Credit: Illustration by Zohar Lazar

I started this essay hunkered down in my basement apartment, more or less in hiding as the forces of decency closed in. A few streets away was one woman I'd been dating, from whom I was on an un-easy hiatus. The next neighborhood over lived the other woman I was dating. As the cad in every bedroom farce says: I can explain. I'd been dating the two women for a few weeks – not an unheard-of or un-ethical practice – but after half a dozen dates with each, I got the feeling that it was time to let them know that I was seeing someone else. In retrospect this may have been my mistake. Both appreciated my honesty but informed me that they could not continue to see me as long as I was seeing someone else. Both insisted this was not an ultimatum and got irritated when I called it one.

This ultimatum precipitated a stressful period now known as the Dilemma – a month in which my brain was revved up and in the red zone of the mental tachometer but stuck in neutral. The Dilemma was the first thing I thought of when I woke up, and most nights I lay awake worrying about it. What I should have done was tell both women that I wasn't ready to commit to an exclusive relationship – though this would have meant losing them both. At the last possible minute, inflicting the maximum emotional damage on all concerned, I finally chose one. I had hoped the decision would at least calm my anxiety, but instead I found myself still secretly panicking. Had I just committed myself to an exclusive relationship with someone I hadn't even slept with yet? This did not sound like me.

One of the women in the Dilemma was an editor of young-adult novels who once told me that she got sick of reading about love triangles. "If you really can't decide between two people," she had said in a way that I couldn't help but feel contained some sub-textual message for me, "probably neither of those people is the right one for you." I find this thought comforting and therefore suspect; it's something we tell ourselves to be reassured that our choice was inevitable, foreordained. Hence people's blather about finding their one true soul mate in all the world, even though a surprising number of people miraculously find their soul mate right in their same neighborhood/high school class/socioeconomic bracket. I think the vertiginous truth is that there are quite a lot of people out there you could fall in love with, if you let yourself.

Some of my female friends once explained that being in a monogamous relationship is actually liberating, allowing them to indulge their crushes and flirtations without any of the awkwardness or consequences of actually getting involved with someone. Do I need to say that, in my 47 years, no male has ever said any such thing to me? No two guys have ever commiserated over how much fun hitting on women can be but what a drag it is getting bogged down in all that tedious fucking.


Once, my friend Lorraine was telling me and another male friend of hers, whom I'd just met, about her reprehensible roommate's bringing home a different girl every night. He and I made noises of halfhearted, wistful disapproval. "Oh, come on," she urged us. "You don't really want to be That Guy, do you?" No, we agreed glumly, not really – it was fun to fantasize about, but of course we wouldn't want to be that shallow or manipulative or sleazy. When Lorraine (all names have been changed to protect the innocent and the guilty) excused herself for a minute, the other guy and I exchanged a look.

To any women reading this who may believe that I am speaking here only of a negligible subset of men – the Creepy Guys, the lecherous, unethical ones you wouldn't want to date anyway – I must, with regret, disillusion you: The Creepy Guys and the Nice Guys are exactly the same guys. Nice Guys are simply the guys who have successfully concealed their creepiness. And it gets tiresome and lonely having to maintain this facade of decency in front of all womankind.

Eventually you just want to let someone know the real you and to be able to admit that monogamy is hard – that we are forfeiting something for someone else. Shouldn't the fact of something's being difficult, of its being a sacrifice, make that thing more valuable? It turns out that doing something you don't want to do for someone else's sake is itself an act of intimacy. But it seems as if women don't just want us to be monogamous; they want us to want to be monogamous.

At the same time I was in the midst of the Dilemma, my friend Kevin announced he was separating from his wife. They 'd been together since the early Nineties, one of those couples whose names you always said together as a unit. He'd confessed months earlier that he had a crush on one of his wife's co-workers. I told him, "OK, that happens, don't let it wreck your life or anything. "He immediately set about wrecking his life. When he told me that he was leaving Renee for this other woman, he sounded so matter-of-fact about it that I wondered whether he might have a brain tumor. "I love the way she smells," he said. I knew better than to argue with this.

I referred him to the book I was reading, Sex at Dawn: The Prehistoric Origins of Modern Sexuality, specifically the chapter "The Pervert's Lament," which explains the stereotypical phenomenon of the middle-aged man who suddenly leaves his wife for a younger woman. In midlife, men's testosterone – that cocktail of Viagra, PCP, and Miller High Life that gets us into bar fights, one-night stands, and ill-advised military expeditions – finally begins to ebb, resulting not only in a decreased libido but also in a general lessening of desire. We experience it as a gradual, creeping anhedonia: We enjoy fewer things, and enjoy them less than we used to; and we wonder what the hell happened to us. One thing that reliably boosts testosterone levels is a novel sexual partner, especially a younger one. Which is why so many men who fall in love in midlife rave about suddenly feeling young again, alive after years of dutifully putting one foot in front of the other. It's why such men are often not merely content to keep paramours on the side but must utterly lose their shit over them, forsake their wives and families, wreck their lives, and make pathetic clowns of themselves. Women assume this is silly, trivial lust, but it's driven by something even more primal than sex: the fear of death. Kevin spent a month in the hospital a few years ago; his heart now bristles with stents and he takes fistfuls of pills just to stay alive. The signature tag on his email messages reads, "Consider the finite time you will spend here on Earth before closing this email."

It was in some desperation that I'd turned to pop psychology, self-help, and even clinical literature for insight into this whole mess of sex, relationships, and monogamy. Sex at Dawn is basically an extended appeal to nature, citing anatomical, behavioral, and cultural evidence to argue that promiscuity, not monogamy, was the prehistoric norm among Homosapiens. I found the book re-assuring in a way that made me wary: One should probably temper with skepticism your enthusiasm for a book that conveniently validates your whole sloppy, self-indulgent life as some sort of rational policy.


We're given to understand, from pretty much every source in our culture, that intimacy and attraction naturally go together. But as Alain de Botton points out in his pocket treatise How to Think More About Sex, the ideal – whereby the person you love, the person you have sex with, and the person you raise children with should all be the same person – is a fairly recent invention. In my own experience, love and sex have had about as much to do with each other as looks and brains – overlapping only rarely, by happy coincidence. In fact, they almost seem to actively inhibit each other. I used to think this was a personal problem, or at least a typically male one, but the divorce between love and desire appears to be one of the universal bummers of the human condition. The greatest consolation of de Botton's book is his reassurance that the reason sex and relationships are so difficult is not because you are uniquely screwed up or sinful or weak, but because the two are in fact inherently, insolubly problematic. Each choice involves a compromise: Long-term relationships forfeit the thrill of sexual novelty; sleeping around forgoes the rewards of intimacy.

Ideally, sex should lure you into a relationship with each other long enough for an attachment to form (which, in adults, takes about two years), so that by the time the initial hormonal buzz wears off, you're bonded in a deeper, more enduring way and will spend the next 20 years changing diapers, playing video games, and shepherding kids to soccer practice. As most people know, this system is imperfect. But then evolution did not invent this system to make us happy. It invented it to make more people.

Solutions to this problem have traditionally been rigid and societal, involving measures like arranged marriages, prenups, and stoning. But in the last half-century, they have become increasingly improvised. A lot of people are, in practice, serial monogamists, maintaining a long-term relationship for months or years before moving on to the next – which, since forever is still the ideal, leaves us feeling like chronic failures. Advice columnist Dan Savage is an advocate of "monogamish" relationships, or maintaining primary long-term partnerships, with occasional sanctioned flings or threesomes. And, of course, quite a lot of relationships are secretly, illicitly monogamish – as The Onion reports, "Researchers Find Human Beings Naturally Evolved Toward Monogamy and Carrying On Fun Little Flings on the Side".

It's very hard to get any inside intelligence on marriage from married people. Unless a marriage is heading for trouble and starting to leak secrets, it tends to be a black box from which no information emerges. Most of the marriages I know of are traditionally monogamous; one has a French don't ask, don't tell policy; another is explicitly open and has impressively outlasted many other relationships (but since they've also been directly responsible for the destruction of many of those relationships, they probably shouldn't be too self-congratulatory). I asked my friend Sam, whose marriage to Kayla has endured tragedy intact, for insight. "I think life gets deeper if shared with another mind-soul-body over a long time," he offered. I also know that Sam is a connoisseur of the derrière. We used to have a standing date, on the first warm day of every spring, to roam the streets of New York City, discreetly sightseeing. How does he manage the temptation?

"I love to flirt, and so far it seems I've been able to keep my ogling and flirting to a tasteful minimum, which actually keeps Kayla interested rather than hurting or offending her. I like the dynamic of keeping slightly distant so that you never really are sure if you're going to be able to win your spouse over – that promise of affection and sex isn't an unconditional promise; it has to be won. It's a game, of course. But what isn't?"

He added: "I can't imagine this is helping."

It can be hard to remember, in New York in the spring, why monogamy ever seemed like a good idea. The parade of heartrendingly gorgeous women makes the city seem like a bottomless cornucopia of sexual possibilities. Like most men, I am tormented by the delusion (fostered by the radically compressed narratives of pornography) that for every attractive woman I see, there is some hypothetical sequence of events that will lead to my having sex with her. And I end up damning myself as a coward and a failure the 99.9999907 percent of the times that this fails to happen.

The promise of sex is mainly an illusion. In college, a physiology professor once invited us "to compare the amount of time we spend experiencing orgasm with the time we spend arranging it." How many times have I ever gone to a party or a bar and ended up getting the phone number of/making out with/going home with someone I met there? In all honesty, very, very few. And of those few times, how many turned out to be actually fun? It's mostly not the reality but the tantalizing possibility of sex – reinforced, like an addiction to nickel slots, by the rare, unpredictable payoffs – that gives life its luster.

I'm starting to think that what may be hardest to give up for the sake of monogamy isn't the sex per se so much as a certain self-image that goes with it. I like thinking of myself as single – it means being available, up for anything, faintly dangerous. Undomesticated. Couples, by contrast, seem inert, done. There's a chilling description in David Foster Wallace's The Pale King of young fathers who appear "essentially soft or softened in some way, desperate in a resigned way, their stride not quite a trudge, their eyes empty and overmild with the weary stoicism of young fathers." I once asked a writer I admired, whom I noticed was drinking soda water in a bar, whether he drank. " I'm spiritually a drinker," he answered. "I no longer practice." I wonder if it's possible to do something similar with monogamy, to quit actually sleeping around while somehow remaining "spiritually single"?


We all know how this essay is supposed to end, with the whole problem of monogamy being resolved by – surprise! – the love of one special woman. I will write something like: "I finally get it. It's not some abstract problem; it's about her, loving this one woman I don't ever want to hurt or deceive. In fact, I don't even want to sleep with anyone else anymore. I now realize how shallow and empty my vain pursuit of … " You can fill in the rest. But since it's presumably just us guys here, let's be honest: I have no idea how it ends.

Behavior like my friend Kevin's, or the stereotype of the swinish middle-aged man who ditches his wife for some young chippie, is looked on by most women with a contempt that's ostensibly moral but is clearly more personal. The real offense is not doing harm to others but upsetting the social order; it threatens people to be reminded that their own marriages may not be as stable as they seem, the way the death of someone our own age scares us. (I think this is also why most monogamous people find open relationships and polyamory so obscurely offensive.) Kevin is now pretty much a pariah among his former friends and co-workers, even though both he and his ex-wife seem happier apart than when they were married. Renee has taken up running, lost 70 pounds, and says she's ready to date. Kevin, meanwhile, is already engaged to his new girlfriend, who is forging her wedding ring out of a gold Krugerrand he gave her and makes her own marmalade from Meyer lemons and quinces. A few days ago Kevin sent me a text: "I have to say this midlife-crisis thing has been excellent. I have behaved selfishly, and it has been fantastic. I am happy as fuck."

When people ask me what I think of Kevin's behavior, all I can say is, "It's really good marmalade."

Last year my friend Lucy invited me to a swanky dress-up literary event. There were a lot of young, pretty agents, editors, and writers, all wearing sexy party dresses. It was also one of the few venues where my own meager stock – being a writer – might have any street value. But because I was now in a relationship, I wouldn't be flirting or hitting on, let alone be going home with, anyone. So I had to ask myself, Why was I here? To talk with other writers? To network? Jesus, please. What's the point of swanky dress-up events, or of going out at all, once sex is off the agenda? With that possibility off the table, doesn't the world start to seem denatured and dull?

Later the lights went down and the music got loud and the women started to dance, and I sank into a bitter, self-pitying funk. For reasons as yet unexplained by evolutionary psychology, almost all women love to dance. They also like to pressure men to dance, despite our repeated protests that we really, really don't want to. Maybe it's just a test or an ordeal ritual for potential mates: If you are willing to do something this embarrassing and dumb with the hope that we will sleep with you, there is no end to what you will do. The thing is, though, you can't force people into it; they really have to feel it.

Then the DJ played "I Want You Back," by the Jackson Five. That first ecstatic moan from the throat of Motown's own castrato – who can resist it? Lucy is a married woman with two kids, and notwithstanding a secret crush she had on me when she was 13, we've never dated or even so much as drunkenly made out on New Year's Eve. We had also never danced before. Dancing isn't necessarily an invitation or preliminary; like flirting, it can be a pleasure in itself. It's a ritual pantomime, all bold approach and coy demurral, a way of being open and sensual with someone, without having to give everything away. It's a game, as Sam said. But what isn't? I took Lucy's hand and led her out on the floor.