Feb. 2005 Esquire

Let's say you have two friends named Jack and Jane. They have been romantically involved for two years, and the relationship has always been good. Then one day Jack calls you and sadly mutters, "Jane just brok up with me. She thinks I cheated on her." You ask, "Well did you?" Jack says, "I'm not sure. Something strange happened." This is what Jack proceeds to tell you:
There is this woman in my apartment building who I barely know. I've seen her in the hallway a few times, and we've just sort of nodded our hellos. Last week I came home from the bar very drunk, and I ran into her while I was getting my mail. She was drunk, too. So just to be neighborly, we decided to go to her apartment to have one more beer. But because we were intoxicated, the conversation was very looes and slightly flirtatious. She suddenly tells me that she has a bizarre sexual quirk: she can have an orgasm only if a man watches her masturbate. This struck me as fascinating, so I started asking questions why this was. And then--somehow--it just sort of happened. I never touched her and I never kissed her, but I ended up watching this woman masturbate. And then I went home and went to bed. I told Jane about this a few days later, mostly because it was all so weird. But Jane went fucking insane, and she angrily said our relationship was over.

Whose side do you take, Jack's or Jane's?
(The author writes) I have posed this question to myriad people, and their reactions fall into two broad categories. Women almost always think Jane's rage is completely valid; men typically inquire about the availability of housing in Jack's hypothetical building. Women usually agree that this offense warrants a breakup, while most men think it merely deserves tenure in the doghouse. What's noteworthy is that no one disputes that Jack did something wrong, everyone uses a slighly different, weirdly personal argument to explain what makes it so bad.
The scenario raises so many other questions. How different is this from watching porn? How different is it from getting a lap dance? Is this situation better or worse than if Jack had drunkenly kissed his neighbor? Would it make any difference if the neighbor had been behind a glass partition? Many people point to the intimacy of the exchange. But if that's the case, the conversation preceding the episode seems as troublesome as the masturbation itself. And if Jack honestly saw this encounter as "weird" (as opposed to "erotic") shouldn't he be forgiven completely?
This is why the Jack and Jane Hypothetical is such a vexing scenario. The question really isn't "Whose side do you take?" The true question is "When, exactly, does cheating begin?"
(Author goes on to talk about how due to lifespan its mathematically unreasonable to be monogamous. How it's not about physical contact or emotional intimacy; it begins the moment anyone decides that it's unreasonable to be sexually committed to one person.)
But here is the bottom line: Motivation is everything. Wanting to cheat on someone but failing is no different from actually cheating, and the reason something happens is way more important than the action itself. "This is why watching your neighbor masturbate is not necessarily a reason to lose your girlfriend, particularly if you were drunk and merely trying to get your mail. And if you disagree with this, you're just being unreasonable"


If you want to see all the mumbo-jumbo about why monogamy is mathematically unreasonable pick up the February 2005 issue of Esquire and flip to pages 53-55.

New favorite quote for Andrew: "What you say doesn't matter as much as why you choose to say it"