I’ve Cheated on Every Boyfriend
We were sitting close enough together on the edge of his bed that I could feel the heat of his body without actually touching him. A nervous magnetism was keeping us closer together than necessary, and also, just slightly apart. If energy in air were visible, the inches between our respective thighs would’ve been flashing neon.
The charge came from a tenuous, unspoken sexual attraction that was the entire basis of our “friendship”—one we’d never actually acknowledged because I was, at the time, in a serious relationship. My boyfriend—we’ll say his name is Matt*—was a mutual friend. I’d come to Drew’s* place that night in early summer under some ridiculous guise I can’t even remember now… but it had worked. So there we sat, thighs squishing against the sagging side of his bed, waiting for either something or nothing to happen.
Before you hate me for what comes next, you should know something: I hadn’t felt my body heat up like that in months. Matt and I had sex every day (sometimes multiple times a day) for the first two years of our relationship. But by that humid night in early June, we’d stopped—not entirely, but enough so that he could look at me before we fell asleep and tell me the exact number of days it’d been since we’d fucked.
I was 21. So, when I started feeling an aversion to having sex ( which l met on a dating site ) with my boyfriend, I thought: These are my horniest years, something must be wrong with me. I considered seeing a therapist to try and fix myself. It hadn’t yet occurred to me that maybe I didn’t want to have sex with my boyfriend because of who he was. The way he kept track of the days since we’d last had sex felt more like a threat than a concern.
And, at the time, I didn’t yet know the difference between loving someone and just needing to hold onto them. This is not an excuse to lie to someone you’ve said “I love you” to, but it’s what was flashing across the ticker tape of my brain in the moments before what happened next on Drew’s bed. Someone touched the other first, and then mouths were on each other, and hands were moving so fast they grabbed at clothes and skin with the same urgency.
We were horizontal—half-dressed and damp from the heat and our nerves—before my phone buzzed us back into reality. That was the first time I ever cheated on a boyfriend.
Cheating is one of the big Nos, a flashing DO NOT PASS sign, one of the few things most people in the world can agree is very bad. It’s a capital-S Scandal—something you have to have literally Beyoncé-level strength to forgive. And I would know: I saw one of my parents do it to the other, and now, because of that, they are no longer married.
Still, knowing this, I’ve cheated on all three of my serious boyfriends. I’m not completely morally bankrupt, and I feel bad for lying… even if the lie only lived for a few days or weeks until I broke up with each guy. But I don’t regret each instance of cheating. Not really. Because, though they were all very different, each experience taught me crucial things about myself and my sexuality in my early twenties.
The frenzied grabbing and kissing on Drew’s bed that night, for instance, didn’t immediately reveal to me how badly I needed to break up with Matt. But, it did show me that my sexuality hadn’t dried up, like I was worrying it had. I was still capable of feeling tingly and wild; and the urge to squeeze my body so close to someone else’s that the only logical answer is to be inside each other was still there. Over the coming weeks, I noticed how not-there that feeling was with Matt—how it had never really been there at all. It wasn’t me that was broken, it was our relationship. And I think it would’ve taken me so much longer to realize that if I’d just walked out of Drew’s room that night.
So, I don’t really think cheating is a capital offense. Not when you’re young and still trying to learn how your heart and body work. I think about the way my grandparents—who are in their eighties and still happily married—talk about their early relationships, and how much more laid back they were than any of mine. They talk about going on dates in groups of people, and attraction that felt like popcorn in a hot pan—quick and random. Things were casual and open until they were very serious. That’s not really how people date anymore. And so, instead, some people cheat.
The second time I cheated on a boyfriend was in the backyard of a crowded outdoor bar. Again, it was hot out, and the humidity felt like another person in the room. The guy I was dating (we’ll call him Adam*), wasn’t there, but a friend (who we’ll call Kyle*) was. After downing three plastic cups of sticky liquor mixed with stickier juice, I confided into Kyle’s chest that things with Adam weren’t working. I was in love with Adam, and wanted to be with him, but we weren’t having sex… and we hadn’t in a few months.
I’d tried talking to Adam about it, but he never wanted to, which made me feel bad. I loved so much about him that I convinced myself it was fine. I didn’t need to have sex with my boyfriend as much as I thought I did, I thought. Girls can do without. But that night at the bar, it became very clear I was lying to myself. After dancing with friends for a few hours, my skin felt lit up in all the places where anyone had touched it—like handprints left on clean, steamy glass. It was an undue amount of excitement for casual contact, and I needed more.
So, in the backyard, I pulled Kyle toward me by the neck of his shirt and we kissed with tongue in a way that felt like an eager handshake. It was the most platonic kiss anyone has ever had on a hot summer night. We separated after a few minutes, looked at each other and laughed at how ridiculous it was, then went back inside to join the rest of our friends.
The kissing had been so nothing, but I felt immediate guilt for sneaking around behind Adam’s back. The guilt came from a rotten place: I felt dirty and ashamed for wanting any kind of sexual contact in the absence of it from my boyfriend. All the lessons I’d been repressing from childhood about chastity, and how good girls are supposed to be—never wanting and definitely never needing sex—came flooding back. I told a close friend about what happened, and thankfully, she met my confession with compassion rather than judgment. She helped me realize I wasn’t gross for needing my relationship to include a sex life. And also, that the fair thing to do—for both Adam and myself—was to break up with him.
We ended it within a month, and I cried about it every day for a week, then got physically ill and spiked a 103-degree fever. When I told my doctor about what had been going on, she told me that sometimes people get sick after getting through a significant, stressful event—like how college students always get the flu after finals.
This is the part where I tell you that while I don’t regret cheating, it also doesn’t feel great. Guilt is like a gas, in that it will expand to fill whatever container it’s in. I felt the pressure of it building inside of me, and it was painful. Still, regret and guilt are separate feelings, and I know that, given the chance, I wouldn’t do any of this differently. Because otherwise, I’m not really sure who I’d be now.
I think a lot about a line from Brit Bennett’s debut novel, The Mothers: “Most of the milestones in a woman’s life were accompanied by pain.” Each time I’ve cheated has felt bad (to an extent), but also monumental in a productive way—like a milestone. With Drew, I learned that passion is distinct and you know it when you feel it… and also when you definitely don’t. With Kyle, and then the help of my compassionate friend, I learned how necessary sex is in loving someone (at least for me). I’ve learned other things about my sexuality the honest way, but something about being willing to break my own moral code to achieve these epiphanies makes them more precious to me. Like, they must have been worth it if I was willing to go so far.
The third and last time I cheated on a boyfriend was, again, on a hot night. Although, this was the only time I’ve ever cheated on someone with an ex, and the ex was Matt. The complicated end of our relationship (which was much messier than just my hookup with Drew), had been haunting me. And in the years since, this was the first time we’d been in the same place at the same time.
I shoehorned coincidence into fate, and when he asked if he could come by my place at 3 a.m., I said yes. Sometimes, you know something is a bad idea, and that’s why you do it. We spoke in the dangerous language of nostalgia, and closed the gap between our bodies as we did so. We only stopped talking when we started kissing, and I noticed his tongue felt small and cold, like a medical instrument you want to swat away. We had methodical sex, like two people following instructions to assemble a piece of Ikea furniture, and he got dressed and left as the sun started glaring through the mini-blinds. I didn’t feel bad, but I didn’t feel good, either.
I slept badly for a couple of hours, and had a strong desire to shower. When I stepped out into the light, already too hot and bright at 8 a.m., I knew two things: First, I needed to break up with my boyfriend. Clearly, I didn’t feel as strongly about him as he did for me, because where I usually felt the kernel of guilt starting to expand, I only felt sadness.
Second, I’d come a long way since the night on Drew’s bed when I first cheated on Matt. I had learned so much about myself in the years since then—like how it feels to be in love, how a kiss feels when I really want it, and how sex feels when love and wanting it converge. That third lesson is so rare to learn, and perfect when you experience it, how could I ever regret doing any of the things I did to find it?
*Name has been changed.