I recently turned thirty years old. I had my first kiss when I turned fifteen, so now half my life has been threaded by a continuous push-pull tango with women. With every romantic interest there is a dance of desire and rejection, moves for the other person to catch and play. Dating and dancing are alike – when it’s good, you feel a fluidity and belonging that is hard to surpass.1

But the dancers eventually get tired, maybe by themselves or more directly of each other. Every step has been explored, and the journey of getting to know another person eventually ends. You arrive as one. That is magical, and there may be new things to discover together, but the rush of diving deep with a stranger is long gone. What happens then? Do you keep dancing, or do you head to the bar for a drink, and find someone new to dance with?

As I’ve turned thirty and the notion of long-term monogamous relationships slowly becomes an overwhelming force of gravity in my life, I have been thinking about infidelity. The truth is that I’ve always been somewhat drawn to it. And in our Western, Christian culture, it seems hard to discuss that openly. Despite clear empirical evidence, the mere acknowledgement that monogamy can be difficult seems mostly taboo.

The core issue is that dating short-term and long-term are qualitatively very different. Those who are single miss the serene stability and trust of a multi-year relationship, the peace of sitting around the kitchen table figuring out your tax returns. Married folks miss the head-over-heels intensity and craziness of dating in their early twenties.2 Our public discourse frames this as an evolution where the long-term is superior, the refined version of the short-term. That may well be true, but it is a trade-off between very different experiences. You can’t really have both, and those who try rarely succeed.

I’ve been in many relationships: a few days here, a few years there. In my multi-year relationships, the routine of the dance had me occasionally missing the single life and peeking at other partners, especially as the pressures of true long-term commitment began to mount. That wasn’t a conscious thing, but something I seemed to do automatically. I might run into a cute girl, and instinctively dial up my charm to 11. I would not ask her for her number, but I would do everything short of that – like I’m testing that I still got it, and the way she’s looking at me, I know that if I were to ask her out she would say yes.

I believe these flirtations with infidelity are taboo-ish-but-universal experiences. However, 2020’s dual prongs of isolation and extremely-online-ness have changed the context of sex. With most people stuck at home and their sex lives having fallen off a cliff, it seems that the online public square has become much more sexual. For crying out loud, simping is a part of the national vocabulary now. This is no coincidence.

Remarkably, the personas of online sex work have changed: porn used to be done by strict acting professionals in studios. It seems that the most popular porn now is produced by couples, and women who clearly have boyfriends. OnlyFans is full of them. It’s like we’ve dropped a layer of pretense about the whole thing. Women who have boyfriends produce porn that is watched by men who have girlfriends.3 It’s almost a love square. Abstractly, there’s something about this that feels like wife-swapping with a few steps removed.

The growing prevalence of online sex work, the normalization of simping, horny on main, etc. all feeds into a culture that is more open to the sexual (not necessarily romantic) desire for a person other than your romantic partner. It is in this context that I think about infidelity: lots of people have a combined (1) nostalgia for the parties and one-night stands of years ago and (2) pent-up sexual desire for novelty.4 They may not seek a real change romantically, but their biologies5 leave them hungry for conquest. The changing sexual environment online is opening up and normalizing many avenues for satisfaction here, but it’s stopping just short of allowing that actual, in-person physical moment.

Will this change? The stigmas against infidelity – whether permitted or not – in real life are powerful. The stigmas against infidelity online are blurry at best: partners in couples watch porn and get sexual gratification independently. Wife Guys on Twitter lust after e-girls. Women with boyfriends sell nudes to thousands of male strangers. It feels like the digital and physical worlds may not have differing standards for romance, but they have vastly differing standards for sex.

Traditionally, people bundled the notions of romance and sex into one. Progressives have unbundled the two somewhat – one is possible without the other – but we’re now at a second unbundling: online vs. offline. Online, there seems to be a weird new liminal space of behavior and morality, challenging how we think about sex, and making infidelity blurry in particular.

The open question is how these standards will interplay in the future. Maybe we’ll live in a world where real life remains overwhelmingly culturally monogamous and supportive of the nuclear-family model, but digital life turns into more and more of a polyamorous playscape. It would be a strange world, where certain thoughts about people in three dimensions are taboo, but in two dimensions it’s A-OK.

It gets weirder when you think about the implications of future advances in sex-tech. Like, is masturbation cheating? Most people will say no. Is it cheating to be plugged into your VR Headset while wearing a Stimulatron 3000 Codpiece to have your 57th sexual encounter with your virtually AI-generated partner? Is it cheating when, post-orgasm, that same Siri-voiced partner softly reassures you about your childhood traumas? Beats me. The very norms themselves are in for a rollercoaster ride.



  1. Done poorly, dancing and dating both feel awkward and only heighten your self-awareness and insecurities. Bad dates and bad dances feel like unwieldy objects colliding. 

  2. I suspect that a partial driver of affairs is simple nostalgia. 

  3. There are other cases, of course, but I think this represents reasonably accurately a plurality, if not majority of cases. 

  4. Incidentally, you really see the influence of the internet in how porn has changed between 1990 and 2020. A world of difference: from 90-minute long B-movies with actual plots to twelve-minute shots of three positions with a preposterous and irrelevant setup. 

  5. The astute reader might point out that it’s not just biology, but a whole host of societal, anthropological, etc. factors. I’m willing to lump all of these into one here, though I appreciate that such compulsions are multivariate in their causes.