging connections instead of stories dictated by algorithms we both helped build and co-create.
