I was 12 when I first asked another person on a date.

It was one of the most uncomfortable things I’d done to that point, an act of social theater for the benefit of the three or four male friends who were insistent that an idle crush on someone in our class be formalized into an “date.” It felt like I was being forced to walk a plank before an audience of pubescent boys, asking someone I barely knew to do something that even I didn’t want to do.

But the many armed beast of peer pressure and social expectation pushed me further out until I dialed a number I found in our class directory and asked a classmate to go to a movie (something I had neither money nor means of transportation to do). It was both a relief and a devastation when she said no and then hung up on me.

Nothing that begins so traumatically can have a happy end, and in recent years the grotesque impositions of dating culture have spun out into strange and ridiculous variations. Reporting for Slate, Amanda Hess recounts the efforts of one dating site—The Dating Ring—to merge crowdfunding and Internet dating into a new side business, in which hopeful singles pay to transport potential dates from distant cities to see if love will take root. 

In their own sad way, dating sites exploit the unconscious desire to push back against this mistrustful disengagement by making romance a hobbyist pursuit composed of quizzes, checklists, and unread tea leaves.

The site operates as a matchmaking service built around group dates rather than high pressure one-on-one encounters. After filling out a questionnaire, Dating Ring’s tools select a few ideal potential mates and a group date of four to six people is arranged. As Hess suggests, the airlift operation is intended to help rebalance cities where the dating pool is short on eligible members of either men or women.

Ultimately, the structure reveals how pathologically dysfunctional dating really is. It allows those struggling and failing to find what they want to pay to change everything but the concept of gender-biased, pair-bonding itself. There is a possibility that technologies like a group dating network might help free people from these self-defeating social expectations, which treat exclusive romance as the natural culmination of a happy person’s life.

Yet, we always end up using technology to perpetuate the worst of what already is, deepening our connection to the dysfunctions we presently bear. Sites like The Dating Ring could use their algorithms to show how mathematically improbable it is for any two randomly chosen people to remain happily cohabited for an entire lifetime, offering empirical proof that the fairy dust of romantic self-actualization most people spend a lifetime chasing is fundamentally impossible.

Making big shifts away from such old and familiar fantasies is too much for any one person, but doing difficult tasks that would be too much for any one person is exactly what we need computers for. If romantic compatibility is an imaginary ideal, then it can be had with almost anyone with an active enough imagination, surrounded by a secure and evocative environment.

For years, we have internalized the work of securing our own environments with fractured and faulty structures like sexual orientation, gender identities, family defined through bloodline, and sexual exclusivity as a symbol of commitment. But, all of these assumptions trap us in insupportable arrangements, slowly alienating us from instinctual needs while ensuring we punish ourselves for not being ideal exemplars of the make-believe. 

These technologies all depend on people having been taught to withhold social affection and romantic experimentation from one another on faith that there is a personally-suited embodiment of genetic and dispositional traits waiting out there in the world. In their own sad way, dating sites exploit the unconscious desire to push back against this mistrustful disengagement by making romance a hobbyist pursuit composed of quizzes, checklists, and unread tea leaves.

That dating sites are now literally airlifting potential mates into distant cities takes this idling, mid-afternoon distraction to a slapstick extreme. And undoubtedly, some dream couple will form from this arrangement, and become a media spectacle, visiting talk shows and selling the movie rights to their life story. All the other stories they could have told about their lives will go untold. All the other people they could have slept with, learned from, and shared with will remain spooky strangers, in whose faces a door must be shut in order to secure a fairytale that fits only two.

Michael Thomsen is Complex's tech columnist. He has written for Slate, The Atlantic, The New Inquiry, NewYorker.com, Billboard, and is author of Levitate the Primate: Handjobs, Internet Dating, and Other Issues for Men. He tweets often at @mike_thomsen.

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