Now is the season when hearts and minds sync up — online. From the winter holidays to Valentine’s Day (February 14), dating sites experience a 30% increase in signups, millions of photos are uploaded to, and an estimated 1 million dates will happen in the U.S., according to data published by MarketWatch in 2018. What are the chances that all those fledgling couples will make it? Philosopher Skye Cleary — adjunct lecturer for the Athena Senior Seminar at the Athena Center for Leadership — contemplates their fates. 

Skye Cleary bookA researcher in how philosophy affects life and the different ways that people understand romantic love, Cleary has extensively explored and written about both subjects. Cleary co-edited How to Live a Good Life: A Guide to Choosing Your Personal Philosophy (January 2020), co-wrote the chapter “Hang the DJ and Digital Dating: Should We Use Computers to Help Us Find Mates?” in Black Mirror and Philosophy (2019), with Massimo Pigliucci, and cast a critical eye on what’s wrong with our everyday ideas about romance in Existentialism and Romantic Love (2015). Currently, Cleary is writing a book about Simone de Beauvoir, the 20th-century French philosopher and theorist. Cleary is also the managing editor of the American Philosophical Association’s blog.

In this Valentine’s Day Break This Down interview, Cleary shares her insights on the philosophy behind romantic love and whether digital dating helps or hurts.

The book Black Mirror and Philosophy considers the science-fiction anthology series Black Mirror through the lens of philosophical thought. Your chapter, “Hang the DJ and Digital Dating,” asks a valid question: Should we use computers to help us find mates? Is there a clear answer?

There is definitely a role for technology in relationships, but it’s ambiguous what form that help should take. In [the Black Mirror episode] “Hang the DJ,” Amy and Frank meet through an online dating app with a 99.8% success rate, meaning that virtual Frank and Amy are pushed through 1,000 simulations. In each of these simulations, the “coach” tells them to go on a blind date in which they flirt and are clearly attracted to one another. The system’s deadline forces them apart and pushes them into other relationships. It’s only when virtual Amy and Frank rebel against the system to be together 998 times that it’s classified as a successful pairing and real Amy and Frank are matched in real life.  

This is such an alluring idea because it promises a quick fix by omitting the time and effort it takes when dating [the wrong people] and bringing people closer to being in loving relationships. And we already have forms of this technology. For example, eHarmony runs a personality and preference questionnaire that gives a percentage compatibility rating on dimensions like intellectual level.  

But the issue is that there is no such thing as an “ultimate compatible other” because people grow and change, and so, too, do their preferences. Even if an app could find a great person, or people, for each person based on past actions, there is no guarantee that relationship will be right for [those same] people in the future. Plus, it would take out a lot of the risk, fun, and mystery of the experience. From an existential perspective, being with others is a process of discovering ourselves. If we leave it up to a system to choose our relationships, it takes away opportunities for people to discover who they are. 

Is existentialism helpful for online daters? 

Existentialism warns about putting too much faith in any system that promises to make our lives easier and happier. On the one hand, it would be such a relief if we could have all our relationships mapped out for us. On the other hand, submitting to a system like that would relieve us of the responsibility of being self-determining agents of our own lives. Leaping into a relationship is always scary because there are so many unknowns, such as whether it will last, whether it will change, and whether the other person loves us as much as we love them. Without this risk, there’s less anxiety but also less excitement. For many people, the excitement is worth the risk.  

Do you think the choice to “like” or “pass” that technology gives us offers a kind of freedom?

The question is whether the freedom that dating apps give us is an illusion. Going back to the Black Mirror episode, when Amy and Frank have a conversation about life before the system, Amy says it must have been “mental” to have to work out your relationships for yourself, and Frank agrees. People were so overwhelmed with choices that they ended up with “option paralysis.”  

The main issue is that in swiping, people are making snap judgments based on airbrushed and filtered photos. The premise for attraction is physical attraction, and that comes at the expense of factors that make for long-term relationships, such as good conversation and doing things together that both people enjoy. I know that ideally comes later, but a system based on swiping as the first gate to a relationship doesn’t take these more nuanced factors into account.  

If we should question the world of online dating, how do we explain it when it works?

People had real, long-lasting partnerships before online dating, too! There is a lot of value in online dating because it creates opportunities to meet and socialize. However, if people care about the course of their lives, then it’s important to question how much power they give away. “Hang the DJ” raises the question as to how much control we should give online dating sites to determine who we should love. After all, relationships are complicated, and people are more than what can be distilled into a personality quiz. Just think: How often do people say that the person they were matched with was ideal on paper, but when they met in person it just didn’t work out? At the end of the episode, when the real Amy and Frank approach each other in the bar, “Panic” by the Smiths plays in the background, with the words: 

Burn down the disco, hang the blessed DJ 
Because the music that they constantly play, 
It says nothing to me about my life.

This, to me, is optimistic because it suggests that perhaps Amy and Frank know that neither of the systems that they’re involved with — the app controlled by “the coach” and the disco controlled by the DJ — tells them anything meaningful about their lives and their futures.  

Where do you see online dating heading in the coming years? 

I don’t know, but my sense is that we’ll lean harder into the digital world. I just hope that people stay vigilant about the risks of technology, know that love is inherently risky, and put their black mirrors down every once in a while to interact in real life, have real-life conversations, and make genuine connections. 

Barnard experts explain.