There’s Good Cheating and Bad Cheating — Here’s How to Tell the Difference

To all you finger waggers: Not all the users of Ashley Madison are necessarily liars, and "cheating" can be more ethical than monogamy.


There’s been a lot of gleeful moralizing surrounding the Ashley Madison hack. I assume those who are gloating have never cheated on a lover, never struggled with temptations. If so, good for them. I suppose they’re entitled to a little schadenfreude. But given the puritanical, absolutist thinking (people who are on the website = bad. People who aren’t = good), I’m not sure they understand how websites like Ashley Madison are used. They may not, in fact, understand subtleties around sexual desire and romantic love. Relationships are complex. Monogamy is hard. There are many reasons people choose to have sex outside of their primary relationship, and they’re not all bad. In fact, I’d venture to say there’s good cheating and bad cheating, and it’s fairly easy to tell the difference. How do I know? Well, I’ve done both. So let me break it down.

Good Cheating

It was probably our third date when an ex-boyfriend I’ll call Jeff pulled out the book “Against Love: A Polemic” by Laura Kipnis, and read it out loud. Monogamy was unrealistic; domestic relationships were torture; infidelity was inevitable. Much to his surprise, I agreed. “I’ve never been great at monogamy,” I told him. Jeff was relieved. As our relationship progressed, we talked more and more about the possibility of a romantic partnership that would be committed and enduring but also admit for certain realities, like the fact that we would inevitably be attracted to other people. When we moved in together, we decided to have an open relationship with certain ground rules:

  • No sex with co-workers.
  • No sex with people we’d see regularly in a way that could make our lives inconvenient or uncomfortable.
  • No unprotected sex.
  • Total honesty.

That last one was key: We would tell each other everything — before and after the fact. And we’d tell the people we were with about our primary relationship, so everything would be above board from the start. The most important rule was this one: Our relationship was the priority. Having fun with other people was all well and good, but only if it didn’t compromise the integrity of our partnership.

And it worked. He was more permissive than I was, giving the go-ahead to my liaison with a female co-worker, even as it dragged on for almost a year and became emotionally complex. I preferred he stick to out-of-town trysts, though at one point he had a few dates with someone in town, and that was fine. This isn’t to say neither of us got jealous, but it made more sense to me than what I saw in the relationships around me: a mongamous commitment that would be irretrievably broken when one person cheated and the other found out. This was sometimes preceded by months of worrying: Why was she always working late? Wasn’t he more distant these days? Both partners would suffer with secret torment — whether guilt or suspicion — for months. Finally, along with the painful revelation of the truth, there was the agony of knowing that months of lies had come before, raising the question of what wasn’t a lie. How do you regain trust after that moment? To my mind, it was much easier to be honest. I used to laugh at the headlines I saw on magazine covers: “How to Tell If He’s Cheating!” In my case, I knew he was, and I knew exactly how it would go down. It made me feel safe.

The funny thing is that, in reality, Jeff and I mostly stayed at home, made dinner, and binge-watched The Wire. We hardly took advantage of our libertine arrangement. But knowing that we could, if we wanted to, took away the lure of the forbidden. Sometimes one of us would urge the other to take an opportunity. The most likely response? “Eh. I don’t know. I’d rather take the dog to the Shore this weekend. I can think about it later.” Most of the time, that later never came.

When our relationship ended, we both worried that we’d never find anyone else who’d share our philosophy of non-monogamy. But it has become increasingly common for people to design their relationships as we did — and to feel comfortable talking about it. In fact, there’s now a dating site called Open Minded specifically for people who are “open-minded about open relationships and non-monogamy.” The website’s founder, Brandon Wade, published a message on the site in March:

The new faces of the “open relationship” lifestyle aren’t porn hungry freaks or long-haired hippies, but rather successful, sophisticated, young professionals who do not view monogamy as an ideal. These individuals openly acknowledge that long-standing relationship may not meet each partner’s emotional or sexual needs all the time, and there is a need for a better alternative.

Wade also believes these kinds of partnerships are the “trend of where romantic relationships are headed in the future…” He calls it “ethical cheating,” but of course, it isn’t really cheating — that is, other people call it cheating, but the two people in the relationship probably put it less pejoratively: They might say they’re “monogamish,” as Dan Savage does, call themselves polyamorous, or do what I did and talk in terms of an open relationship.

Before Open Minded went online this year, people in open relationships used other sites to explore their options. Sites like Adult FriendFinder, Seeking Arrangement and, of course, Ashley Madison. Many of the people on Ashley Madison, it turns out, were not in monogamous relationships. Some were single, some were polyamorous, some had specific arrangements with their spouses. Some were dealing with desires that were unacceptable in their marriage but could be worked out with someone else — without breaking up a family. That can be ethical cheating, too.

Bad Cheating

All this is not to say that everyone on Ashley Madison was an honest broker. Surely plenty of people there were cheating unethically. I’ve done that too. In fact, the reason I got interested in open relationships to begin with is because I saw, from experience, the damage that a hidden desire for someone else could do. In those cases, I’d become so obsessed with the temptation, and the fact that I couldn’t act on it, that I’d start to pick fights, and resent things that never bothered me, so I could justify my own inevitable terrible behavior. And yes, it was inevitable: Knowing that it wasn’t allowed just made it seem more urgent. I used to think, “I’m my own person and this is my body and no one can tell me what to do with it.” I’d become a rebel in a haze of stupidity and hormones, and everything would be ruined. Even if my partner never found out, it would be too late for us to recover. I wouldn’t be able to find my way back.

Now that I’m in my 40s, I know that no one sexual encounter — or brief affair — is that important. It’s not going to alter the shape of my life in any significant way, so hurting another person, or jeopardizing my own peace of mind, is foolish. After a while, so many of the sexual moments and the people you had them with blend together. Is it worth damaging what you hold dear for something that becomes a dim memory? For the most part, you’ll remember the pain you inflicted with your cheating more than the actual cheating itself. And cheating is a mess, let me tell you. And it’s enervating. I wish we could all just read books instead. Think of how smart we’d be!

Today, entering into a monogamous commitment with someone is not just a pledge to keep it in your pants, so to speak. It’s also a way of saying, “Yeah, yeah, I know all about the divorce rate and high rate of infidelity, but I’m doing this anyway.” It’s a vow of sincerity in a cynical world. Cheating in that context? That’s awful.

Humans are living longer than ever, making the notion of a traditional lifelong partnership even more elusive. We see more serial monogamy now, less traditional marriage, more divorce. Secrets are harder to keep — too many sleepy people leaving their browser windows open when they stumble off to bed, or texting the wrong person by mistake. Monogamy is hard, but so is infidelity. Ethical cheating, it seems to me, is the easiest road.

So all those wagging their fingers at Ashley Madison subscribers might want to rethink their condemnation. Relationships are a lot more interesting than these modern-day puritans seem to know. Ashley Madison was just one tool among many. It’s 2015: time to understand that there are endless permutations of romantic love.

Follow @lspikol on Twitter.