I Was A Serial Cheater

I Was A Serial Cheater

How and why I cheated on every relationship I had



I’m not proud of it. But I suppose it happens to the best of us. I had my reasons—which you’ll likely figure out for yourself after reading my story—but hey, cheating is cheating, and it’s wrong from all angles.


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First time.

I was a college sophomore and in my first real relationship. We had been together for about two years; she was six years my senior and just started life over. She had come home from the States and finally decided to go to law school. I wouldn’t call it love at first sight as the connection wasn’t instant but she’s smart and experienced; she showed me things I never even knew I wanted (see An Education). It could've been the age gap that made our relationship intense (she thought I was exciting), which I thought was good until we started fighting about everything.


I needed to escape, “it’s not working out,” I said. But every time we talked about taking breaks or just ending the relationship, she’d tell me “I’ll kill myself.” So, like any guilt-ridden coward, I stayed.


“I was in it for the thrill, for the sex, for the distraction…”


Then one day, during my internship, I met a guy. He was my age. He was overconfident and reckless. Me? Just the same. We wound up “friends” and later friends with benefits. I was in it for the thrill, for the sex, for the distraction and then things got too real. I started to care. Suddenly, I had two relationships to maintain; I had to see her and then him, and go back home to her.


Eventually he had to leave and a few months later, I fell in love with another girl. My girlfriend? I finally broke up with her. Worst few months of my life post that breakup: the gossip, the angry texts and the very real threats that ensued. Hell hath no fury like a woman scorned indeed.



At age 22, I was engaged to someone whom I knew was not the love of my life. But she took good care of me and treated me well, and I was—or so I thought I was—ready to settle down. Less than a year into the engagement, she and I suffered a loss that changed us both. For the worst at the start perhaps; I got angry and sought hard to feel something, anything, that I slept with an ex. Meanwhile, she sought comfort elsewhere. She never found out I cheated but I knew she did. The evidence, the pictures came to me. I didn’t even have to ask.


Christmastime, she told me she was leaving for the States but wasn’t sure when she was coming back.

We haven’t talked or seen each other since; it was as if the relationship never happened.


“I got angry and sought hard to feel something, anything, that I slept with an ex.”


Three’s a crowd.

But five is a company.


My girlfriend and I had been living together for a little over two years and short to say, our relationship looked pretty on the outside but it was so broken on the inside.

We met on a blind date—pre-Tinder years obviously—and it was fireworks. She was exactly my type; intelligent, well-spoken, a worldly woman. We hit it off almost immediately, had sex on our second date and lived together just a couple of weeks into dating. But things started to fall apart just as fast; she was domineering and disliked the idea of being “controlled.” My girlfriend had quite a temper, too, and to be honest a little too sheltered for my taste.


But I wasn’t perfect either; I was what you’d call the martyr in the relationship and I mean that in a pitiful and unattractive way; because when has it ever been attractive anyway? Eventually, however, she mellowed out while my self-esteem swelled (thanks to a pretty successful career).

But despite our efforts, the real problem never went away. Our values were just too different and the relationship came to a point where it felt like we were just friends shacking up and having occasional sex. But as “adults” do, we talked about parting ways. Having lived together for a while though, it was harder (more like inconvenient) to pack up years of our lives in rather small suitcases.


Our relationship had already been over before it was over. I could’ve manned up and left but instead I slept around—once with her friend, quite a few times with a common friend and had one full blown (mostly physical) but short-lived affair with an acquaintance. It broke her heart, especially after she’d seen pictures.


“I felt more relieved than I was sorry…”


And just like that, it was over. I felt more relieved than I was sorry, which tells you a lot about how terrible I was in relationships.



Today, I’ve been in the same relationship for five years with three kids to boot. Not once have I cheated. Chock it up to age, maturity or having kids but I’ve changed for the better. I realized the problem was not with the people I’ve dated, but with me; I was the problem.


There was always a choice to either stay and work things out or leave. If I left my first girlfriend, would she really have killed herself? Maybe not. She seems better than that anyway. But leaving means hurting the other person and being alone, too? Yes, it does. But it would’ve hurt less if I just ended the relationship instead of letting it drag on while I fucked around because “I wanted to feel something.” I was selfish and if I’m being honest, scared to be alone because I’m used to having someone around. Do I have regrets? None. But I am sorry. Sorry for causing unnecessary heartache.


“Do I have regrets? None. But I am sorry.”


So to you, if you ever find yourself in a relationship you know deep down is no longer working out or is going nowhere, be honest and rip off that bandaid. It’s less painful, I promise.



Art Alexandra Lara

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