3 Hard Lessons I've Learned By Cheating 6 Times

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I’m not proud of what I’ve done, of the pain and hurt I’ve caused.

By Liz Lazzara

I never thought that I would be the sort of girl who would take part in infidelity, but I have cheated six times.

Before the first time, I told myself that if I got to the point where I wanted to step out on my partner, I would end the relationship before I crossed the line. I told myself that the emotional damage that I would inflict on my partner would far surpass any thrill. I told myself I would feel immeasurable guilt. I told myself that if someone was willing to cheat with me, they’d soon cheat on me.

In many ways, I was right. But in so many others, I was wrong.

I’m not proud of what I’ve done, of the pain and hurt I’ve caused. But I have come to the realization that each instance of infidelity imparted a lesson I needed to learn: to find a better partner, to come to grips with my fears, and to be a better person.

1. Don’t stay with someone who doesn’t value you sexually.

The first time I cheated, I eased into it, like dipping a toe into forbidden water.

I began by talking to a male friend, Alex*, about the lack of sexual intimacy in my relationship. I thought telling him would be akin to venting to my girlfriends. For a long time, it was. We would chat on AIM, and I would feel heard, even as my boyfriend Charles* played video games with his roommates mere feet from me.

However, one day, I hit a breaking point. I was sick of spending time at my boyfriend’s on-campus apartment when I had an empty one of my own five minutes away. I was tired of masturbating after class and before his roommate got home to take the edge off my sex drive.

I wanted to be wanted, and even though Charles and I had set a wedding date and put two and a half years into our relationship, I was sick of talking about my libido like another couple would talk about whose turn it was to load the dishwasher.

I wanted to blow off some steam, so I changed into workout clothes, intent on going for a run. Alex offered to go with me, and I thought nothing of it. We had broached the subject of my sex life before with no blowback, and I didn’t anticipate any then.

But when I stripped naked in Charles’ room and saw that he wouldn’t even look up from what he was doing to admire my body, something snapped.

That night, I didn’t cheat physically, but I certainly cheated emotionally. I spent hours with Alex, talking through my troubles; and then, when he invited me back to his dorm, I said, “Yes.” I didn’t intend to flirt, but when it became clear that there were sparks between us, I devoured them hungrily.

We never kissed and barely touched, but I realized then that I was sexually starving.

I went home late that night and told Charles we needed a break, during which I dedicated myself to pleasing Alex. His every admiration gave me the validation I needed — the belief that I wasn’t ugly, or un-sexy, or unworthy.

If someone I had known for a matter of months could give me that, why couldn’t my boyfriend of years?

I left Charles with that question in mind, knowing I would never abide by being taken for granted again.

My future relationships would be filled with passion between the sheets, come hell or high water; and if I hadn’t stepped outside the lines with Alex, I don’t believe I ever would have come to that determination.

2. Don’t stay with someone who’s emotionally abusive.

The second time I cheated, it was completely deliberate, almost a game. At the time, I was with Michael*, a gregarious guy who was once my best friend, but became my lover.

When we were out in public, we looked like the perfect couple — partners in crime, sexually connected, everything a relationship ought to be.

At home, though, things were different.

He gave me the sexual satisfaction that I’d lacked with Charles; but if I ever tried to have a serious conversation, he’d turn cold and distant, going so far as to threaten to leave me.

Sometimes he’d follow through, and I’d beg and plead my way back into commitment, remembering the promises we’d made to each other to never give up on what we had, and believing to my core that no one would ever love me like he did.

Then, on a trip to my home-state, I met Arthur*, an artist and friend-of-a-friend who immediately intrigued me. I loved poring over his sketchbooks and talking with him about his artistic goals.

One night, we went underwear-swimming in a local lake. When I jumped off the dock, my front-clasping bra broke and I couldn’t wear my white t-shirt for fear of flashing everyone. Arthur gave me some clothes to wear home, and his smell was intoxicating.

I wanted him to notice me.

On the night of my birthday celebration, I took the opportunity to kiss him in the tent I’d erected in the yard to keep people from driving home drunk. I thought I was simply rebelling against Michael, but instead, something else happened: For the night, Arthur became a sort-of boyfriend.

We held hands on a late night walk to Dunkin Donuts, and he offered me his shoes since I’d made the ridiculous decision to go barefoot. He gave me a piggy-back ride through the streets, and cuddled me in the tent that night between many, many more kisses.

Sometime between midnight and dawn, I asked him about the tattoo on his collarbone. It was dedicated to his deceased father, he answered.

I felt intimacy, if only for a night.

I confessed to Michael the next day and he told me he wanted to carry on with our relationship. I was shocked, convinced that my indiscretion was unforgivable.

In the end, it didn’t matter. I broke up with Michael within a matter of days.

Once I had gotten the taste of respect, decency, and sweetness, I couldn’t ride his manipulative rollercoaster anymore. I thank Arthur for teaching me that lesson, even though I never saw him again. Without him, I could very well be imprisoned in that relationship still, believing that I never deserved better than what meager scraps of love I was given.

3. Don’t be afraid to break the rules.

The third time I cheated, I wasn’t with anyone at all — I was the “other woman.” The man— Cal* — was my internship supervisor.

He was 11 years older, and he’d been dating a woman for five years: someone he lived with, and someone I respected very much.

Everything I believed in told me not to pursue this man. You’re not supposed to get involved with someone at work. You’re not supposed to date someone much older. You’re not supposed to cheat with someone because later, they’ll only cheat on you.

But I couldn’t help myself — I was smitten.

I started to become jealous every time his girlfriend would come to whisk him away from the conversations we were having about books, movies, and television. One night, we went out with a friend of mine and two other coworkers — I drank and danced with Cal. He picked me up and swung me around like I was his lover.

Then, the night before Valentine’s Day, after seven hours of shared appetizers, cigarettes, and illicit stories, he kissed me in the parking lot of the bar, and something inside me came abruptly and powerfully alive.

We slept together a week later, and spent every night we could in my apartment, drinking expensive scotch on the rocks and putting out cigarette butts in the watery remnants. We’d listen to Tom Waits, Nick Drake, and Nick Cave and I’d lie with my head in his lap, twitterpated to the brim of my existence.

There were rules, of course, but we broke them all.

We promised not to fall in love, but a month in, he all but begged me to say it first.

We promised that our affair would end in June, but it continued well into the summer.

Most of all, we promised that his girlfriend would never get hurt, but when he told me I was The One, we both knew that relationship had to end so ours could really begin.

Two years later we were married, something I never expected. If I had followed my head instead of my heart, I would have missed out on the opportunity to know the nature of true love.

We have been separated for six months, though we still talk often. Sometimes we rehash our hurts. Other times we share our perhaps ill-conceived hopes.

Many times we talk like we used to: about art, work, our cats, and private jokes. I don’t know what the future holds for us, but I can say that I wouldn’t give up our three years together for anything. Without risking the stigma and potential pain of being someone’s mistress, those three years would never have been mine, proving to me that sometimes, if rarely, cheating can lead to something beautiful and true.

I can’t say for certain which of my decisions were right and which have been wrong. Cheating opened my eyes to relationships I needed to leave. It gave me the first healthy relationship I ever had. It hurt the men I loved and an innocent woman who did nothing to deserve it. Can I really defend my infidelities in that light?

But what I can say is that, in spite of the mistakes, pain, guilt, and uncertainty, I learned what I want from a relationship.

I learned what not to accept from the men who claim to love me. I learned that in matters of the heart, there are no hard and fast rules. An integral part of who I am has been built on the crumbling bricks of infidelity; and, for better or worse, I’ll take that person and love her with all my heart.

*Names have been changed

This article was originally published at Ravishly. Reprinted with permission from the author.


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