AI Matchmaker: Why Romance Algorithms Fail

by Ahmed Ibrahim

AI’s Uncertain Promise to Rescue Modern Romance

Despite years of swiping, many daters are disillusioned, and a wave of apps are turning to artificial intelligence to offer a more “thoughtful” approach to finding love. But can an algorithm truly replicate the unpredictable spark of human connection?

For too long, the experience of online dating has felt…empty. users report evaluating potential partners based on superficial criteria – a few carefully curated photos and brief bios – while simultaneously feeling judged themselves. Now, Whitney Wolfe Herd, founder of bumble, believes she has a solution: “the world’s smartest and most emotionally intelligent matchmaker.” She’s talking about artificial intelligence.

The dating app industry is responding to a clear signal: customers are experiencing burnout and dissatisfaction. A growing number of platforms are attempting to function as a “personal shopper” for romance, leveraging AI not just for profile optimization, but as a sophisticated matchmaking tool. Wolfe Herd’s forthcoming app will reportedly ask users detailed questions and then utilize a large language model to identify compatible matches, prioritizing “shared life perspectives and values.”

This isn’t the first attempt to quantify love. For decades, dating services have relied on questionnaires and algorithms to predict compatibility. But the results have often been underwhelming. OkCupid, for example, once boasted of its scientific approach to finding better matches.

In 2013, OkCupid conducted a series of experiments that revealed a surprising truth: whether the site deemed two people compatible mattered less than whether it told them they were. Pairs informed they were highly compatible were more likely to continue chatting, even if the algorithm initially assessed them as a poor match. Remarkably, the content of profiles appeared to have minimal impact; evaluations remained consistent even when profiles lacked any written text. Removing profile pictures, though, drastically reduced site activity. as one of OkCupid’s co-founders concluded, “OkCupid doesn’t really know what it’s doing. Neither does any other website.”

While today’s questionnaires are more sophisticated, a fundamental challenge remains: romantic compatibility is largely a mystery. People tend to gravitate towards those with similar demographics, but predicting attraction based on personality, tendencies, and “values” – a notoriously vague concept – has proven elusive. As one psychology professor noted, a real-life spark is often unpredictable, hinging on chance encounters and resonant conversations.Ultimately, the only definitive test of chemistry is a real-world meeting.

psychological frameworks, such as attachment theory, are being incorporated into these new AI systems. Research supports the idea that individuals exhibit varying tendencies toward “secure attachment” – characterized by trust and goodwill – and insecure attachment, manifesting as either anxiety or avoidance. though, even this understanding has limitations. Securely attached individuals are relatively rare, and the dynamics between different attachment styles can be complex and challenging.

The core issue isn’t simply categorizing people into attachment “buckets,” but recognizing that romance doesn’t operate according to a calculable equation. Understanding one’s own tendencies and those of others can be valuable for self-reflection and navigating relationships, but it doesn’t guarantee a perfect match.

Some of the proposed applications of AI in dating even veer into dystopian territory. Wolfe Herd has predicted a future where an AI “dating concierge” handles the entire courtship process, replacing the vulnerability and excitement of human flirtation with automated interactions. Even for those wary of such a scenario, the allure of a “perfect” algorithm promising a “perfect” partner is undeniable.

However, the success of a relationship isn’t solely determined by who you find, but by who you are. Principles like attachment theory are best used for self-awareness, as you have more control over your own behaviour than that of a potential partner. And, perhaps more importantly, woudl anyone truly want human connection to be so easily deciphered by a machine? For now, love remains wonderfully, frustratingly unpredictable-which means finding someone will often remain, much of the time, a pain in the ass. It also means that when a connection is made, it will be so distinctive that no one ever could have predicted it.

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