Avoiding Failure in Adultery

By learning from others.

What was I getting into? I needed to figure it out. I’d mostly decided to have an affair, but something was holding me back. I’d been in a sexless marriage for ten years, and I was dying inside. It took a while to come around to the idea, and as I did, I read everything I found on cheaters and cheating. It sounds funny now, but I had no idea what to do or where to start.

Before I’d decided to cheat, I thought if I met someone for dinner, I might not need sex. I wondered if a little flirting could bring that feeling back. Late that summer, I signed up for Tinder and began looking for a date. I travelled for work so looked up people in the cities I went to, but it didn’t work out. I passed on many for one reason or another, chatted with a few, but never met anyone.

I read a lot of profiles, though. Everyone talked about kayaking, the outdoors and all those other things I would never do with them. They were looking for ‘the one.’ I was looking for ‘another one.’ I was looking for a romantic no sex dinner date. I was looking to dip my toe in the water without getting wet. I never did figure out how to make, “I want you to tell me what I want to hear, but won’t give anything in return,” sound appealing.

I worked to get my wedding rings off; they’d shrunk a little in the twenty-five years I’d worn them. I resized them to be single at will. Looking back, I was confused.

It struck me one morning that Tinder was going to be a disaster. How could I convince a guy to go out with me, pretend I was single, but also not want a relationship or sex? Who grows up dreaming of that? How would I explain not taking his calls — ever? I wanted to be a non-girlfriend girlfriend. It was absurd. I could lie to my husband, but how would I juggle lying to both? I deleted my account.

There had to be another way; there was if I could admit it to myself. I had the relationship without sex, so how would another help? What I needed was sex without a relationship because that’s what was missing. I had all the relationship I needed.

I signed up for Ashley Madison, the Tinder for married people, and started working on my profile. The idea of juggling lies made me think more about cheating’s perils, so as I filled out my profile, I wondered how cheaters got caught.

In turning to AM (as we call it), I realized learning how not to get caught was the most critical thing I needed to learn. Luck factored into it, but I was sure I could learn to cheat. Luck in my experience was a by-product of preparation and not a substitute for it.

Looking at failed affairs helped me map out how they failed. Knowing what they did wrong helped me focus on getting it right without blowing up my life. Cheaters call getting caught that. Failure wasn’t an option, so I dug deeper into my research, which revealed a complexity I’d underestimated. There were obvious things to avoid, but I was surprised by how many ‘points of failure’ there were.

Hair raising things like this — Hubby asks — ‘Hun, why did hotel X send you a thank you card for staying with them last month?” As your mouth dries, you’ll have two seconds to think. You’ll lose the first one figuring out what just happened and the next thinking of an answer. An answer that sounds less like, ‘I met a man for sex’ and more like, ‘not sure, but I made reservations their last month for dinner with the girls. Maybe it had something to do with that?

I’ve made enough mistakes enough to know it’s better not to. I also know it’s easier to lie when you expect you’ll have to. Studying failure exposed me to the lies I might later have to rely on and taught me what situations to avoid. Reddit helpfully opened my eyes. These stories stuck with me.

Redditor lnj5021[1]- My husband gave me an STD

My husband and I are high school sweethearts. He joined the military right after we graduated. This last year I noticed him being distant. I blamed it on …deployment. I’m sure I knew deep inside he was cheating, but I overlooked everything. I believed every lie he told me when he was out late, or never came home.

Two weeks ago I found out I had an STD. I finally have gotten him to admit he had multiple tinder accounts, and social dating sites. He has now admitted to have slept with three people, but has done stuff with many more.

Redditor Smart_Bum — My 5-year-old daughter told me

I was reading a bedtime story to my 5-year-old daughter, when she interrupts me in the middle of the story. She asks why mom was with another man and why were they on top of each other. I just paused and my heart just broke. The look in my daughter’s eyes assured me that she wasn’t lying.

From Redditor Gladdious — I accidentally picked up his phone

I sat down and picked up my phone. The text messages were already open but none of the conversations looked familiar. It dawned on me that I had picked up his phone by mistake (we had the same exact type of phone).

I found his texts. He had been wooing some girl and trying to talk her into moving in with him and offering to pay her truck payment (no idea how, since he couldn’t even make his own car payment). I was livid of course. I popped my card in his phone and copied the whole conversation, then transferred it to my phone for safekeeping in case he tried to delete it and deny it. I then texted the girl and asked her if she knew he had a girlfriend. Of course she didn’t. He had been playing both of us.

Redditor TwoToneSun — I tracked her on the ‘Find My Friends’ app

We were going through a rough patch that had lasted a couple of weeks. I was a bit suspicious and looked on the ‘Find My Friends’ app. She was located somewhere where I’d never heard her talk about. I left work early and drove there and waited. Two hours later, she and her boss walk out kissing and cuddling on the street. One phone call later to his wife, my ex gets sacked, the boss is divorced, and the company breaks up (it was husband/wife own and operated).

Redditor throwaway8675309 — I found nudes and chat logs on his old phone

I caught my husband cheating about a year ago, he had been texting with some girl and they were sending nudes to each other. I found out about the whole thing accidentally. Someone was interested in buying his old smartphone online, so when I turned on the phone to make sure there was no personal info in it, I found the pictures and chat logs.

Redditor Shruggalicious — I read his Facebook Messages

My friends were trying to warn me, but since it was only rumors I pretended everything was fine. I trusted him so much that I had his Facebook profile password but never disrespected his privacy. When the rumors started to bug me I logged into his Facebook profile and read the messages. Not only did I learn he was cheating on me, but found out he got another girl pregnant.

Some of these are awful, but instructive. The failures were a sobering reminder that cheating comes at a high cost, but I saw opportunity in them too. Cheating is not for everyone, and we all do so for our own reasons. I’m in no position to judge, but what I do know is if you understand the risk, it’s easier to avoid. Some people are better at thinking on their feet I suppose, but like most things, cheatology can be learned. And if you learn well, you might just make it.

I haven’t been caught…yet. And that’s about the all a cheater can say about that. My affair partner and I have been together for two years and are going strong.

Learn more by following my Series where I distill cheating into easy to read tips, or from my book on Amazon — How to Cheat: Field Notes from an Adulteress


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© Teresa J. Conway, 2020

By Teresa J Conway on .

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Exported from Medium on March 4, 2021.

Author of How to Cheat: Field Notes from an Adulteress, several short stories, I'm active on Medium @teresajconway where I sometimes share my blog posts, and I'm a fair-weather tweeter @tjconway69.

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