Confessions of a Former Cheater
Is it possible to go from cheating to successful non-monogamy? I could be biased, but I say yes.
Listen to me read this story with my weird sick voice:
This story contains sexual content and material that may not be suitable for younger readers. Reader discretion is advised.
~
The first time I cheated on someone I was 16 years old.
It was summer. It was on the beach somewhere on the coast of Nova Scotia, fueled by vodka, nostalgia, and teenage lust.
I was wearing my red Paul Frank hoodie with the monkey emblazoned across the chest and blue terrycloth low-rise lounge pants that were the bottom half of a matching set à la Juicy Couture except mine were probably American Eagle.
He was wearing a green hoodie and dark sweatpants — there was a fire going, people were everywhere, it was a brisk night for August.
He was my fifth-grade boyfriend, the one whose name I doodled across notebooks, diaries, and the back of my hand inside a heart. The one I slow danced with to “My Heart Will Go On” in someone’s living room at a boy-girl party while everyone else watched. We’d kissed once or twice as preteens (barely), but moving away when I was twelve seriously messed with my game. We’d come together that summer with a bunch of friends at a cottage and when we arrived he claimed the top bunk for me and him.
My heart raced. He wanted to share a cozy bunk with me?
Earlier that year I’d had sex with a boy for the first time, with my high school boyfriend who was a year older than me, who I’d met when we were both involved with a play at his school. My all-girls, private Catholic school, and his all-boys equivalent would often mine each other’s hallways for talent when gendered theatre or events required it.
We’d said “I love you” and meant it, as much as one can mean it when you’re a teen and on the hormonal precipice of having sex. Sometimes I think we mean it even more then, when we’re young and unencumbered by life’s vast experience that makes us jaded, hopeful, comfortable, and uncomfortable all at once. We’re able to feel it with everything we have because life hasn’t hardened us or taken up space yet; we have so much capacity for love. I wrote poems about how fiercely I loved him that live in sketchbooks that are lost to a family purge somewhere along the line.
So when the vodka, nostalgia and teenage lust took over I found myself fumbling around on the beach (sand everywhere!), under the stars, doing it. Having sex. With someone who wasn’t my boyfriend.
Returning home I was wrecked with guilt. He was so good to me and we were really happy! But I confessed my dirty secret in the parking lot of the zoo when we reconnected to talk about my trip. He wanted to make out in his car like we always did (so did I!) but instead of kisses it was my illicit encounter that spilled from my lips and I burst into tears.
I felt terrible.
I was honest, and I told him that I should probably be on my own to figure out what I actually wanted, and I felt so much shame for what I’d done to him.
So we broke up and eventually many years later reconnected as adults and as friends who could finally laugh about a pretty awful situation.
Whether or not that experience shaped the rest of my relationship life is hard to say, but it certainly set a tone. My second high school boyfriend cheated on me, likely more than once, which I took as karma for what I’d done.
At 19 I started working in restaurants, and that is one atmosphere where age becomes but a number if you were old enough to serve and drink alcohol.
After I slept with my first general manager (a strict workplace no-no), I started dating a foul-mouthed, dirty-sexy line cook who was six years older than me, smoked cigarettes, and said things like “hey gorgeous,” to all the servers, and loved to eat pussy.
We had a great time together, smoking weed, fucking, and watching porn from a VHS in his bedroom. We’d send each other sexy photos on our not-so-smart phones until I realized I wasn’t the only one he was exchanging sexy photos with. We’d never discussed what qualified as cheating in our relationship, so of course, we disagreed on the subject, the trust was broken, and we tried to move forward gracefully.
I don’t know if it was that, or the fact that he went away for four months and we tried to do long distance, or that I caught the attention of a manager at my new restaurant (I know, I know) — but the itch came, and goddamn I love to scratch.
While my partner was away I started spending more time with my new coworkers, drinking until after hours and hanging out at each other’s apartments. At some point, my manager started texting me increasingly inappropriate messages which of course I loved. There was something taboo about it, something exciting about catching the eye of another older authority figure, who also happened to be a close friend of my boyfriend’s.
I don’t remember how it started, but it was inevitable that those sexy texts were going to morph into something physical. I’d start switching shifts to close when he was closing so he’d offer me a ride home in his two-door black Sunfire, but really we’d go to his place and do bottle tokes and dance to power ballads and fuck on his period-stained mattress on the floor because he didn’t have a bed frame. The stain, I learned, was a remnant of another server he’d bedded not long before.
I was twenty, and he was thirty.
I know now that the power dynamics (age, the fact that he was my boss) were incredibly skewed but at the time I thought I was just the *most* mature. I’d go to his place on a split shift if he wasn’t working and go back to work freshly fucked for the second half of my day.
I kept it a secret, until I didn’t. I confided in a select few who I trusted with the secret of my affair, one of whom thought it their duty to tell my boyfriend that I was fucking one of his best friends.
Having my shame aired out for all to hear was incredibly hard. My partner called me a lying slut and threatened to call my parents and tell them their kid’s a whore. He didn’t, thank god. I was embarrassed to go out in public in my small town for fear that everyone would somehow know what I did and shun me for it. I was afraid my parents would somehow hear about it so I confessed to my mother one day, who wasn’t exactly sure what to do with the information, and responded in the most Irish Catholic way possible: pretending it never happened.
I don’t know if I actually fell for him, or I just wanted to prove to everyone who was shocked by the revelation (aka our friends and coworkers) that it was for love, not lust. As if that made it better.
I maintained a relationship with him for four years, the first half of my twenties. We had our ups and downs, like everyone, but I knew it wasn’t forever. When I realized he was cheating on me consistently and indiscriminately via craigslist and kijiji personal ads, my world fell apart. I confronted him and had my first conversation about exploring an open relationship, suggesting that we could try new things together and it could be kinda fun. We never got that far. He refused to talk about it after that. It was, as they say, the beginning of the end.
Sure, we stayed together for far too long afterward because my heteronormative conditioning told me that relationships are hard and involve sacrifice and compromise and besides I couldn’t admit that the relationship was a failure after everything I’d done to wind up there.
On my twenty-fourth birthday he whispered “I’m gonna put a baby in you this year,” and for me, that was the middle of the end. Not because I was sure then that I didn’t want to have kids (I had an inkling) but because it was just another decision he made without consulting me first. The first was when he surprised me by moving to Halifax after I went there for university. We hadn’t talked about it, but for Christmas I was gifted a “Surprise! I’m moving!” coupon and I didn’t know enough about boundaries and what I wanted to admit that inside I was screaming NO.
I broke up with him later that year, in the week following my diagnosis of and first surgery for endometriosis. He said he’d just bought me an engagement ring, and I knew instantly I was doing the right thing. Before long he was engaged to someone he met while we were still sharing the same apartment. That was the end of the end.
~
The next time I was involved in a cheating triangle, it was as the mistress.
Another restaurant, another foul-mouthed line cook who smoked cigarettes, and bonus this one did cocaine too, something that was almost entirely new to me.
He’d moved to the east coast from Toronto with his girlfriend, who he never really had anything nice to say about — 🚩🚩🚩 — who I never met because she refused to come to the restaurant he worked at or meet his friends. The more I learned about their relationship the more I understood why she wouldn’t, but at the time I didn’t care. I was single, in my slut era, working hard, and partying my ass off. We were working constantly and needed to blow off lots of steam. I started meeting him at out-of-the-way spots so we could talk and drink and smoke and do key bumps in the bathroom, and eventually fuck. It felt good that he was confiding in me, that I was the one he wanted to know things no one else knew. It makes me cringe just thinking about it.
Sleeping together was inevitable. She traveled for work and we made good use of that time, fucking in their condo while their cat watched. It wasn’t his first rodeo, he liked to tell me 🚩🚩🚩 I hated myself for what I was doing, but managed to convince myself that I was an innocent party. One with zero attachments to any outcome.
She started to suspect something was up (ahem, see rodeo comment regarding his history of cheating) and one night started texting me from his phone, trying to get me to admit our dalliances. I didn’t, and they broke up. He moved in with me and my best friend and when I initially lied to her about sleeping with him I knew I was doing something really bad.
Once again I tried to prove that I wasn’t “just a slut,” but that it was for love. As if that excused my behaviour. Six months later I moved to Toronto because he wanted to go back home. We were together for six years. He got engaged to someone he met while I was still packing up his shit.
~
I’m not proud of my history on every side of the distorted cheating triangle. But I am proud that I’ve left those ways behind.
As a nonmonogamous person, you often hear the narrative that cheating is just a form of nonmonogamy.
This is so far from the truth.
Cheating is rooted in deception, secrets, and lies. It breaks a contract between people, thrives on dishonesty, and lives in the shadows.
A 2015 poll of nearly 2,500 married Canadians following notorious infidelity site Ashley Madison’s data breach from Mainstreet Research found that 10% of Canadians admitted to cheating on their partner. 80% said no, and 10% didn’t answer. More than double that and you’ve got the percentage of people who have admitted to thinking about cheating on their partner. The poll does point out that definitions of cheating are not consistent among relationships and (cis) genders.
The data breach released the information of over 32 million unfaithful partners using the service, but by the end of 2020 their membership surpassed 70 million, assisted by the COVID-19 pandemic.
Is it loneliness? Boredom? The desire for something new? An inability to communicate effectively with our partners? The conditioning of compulsory mongamy and heteronormativity that teaches us we have to find one person to be our Everything? The fact that cheating can be illicit and a bit of a thrill? Until it’s not. And it always. becomes. not.
Nonmonogamy isn’t cheating because it involves open, honest communication and checking in and having hard conversations and being humble and setting boundaries and coming up against them and learning how to adapt. Let’s be honest, monogamy should involve all of those things too but we’re taught that The One will just understand you, and jealousy and possessiveness is conditioned into the fabric of monogamy - “My beloved is mine and I am his.” Jealousy can be a real mother fucker until you learn to ask why it’s there. But that’s a story for another day.
~
I knew the first time I ate pussy in front of a boyfriend that I could never *truly* be monogamous, but that didn’t stop me from trying. The next few times it happened it started to hit me that maybe I didn’t want one person to be my Everything. That I didn’t want to be that for someone else. That I wanted a life full of friends that you fuck and that you love and that you date and that you learn about and evolve with and become something new with every day.
I know myself well enough now (even though I’m forever learning) to wish I could go back to my younger self on that beach somewhere on the coast of Nova Scotia, to that blood-stained mattress in the middle of the floor, to that condo couch, and tell them it’s okay.
That they don’t have to lie and cheat for the sake of monogamy.
That they’re not evil or bad or a terrible person for not wanting to be monogamous and never having the tools to express that’s what they wanted.
That sometimes it’s going to fucking suck and they’ll hurt people and make mistakes but they need all of it to learn about who they are and make more mistakes and be hurt and learn how to build the life they want.
That they’re doing their best, and will figure it out eventually.
No, I’m not proud to be a former cheater but I’m hella proud to be building a life full of relationships based on honesty and open communication. And a lot of laughter.