Henry and I had break-up sex on at least four different occasions, maybe more. I wanted to believe it was because we loved each other that much, when really I was unwilling to read the writing on the wall. It took me years to pry my fingers from his pant-leg and let go of our relationship. In fits of pique I wondered if he was the one who got away, less of a daydream than a deep anxiety that I’d bump into him decades later and love him just as much as I did the day we decided it was the last time. And the next time we decided it was the last time. And the time after that.

We technically broke up in May of 2014 at my college graduation only to get back together six days later when we decided we could overcome the hundreds of miles between Bakersfield and Berkeley. He told me his parents offered to pay for half of the gas required to drive up to see me — it was only when the summer was over that I learned he’d lied and paid for everything himself. We were smart kids who knew long-distance was doomed, but there are some lessons you need to learn for yourself lest you spend the rest of your life wondering if you would have been the exception. We weren’t. It only took us another two months of longing and conflict avoidance to break up again in the kitchen of his parent’s home.

The breakup was not mutual. I scream-cried like someone had died. When I stalked off to sob in the guest room, I expected him to follow me and take it back. Instead he folded his hands together on the kitchen table and clenched them tight, his willpower miraculously holding firm. This turn of events was as surreal as it was humiliating: I sat on the floor and stared at the portraits of his relatives above the heavy antique bed, the extended family I assumed would be mine someday. Two months wasn’t long enough to really try, was it? Two months was summer camp. It wasn’t even a full season. How had he already decided this wasn’t possible? Was I just not good enough to fight for?

We broke up for all the same reasons college sweethearts break up: our lives were taking us in separate directions, and long-distance was as shitty as everyone warned us it would be. I was graduating. Henry, two years younger, was moving to Asia for his junior year for an ambitious study-abroad program, and he didn’t want to be the guy always on his phone. I was reeling with post-grad identity issues and undiagnosed anxiety and depression, and I often called him crying while my roommate scowled outside my bedroom. Once when my laptop stopped working, I had a full tilt panic attack over FaceTime as he helplessly Googled Apple store locations near my apartment. Simply put, I was a disaster and we were young. It was too much for him to handle and too much for me to understand, and I took our generic problems personally instead of seeing our breakup as the natural progression of events. All I could believe at age 22 was that he’d given up on our future together, and it must mean I wasn’t worth it after all.

The first time we had breakup sex was that September. By that point I’d admitted defeat in the Bay Area and moved back East to live with my mother, commuting three hours on the train each day to Manhattan for an internship in social media. My plan was to eventually return to the publishing industry, but I needed an excuse to move back to New York beyond “My boyfriend broke up with me and I don’t know how to make friends.”

The internship was paid and prestigious, and it didn’t include getting anyone coffee. My copywriting was good and my boss was kind. Confidence began to bloom in my stomach, its petals delicate but colorful.

Henry returned to campus for a week to celebrate his 21st birthday with his friends before he left for Asia, and I drove up to see him. We sat across from each other at Wesleyan’s café-bookstore, flirting warily and unable to stop smiling. He was nervous, his eyes saucer-wide and wet. I preened in my pink faux-leather jacket and bragged about my new job. I wanted him to be impressed, to realize what a mistake he’d made, but mostly I wanted to take his hand on the table and squeeze it. My fledging life in New York faded into irrelevance looking at this boy I loved. I wasn’t over him and I didn’t bother to pretend to be.

After an hour or so of polite small talk and careful banter, Henry offered to walk me back to my friend Rachel’s dorm where I was staying the night. He would be crashing on our friend Felix’s couch. We mentioned these details furtively during conversation, little Morse code clues to be translated only if we shared the same motives. I had no expectations of my visit other than to see him again, and I was petrified to assume too much and leave myself exposed, once again the desperate ex-girlfriend on the guest room floor.

I didn’t need to worry: we swung together easily like the glass prisms of a wind chime. In a characteristically bold and vulnerable move, he reached out and wove his fingers through mine when we stepped out of the bookstore and into the crisp fall air. That one touch was enough for us to give in to the giddy longing and relief of seeing each other again. When he hugged me, neither of us knew how to let go. He buried his face in my shoulder and I almost felt guilty about it, how normal it felt, how little I wanted to pull away. When he kissed me, I let out a whimper of crushing need for him, and for him to need me.

We stayed up most of the night curled together in Rachel’s twin XL bed — she stayed at a friend’s place to give us privacy. I don’t remember how it started, who kissed whom, or what terms we agreed to. The feeling was what stayed with me: relief and overwhelming gratitude. I binged on Henry’s skin, kissing his shoulders and his wrists and his mouth. I wanted to come home to every notch on his spine and scar on his hips.

We were drunk on desperation and missing each other. Each touch and kiss carried the weight of every touch and kiss we’d shared before. Our time apart left me thirsting for his mind and his laugh and his warmth, and I knew I had to bottle up as much of him as I could to make that night last. I had him with me every day — every single day — for so many months, and now I would not anymore.

Somehow he distracted me from that terrible pressure, that already aching pain. It was a lucky curse to think it was the last time, blissfully sad and messy and hungry.

He asked what I was thinking and I said, “I shouldn’t say,” and he said, “No, probably not.” We behaved for maybe a half hour until that same verbal compulsion I felt when we first fell in love began creeping up my throat. During a Valentine’s Day health disaster in the emergency room, I had told him I loved him for the first time. Seeing him in his mint green hospital gown, it erupted from my mouth like a sickness, I’m falling in love with you. Was that only seven months ago? Less than a mile from here?

“Déjà vu,” I said. He looked at me with his boyish face and freckled shoulders, open-hearted despite his better judgment, and I finally let it out. “I love you.”

The dam broke. We’d already said it that night in a million different ways, but actual words always up the ante. Just like he’d reached for me first, I spoke first, and he followed me as I followed him.

“I love you too.”

It escalated from there, the old words returning to us not even rusty from disuse.





We made promises we were too young to realize we couldn’t keep. We talked about the future we still wanted and the feelings we still felt. The love spilled out of our bodies like our inside jokes. It turned out we had lived our lives in miserable parallel even as we pulled apart, and now here we were, overlapping for a night in a borrowed bedroom and crushed, impulsive kisses in parking lots. Six weeks without touch wasn’t enough to unlearn this language.

It made me feel better to hear how much he still loved me, how much it had hurt to say goodbye. I wasn’t alone in my heartbreak. I wasn’t stupid for my incoherent shock back in his parents’ kitchen. He loved me more than anything and anyone.

In the morning, when he tied his shoes on the linoleum floor and reluctantly put on his jacket, I could make peace with him leaving this time. I wasn’t blindsided. That last night felt like a real ending, mutual and kind. My hair would smell like him all day and that could be enough for me, surely. I could stuff his words of love into my pockets and bring them to work with me. I could live through the night, and through tomorrow, and eventually through the year.

As I watched him walk across the parking lot, my palms pressed to the window, I tucked away those love-drunk promises to see each other when he returned from Japan for his senior year at Wesleyan. I couldn’t tell if he looked back at me because there were still leaves on the trees — at a certain point all I could make out was the brown canvas of his coat and his dark hair. I believed with the absolute faith of the devout and the smitten that we would get back together next summer. Because Henry said so.

The problem revealed itself in time: I still didn’t think it was the end, and it wasn’t really. It was just the end of us having a real shot.

Breakup sex is a dangerous proposition. At its best it is a balm for a broken heart, soothing it after so many hurtful words and abandoned promises, to reveal whatever residual love still breathes underneath. Sometimes breakup sex instead pours acid in the wound, burning away any regret or longing. When it’s a volatile mixture of both, that’s when you know you’re fucked.

Ideally sex between ex-lovers is a cathartic release, a mutual opportunity to create something out of the ashes and move forward with acceptance and less pain. Here is this person whom you know differently from everyone else, this person you’ve shared something with, and you’ve already said goodbye but discovered there is more left to say. Sex can be a vital language for two people who have run out of words, or for whom words are cheap and ineffective, unable to capture the wealth of tangled emotion still living in their chests.

I want you but I can’t give you what you want. I want you but this is the wrong time. I want you but we’re incompatible. I want you but this isn’t enough. I still love you and it breaks my heart that that doesn’t matter.

There is nothing less casual than casual sex with an ex-partner. That’s true if it’s a mad dash fuck or slow, honest love. Breakup sex is a beautiful lie we tell ourselves: that this will solve everything. That we will feel better and understand more on the other side. There is finality in how they taste, a scarcity in how you reach for them and pull them closer. This is it: memorize their breath and the stretch of your limbs and their sweat on your breastbone. Our desperation to forget the relationship is almost over is mortifying, but it’s a relief to endure it together.

We did not get back together the next summer. We did, however, have breakup sex again in July. I visited him during his summer internship in Boston for a heartbreaking weekend that he’d intended as a lighthearted romp down memory lane and I assumed was a serious romantic gesture. Both of us were left disappointed and hurt, almost comically hung up on each other but needing different kinds of comfort. Most of the weekend was spent crying, interspersed with visiting Boston’s tourist spots in a downpour of rain. We watched the Fourth of July fireworks over the harbor and with each colorful explosion I thought He doesn’t want to be with me and I waited for nothing and This is the end. I felt pathetic in my intentionally planned take-me-back outfits. The sex was brittle and removed, clarifying in its disconnection.

I went back to Brooklyn all wrung out and confused. What memo had I missed? When had we agreed to get over each other and just be exes who bang for fun when we’re back on the same coast? How did we go from best friends, partners, maybe-someday-spouses, to those exes who make a scene crying at restaurants? My ego damaged and my heart bruised, I swore him off for good, comforted only by the sight of the Manhattan skyline as Amtrak raced me home.

But then I returned to Wesleyan in October to speak on a Homecoming panel and I remembered what home really was. Home was still the emerald green of Andrus Field, breakfast pails at WesWings. Home was Henry texting to offer a tour of his and Felix’s lodging in Senior Village. They’d been assigned one of the old wood-frame houses and it overflowed with baking supplies and video games and their impressive vinyl collection. Henry peacocked with nervous energy as he walked me from room to room, firing off wordplay and jokes about his senior thesis. It was awkward at first and then not awkward at all.

The three of us settled in the living room and watched clips of Key & Peele on YouTube until it got late. Felix intentionally sat between us on the sofa but it didn’t make a difference. Henry fished his phone out of his pocket and texted me, “You should stay the night.”

When Felix finally gave up and said goodnight, leaving us alone, we lunged at each other.

Breakup sex with Henry was always this shocking and totally inevitable collision. After our misfire in Boston, this homecoming felt like we were setting the record straight. We were under no illusions about long-distance or picking up where we left off. Our lack of expectations kept us honest: we were borrowing each other, and we were lucky.

It was becoming clear that we were growing in different directions. Only a few weeks before, my activist work was featured on Buzzfeed, and I struggled to recognize myself in the sensational headline: This 23-Year-Old Has Herpes and Wants You to Know About It. In an effort to redefine myself, I’d cut off most of my trademark long hair, but it didn’t matter. All that day, Wesleyan students recognized me around campus. One bro went so far as to yell, “Hey herpes girl!” as I walked past SciLi.

When I asked Henry what it was like to be back at Wesleyan after a year abroad, he said, “It’s weird.” His voice was a little twisted. “Everyone knows who you are.”

This time, our sex was enthusiastic and gentle, an all-night mess of laughter and secrets and music recommendations and gossip. But it was simply being with Henry that centered me. No one ever tells you how banished you feel after a breakup, how exposed to the elements you are without your former partner’s safe haven. Before Henry, I was never loved so fully, with puffy morning eyes and unrelenting acceptance. With Henry, I’d learned what it was to be secure.

I missed his violent, full-body laughter. I missed the sticky warmth of him holding my hand as we dozed.

That year was an extended myth of moving on.

The last time we had breakup sex was honest and humiliating. Four weeks later I drove back to Wesleyan to workshop an essay with Felix, which was both true and a convenient reason to see Henry again. Our night together in October was so good, so genuinely fun — the two of us back on the campus where we’d fallen in love — and I couldn’t leave well enough alone. It was too close to what I had fantasized about all of last year, convinced we’d get back together once summer came. He’d have a little bedroom at the back of a house in Senior Village and I would drive up every other weekend to write tweets and edit essays from the comfort of his unmade bed. There would always be fresh coffee and his Japanese flashcards littering every flat surface. Silly monster movies and sleeping in his Henley shirts. Diet Coke and fresh pancakes.

At age 23 I worked hard to recast my stubbornness as strength, a determination discouraged in young women who are sexually active and assertive. I would have to learn the hard way that you cannot pressure love into submission. People do not remain ours forever.

Like an idiot, I hadn’t asked Henry if it was okay for me to visit. I assumed Felix, his roommate, squared away the arrangements in advance. But the mood was off as soon as I arrived; Henry was busy at the library working on his thesis and then vanished into his room when he got home, the door firmly closed. That evening, all of us went to a house party next door, but Henry stayed in the kitchen, flirting with someone else and holding court. It was the first time he ever avoided me and the public rejection stung. Reality began to settle in then, that I still loved him and that he might not want me to. That he wasn’t the same sophomore boy preserved in resin, who once promised me always. It had never crossed my mind that he might not even want me there.

I snuck out of the party and stood on the front porch, breathing in the Connecticut chill. The weather was just turning and I’d neglected to wear a coat, focused instead on looking smart and intimidating. I was trying too hard — I could feel it as laughter spilled out of the house behind me. Not once in our relationship had I ever chased Henry; we met in the middle over the Talking Heads and fierce political convictions. To be reduced to this, a desperate loose end, brought back the raw humiliation of the day we broke up. It was the kind of pain that lodges itself in your throat like a broken light bulb, shards of glass pressing into your larynx.

Where I would spend the night hadn’t been discussed yet, but I let myself into Henry’s bedroom and borrowed one of his shirts to sleep in. I turned off all the lights except the reading lamp on his desk and I brought a book with me to bed, a prop I ignored as I sulked. He stayed out late in an attempt to avoid the sticky emotional residue that I’d left on his life. When he came back, he stood in the doorway and stared at me, backlit by the fluorescent ceiling lamp in the hallway. I couldn’t see his face, but his shoulders were tight and resigned.

The sex was good but heartbreaking. We were rough with each other, irritated by ourselves and how irresponsible and human we were turning out to be. The romance between us had cracked like costume theater jewelry.

“Do you want me?” I asked, less dirty talk than a plea to be reassured, to be chosen. Years later he would admit that he misheard me and thought I asked, “Do you love me?”

“Yes,” he said. He looked at me hard until I closed my eyes.

I had convinced myself that I didn’t want to get back together but Henry knew me better than that. When he told me this couldn’t happen again, that I couldn’t keep coming back to Wesleyan to see him, the rejection lit up all those old wounds. But I could hear the fear in his voice. I remembered how he cried so hard at my graduation that it looked like his skin was melting off his face. It wasn’t that he didn’t want me here; it was that he didn’t want to want me here. He wasn’t ready for this yet, still healing in his own private way. We loved each other, would probably always love each other, but this once revitalizing love now threatened to hold us back.

I couldn’t ignore it anymore: our paths were diverging widely and permanently. I was working on a TEDx Talk about herpes stigma, and he was deciding whether or not to go to graduate school. It didn’t make sense, the sex writer and the aspiring politician. We were moving forward separately, making plans, and there were other people in our lives who would teach us more about ourselves if we freed up the space for them. There was that girl at the party who would be his next great love, and the rebound waiting for me in Brooklyn who was getting tired of my commitment issues. By returning to Henry again and again and again, I was playing hooky from adulthood, stealing a love that didn’t belong to me anymore. He was asking me to let him go.

It was awkward in the morning as we got dressed. Neither of us wanted to think about the end. It was weirdly anticlimactic for such an earth-shattering goodbye.

Before he could disappear downstairs to cook pancakes for the house, I grabbed the front of his shirt and pulled him down to my level. I perched on my tiptoes and wrapped my arms around his neck, seized by some frantic fear. Obedient, he leaned down to twine his arms about my waist. I snatched from him a beautiful, honest kiss, one of those miracle kisses that exist purely for the kiss’s sake. I knew without accepting it that this was the last of him I would own, and he gently asked, “What was that for?”

I am in love with you and I do not get to keep you. The thought of the moment after this one ends is too painful to consider. Kiss me, again. Say my name the way only you do. Don’t stop. We cannot stop.

I shrugged.

“Just felt like it,” I said.

© 2020 Ella Dawson. First published in Longreads.

Photo credit Ava Sol.

This essay was first published by Longreads in 2020. I’m republishing it here because it’s emblematic of the work I hope to do on my Patreon. I want to write about the fragile intimacy that exists outside of capital-R Relationships; the life-changing one-night-stands and the lovers who hurt and change and heal us. This essay, originally titled The Lie of ‘One Last Time’ with My Ex, is about love and desire after a breakup — a relationship doesn’t end after two people are no longer committed to each other. The relationship simply changes forms, and if you’re lucky, it remains something beautiful. Join my Patreon community now to read more of my sex writing and invest in a healthier culture of casual sex.

Posted by

Ella Dawson is a sex and culture critic and a digital strategist. She drinks too much Diet Coke.