How to Cheat: A Beginner’s Guide - OZY | A Modern Media Company

How to Cheat: A Beginner’s Guide

How to Cheat: A Beginner’s Guide

By Eugene S. Robinson


Because the more you know about sex, the better your sex will be.

By Eugene S. Robinson

Beating Cheating?

EUGENE, SIR: I’ve been married for 20 years but have recently fallen for a guy at work. He’s a former soldier. He’s built and has tattoos and the dirtiest mouth you’ve ever heard. I’m totally drawn to him, and I find an excuse every day to talk to him alone so I can hear his outrageous comments. My husband is a lovely gentleman whom I love and care for, but my co-worker is on my mind even when I’m at home. I’m not really asking for relationship advice, but rather how do I make a move without being accused of sexual harassment? And how do I not get caught? The other thing is, my co-worker is happily married and seems to be the loyal type, but the things he says are very suggestive. What would you do? — Irish Teacher XXX

Dear Éirinn Go Brách: Well, you’ve asked two questions. The latter one is easy to answer: I’d stay in my lane and wait for the crush to run its course absent any attempt to turn a harmless fantasy into a possibly harmful reality. Unless you have grounds to stray — your partner cheats, beats or has stopped having sex with you — any straying you do must then be understood as what it is: You wanting your cake and consuming it too.

Nothing wrong with that necessarily. It falls under the purview of what people do, and you’re a person, but I sort of had to say that so I’m not enabling the absolutely worst aspects of human behavior, mostly and specifically: inconsistency.

In any case, the earlier question I can sink my teeth into. I think most people having affairs buckle under the guilt and force a situation where they’re discovered, ending the affair and a goodly portion of their lives connected to the relationship they’d been stepping out on. Those who are really just there because they’re responding to an irresistible attraction (like you, it seems) either discover it’s so good that they feel guilty (and: see above) or so good that they feel bad and want to leave their primary relationship. Which, of course, will force your partner in crime to either join you or back out and leave you. 


The best that could be hoped for in the scenario you’re imagining, though, is two people coming together, having a great time for as long as a great time can be had and then parting when all of the signs are there that they should. It gets more complicated if there are kids, friends and family involved. Also, no one who has an affair at work ever manages to keep it secret. Discretion is not our lot in life it seems. So proceeding with caution is correct.

But you ask directly about the mechanics, which is to say, you’re asking me to help you commit a “crime.” I do not judge unless asked to, so I’ll say that the Hollywood way is too cute by way more than half a measure. Just keep it simple. Like Rain Man simple — “It’d be cool to chat outside of work some time” — and if he but blench, to twist Hamlet to our own uses, then you know your course. The B-portion of your query about not getting caught? That’s much more involved. Technology gets people caught on the regular. So does any kind of documentation. Acting like you’re in love might do it as well if your partner is perceptive. And venereal disease, that does it too. 

So the ways to get caught are legion. The ways to not get caught? Unsold and untold since we mostly hear about the failures. With the successes it’s largely impossible to distinguish dreamboat partners from excellent liars. Hope this makes some sense. Keep us posted and good luck. You’ll need it.

Hair Today, Here Tomorrow

EUGENE, SIR: I am being told that hair is in because it’s in magazines and “everybody is doing it,” and my girlfriend finds it kind of sexy. I told her if I wanted to have sex with someone who was hairy like a dude, I’d just have sex with a dude. She’s angry, and now I feel like an ass, but do I have to lie and say I like it because it was in some fucking fashion mag? Do you like it? — Bugged

Dear Bugged Bunny: This is less about me and more about you, so whether I like it or not is less important than where you find yourself now. For the record, though, having come of age in the ’70s, I prefer less hair on both men and women, and I find shaving relaxing and meditative. But to your question, no, you don’t have to lie. A little tact might have helped, but there’s a difference between lying and being tactful, as you may be learning now. This might help, though: Fully embrace people being and doing whatever they want, just as readily as you should embrace not being in a place that makes you unhappy. So, if hair is a deal breaker, let it break the deal and be done with it. If it’s not, then … tact.

Mouth vs. Face

EUGENE, SIR: My boyfriend likes to come on me, which is fine. He’s a good lover, and I’m often fully satisfied when he does. Last week, though, he came on my face and some got in my mouth. Again, this is fine, but when I went to kiss him after, he pulled back. I’m as disgusted with him as he apparently is with me. We’re six months in, so should I keep him or toss him? — Olive

Dear Ms. Oyl: Good lovers are hard to find, but stupid lovers are, at least based on the “Sex With Eugene” mailbag, a dime a dozen: Toss! 

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