Why I Cheated (From The 'Type Of Person' You Thought Would NEVER)

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Why I Cheated
Heartbreak, Love

People have all sorts of reasons for why they do what they do, without having it define them.

Around mile 75 of our 250 mile drive to Boston, my boyfriend of three months asked me if I had ever cheated on anyone. He had been in a brief relationship a few years earlier, which abruptly ended when he found out the woman he had been with had cheated.

"That's something I have zero tolerance for," he told me.

I nodded, said nothing, and tightened my hands on the steering wheel. I saw, out of the corner of my eye, him look at me. "Or," he faltered. "I don't know. Maybe you'll tell me you've done that and—"

We had, at the same time, both realized how much there still is to learn about a person after just three short months. And, what? I wanted to ask him. And maybe he would think differently of me? Maybe he would try to understand why?

My boyfriend thinks that I'm kind, smart, and, perhaps most important, honest. I knew in his mind that this equated to the "sort of person" who would never cheat. 

I allowed the question to hang between us. I wanted just a few more moments of thinking I was the person he believed me to be.

"Yes," I said finally, eyes fixed on the vast expanse of the open highway before us. "I've cheated."


Before meeting my current boyfriend, I had been in only one other serious relationship. It was a four-and-a-half-year, on and off, tumultuous relationship in which I was consistently verbally and emotionally abused — a realization I have only been able to come to in the aftermath.

I cheated on this man three separate times with three separate men. I did not sleep with these men. But I flirted with them and I kissed them.

The first time was with a man who I met through friends. He gave me consistent attention during the time when my boyfriend was still struggling with the "exclusivity" deal of our relationship.

"I'm just not ready for labels," my boyfriend would tell me. I was 22 and had just started working full-time in Manhattan. He was 23, on year five of completing his college degree. He wanted to have "fun" before graduating.

When my boyfriend finally was ready to be called "my boyfriend," I had just moved near New York City. He chose to tie me down the moment I was set free, after a year and a half of me asking him for a relationship. It had been what I wanted but I was exhausted by the struggle.

I didn't even know what "exclusive" meant for us; all I knew was the gray in between. Worse, my confidence was broken down. Why did it take so long for him to realize he wanted to be with only me?

One night at a local bar, the man I met through friends tried to kiss me. He had made it clear to me over the previous few months, before my boyfriend and I were official, that he was attracted to me.

"I thought you said you two weren't exclusive," he protested when I pushed him away.

"Well, we're together now," I said, half-heartedly.

"So, it took this guy over a year to figure out that he wanted to be with you," this man told me, leaning in. "Sounds like he's an idiot."

We kissed that night, and a few more times over the course of a few weeks. By then, my boyfriend was starting to become integrated into my group of friends. The two were going to end up meeting, and I started to worry about how messy the situation had become. I had gotten used to being a "girlfriend," and understood now that what I was doing was wrong.


The second time I cheated happened over a year later. My boyfriend had just gotten back from a work trip in Las Vegas and, jokingly, I asked if he had kissed another girl. It was about the biggest cliché I could think of, and in the ensuing silence, I froze.

"Did you?" I asked in horror.

"She kissed me," he said, hands in the air. I started to cry and he immediately rolled his eyes. "I knew you would do this," he hissed. "I knew you'd immediately blame me." He urged me to calm down. "Relax," he muttered, looking around. "People are going to stare."

Two weeks later, I took a trip to Georgia to visit a friend. There, I met the charming, handsome friend of her ex-boyfriend. He and I chatted throughout the night, bar-hopping and exploring the town. When he kissed me, I kissed him back.

I told my boyfriend soon after and he shouted at me that I was seeking revenge on him. I knew he was right. We fought for hours until he ultimately forgave me, and we never talked about it again.

Almost three months later, my best friend was in town, and my boyfriend would have been arriving at my apartment any minute for a fun night out. His name flashed up on my phone. I answered giddily, wine glass in my hand, waving to my friends with the other as I closed the door to my room to better hear him.

"Are you looking for parking?"

"No," he said. His voice was cold. "Listen, I'm not coming."

My heart sank fast; I felt tears spring to my eyes, a knot form in my stomach.


"What? But, I told everyone you were — you said—" My vision blurred. I sat on my bed. I quoted back to him when he had confirmed he was coming. I had checked, and double checked. He had promised he wouldn't let me down, again. I reminded him of this, too.

"Don't quote me," he said, voice rising. "Things come up. I'm tired."

"But you said" I began desperately. It was one of dozens of times that he blew me off at the last minute  for being tired, for his friends, for no reason at all.

"I told you not to f*cking quote me! If you don't shut up, I'm going to come there and slap your face shut," he shouted at me. I hung up in a fury. I did not know then that I would kiss another man at the bar that night.

"I still have a boyfriend," I drunkenly confessed to this man, a man I knew, who had always been kind to me. "But he's treating me terribly."

The following morning, in my friend's car, I sat with my head pressed against the cool glass of her window. "I mean," she justified. "It was just a friendly kiss, wasn't it?"

I never told my boyfriend, not then and not when we broke up months later.

In the aftermath of the relationship, I had a hard time learning to trust, even though I knew that on paper I had been the more mistrustful one. It took me years to recognize my boyfriend's behavior as verbally abusive and manipulative.

"Good luck finding anyone else," he told me once, during yet another fight where I expressed being fed up with the way he treated me. "No one will ever love you." When, later, I told him how much his words had hurt me, he told me he had no recollection of saying them. I must have misheard, as I often did, according to him.


At the time, I couldn't figure out why I kept cheating. I must have needed the attention, I thought miserably (certainly my boyfriend often told me I required too much). But in a way, this was true. The men I cheated with told me I was beautiful when my boyfriend never did. They wanted to kiss me when my boyfriend pointed out to me that I wasn't a very good kisser.

I cheated because I had been so broken down that I thought I couldn't leave. I was made to believe I was so un-pretty, un-kissable, unlovable, that no one else would ever want to be with me. The men I cheated with made me feel more desired in one night than I had felt in four years with this man. It was the only way I felt like I could maintain a semblance of control in a situation that had spun so far out of hand.

When it ended, it wasn't monumental or scandalous. He had blown off yet another date in favor of drinking with friends and then grew angry when I became upset. Finally, inexplicably, I had had enough, and told him so. He texted me later that night: "I'm sorry you don't understand me."

I'm not excusing cheating or attempting to justify my own. Had I been the sort of person who could recognize her own self-worth, I would have left my ex-boyfriend long before that first unfaithful kiss. When I did leave, I vowed I would never stand for the sort of abusive behavior that I put up with in that relationship. I swore I would never date someone who would bring out the vindictive side of me, the side that had a propensity to cheat out of revenge and insecurity.

What I learned between my past relationship and my current one is that there are no absolutes. There is no "sort of person." People have all sorts of reasons for why they do what they do, without having it define them.

Sometimes, all it takes is one person to bring out the worst — or best — possible version of yourself. And sometimes, it's only after being both that you can then choose who you want to be.

When I'm with my current boyfriend, I'm the person my ex-boyfriend had so determinedly stifled. He builds me up rather than breaks me down.


By the end of that drive to Boston, my boyfriend had listened to my side of the story. He decided to pass judgment based on the person he knows now, not the person I was then. And he continues to think — despite all of this — that I'm kind, smart, and honest.

He tells me this so assuredly that I have no choice but to believe him.


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