Men I Might Regret Sleeping With Were It Not for the Music They Introduced Me To

by Lily Heron

Part ONE: Radiohead

hurt feelings : listening pleasure = 2 : 10

I remember the precise moment I decided I would lose my virginity to someone I did not love. It was a warm early summer day when I walked the 10 minutes down sleepy suburban streets to my friend Jenny’s house, let myself in the front door, and tapped lightly on the closed door to her bedroom. The muffled cries I heard in the hallway resolved themselves on the other side of the door into Jenny, pajama-clad, fetal, sobbing on her plush carpeted floor.

Jenny’s house was not only a refuge from the tumult of my own home but a site for many girlish explorations into the world it sealed us off from. We tried hot waxing our legs sitting on the edge of her tub, listened to Jane’s Addiction while smoking cigarettes on the balcony, and lay on her bed watching David Lynch movies that lingered over the next morning’s breakfast of Dutch babies spread with apple butter. But Jenny had fallen in love one summer when I was visiting my father across the country, and at 15 she had become the first of our circle of friends to have sex. As an insecure fat girl who had never so much as held hands with a boy, I felt like Jenny had become some kind of high priestess of sexual experience — I simply couldn’t fathom that kind of intimacy. Nor could I understand what it was like to get dumped without warning a few weeks before her boyfriend of just shy of a year had left on a school trip for Japan.

Stumbling across violent emotion can feel invasive or embarrassing when it involves a stranger screaming into a cell phone; when it’s a friend you feel a different kind of discomfort. It’s like being a never-nude at the clothing optional hot tub. You know and they know you have the same stuff underneath — you’re just the one trying to hide it. Seeing Jenny in such raw agony, I felt the fragility of our safe adolescent world and the encroaching menace of the world of sex. I didn’t have the stable home life or personal confidence that Jenny had, and knew instantly I couldn’t risk being hurt like that. I resolved that moment, and over and over again for years, that I wouldn’t have sex until I knew I could handle it.

Not that it was much of a challenge to hold onto my virginity when I couldn’t believe anyone might actually want it. The first guy who kissed me was a loner who carried around old catalogs of French Citroën cars and gave me an Einsturzende Neubauten tape. His reward was a ham-handed hand job in a deserted park. After I saw his bedroom, wallpapered in magazine pictures of Kate Moss in various states of undress, I knew there would be nothing more. This boy would only reject me, I thought, but he couldn’t hurt me if I didn’t care about him.

When I moved to a city and started college, I made my first close heterosexual male friends and studied what I thought was their model for sex without romantic attachment. They thought my virginity a novelty and joked that if I didn’t take care of it they were going to have to relieve me of it themselves. But virgins always got attached, they insisted, and I was certain I would prove them wrong.

I got my opportunity a month after my 20th birthday. I was working at a café with my friend Tim when his best buddy from high school came in. Benjamin was back home for Christmas from his fancy liberal arts school. He was boyishly handsome, transparently flirtatious, and super smart in that obnoxious college-age way. I found him charming but also a bit irritating — his sense of humor was juvenile and his attention span short. I couldn’t fall for this guy! He was perfect. The act itself was unremarkable, but I was triumphant. Being the last among your friends to lose your virginity is like being the last to turn 21 — everyone has been waiting to welcome you on to the team. My best friend presented me with a trophy he bought in Chinatown, and I immediately started planning my next conquest.

But there was a hitch. I wasn’t, it turned out, any good at conquests. I liked Benjamin and I wanted him to like me. More than that, I wanted him to be consumed with thoughts of me. I pretended to be totally cool about things around Tim while secretly hummingbird-alert for any and all information. After I managed to casually borrow and copy a mix tape Benjamin had made for him, I had a specimen for study. I began the first of many campaigns, one like those that would later introduce me to South American futbol, movies about the mob, and the band Pavement. I was going to learn all about what he liked and then he would not be able to resist me. As it happened, the mix was heavy on songs from Radiohead, a band Tim told me Benjamin was desperate to see in concert. I loved these songs more than any others on the tape and concluded that our shared taste in music must mean that our souls were bound to understand each other.

I saw Benjamin only once more. I had traveled the three hours south to the town where his university was, ostensibly to visit a friend from high school, but with a powerful hope that I would win him over on his on turf. It was awkward and alienating. I didn’t fall in love with him, but I did feel changed.

A speaker once visited my junior high school to caution us about the dangers of sexual relationships. I’m sure he talked about STDs and teenage pregnancies but all I remember of it was his illustration of the end of a relationship. Taking two pieces of paper to represent a couple and folding them evenly over each other, he then ripped them apart down the center. By coming together people surrendered parts of themselves and they lost them completely when a relationship ended. That certainly seemed to be what happened to Jenny — she felt she had lost a part of herself, and she missed the real presence of the person who had become a part of her. I’m sure I laughed with my friends about how dorky the speech was but inside I was terrified, imagining that torn piece of paper folding with other torn pieces, being ripped again, and then over and over again until there was nothing left but a pile of scraps.

But that’s not how it really works. We risk a great deal in love and sex, but hopefully we gain more than we lose. Even mere infatuation gives us the hunger, if not always the facility, to see and feel as someone else — to share all of our favorite things and eagerly search those of our lovers for the secrets about them they contain. I don’t believe in fate but I do appreciate the justice done when a regrettable experience begets something wonderful. Or maybe that’s just how I justify my rotten taste in men.

After I discovered Benjamin’s feelings about Radiohead, I went out and bought their then new album, OK Computer, and fell in love. The album filled out the feelings I had about living in the late 1990s, when new political movements were taking shape, and before they crumbled in the wake of 9/11. It was both zeitgeist-y and deeply prescient, the music of ambivalence toward our new algorithmic overlords. I remember listening to the song “Subterranean Homesick Alien” on one of those multi-story escalators in the London tube. Traveling through those bright white tunnels there was a point where you could see neither the top nor the bottom, just brightness and machines. That moment was a hundred times better than the handful of moments I spent with Benjamin. I wonder if he ever saw Radiohead in concert.

“Subterranean Homesick Alien”


Part TWO: David Byrne

hurt feelings : listening pleasure = 3 : 9

When I met Finn, I was in the sexual stage I like to refer to as “raised by wolves.” A loner in high school, I had built a coterie of guy friends in college, looking to them for advice and trying to model their behavior. There is a strong case to be made that this was all the result of internalized gynophobia, but whatever the reason, I thought I was a wolf, wanted to be a wolf, but was most definitely not a wolf. So I tried harder.

Spring break was coming and I threw down the gauntlet: Whichever of me and two of my male friends could first achieve sexual congress (or, ahem, “get laid”) over the break would be treated to dinner by the others. It should immediately be obvious to you that this was merely a battle of who had the lowest standards. As a lady of 21, I could have won that very evening, but as I have explained, I am not a wolf.

Underneath all the bravado I was also deeply and dangerously insecure. I had lost weight since my heaviest point in high school but I could have lost 25 more pounds (as I eventually did) and still had a healthy amount of meat on my bones. What was worse to my mind was that I would always bear the scars of fatness: stretch marks, droopy boobs, cellulite. I was very interested in sex but I was absolutely terrified of getting naked.

Finn was a classmate of one of my friends, part of a big arty circle I was on the outskirts of. I met him first outside a friend’s house and thought him painfully handsome: blue-green eyes, strong jaw, sandy mussed hair, those unjustly long eyelashes that pretty boys sometimes have. The second time I met him was at a party where he was drunkenly passing around his driver’s license, announcing to anyone listening that he used to be fat. I got a hold of the card eventually and sure enough the picture showed him around 100 pounds heavier. My opinion of him shifted immediately.

Someone who has been fat understands things that others usually cannot. They know what it’s like to be a body rather than a person, to be recognized for the single thing that feels least a part of you. I’ve always hated the idea of the mind-body connection. My body has always been in rebellion and my mind has always tried to disown and control its wants and needs. Whether or not it is true I tend to assume that people who have been overweight or otherwise physically marked, especially in adolescence, have a higher capacity for empathy and a greater degree of humility and humanity than the general population. At least this is how I justify my exceedingly inappropriate feelings for hot Neville.

After I knew Finn had once been fat he seemed much safer — less likely to hurt me. I felt he would understand that my body was not me, and that it was not evidence of some moral failing. I was delighted to find that he had stretch marks.

But I’m getting ahead of myself. It was not until the third time I met Finn that warm with drink we stood entangled in the front yard of a house party trying, I’m sure it appeared to pedestrians, to eat each other’s faces off. I followed him home and we fucked on his futon mattress on the floor with the patchy cover of a sleeping bag. Ah college boys. There were a half dozen more such interludes over the next few months, each better than the last. I admired his mind and thought our pillow talk was almost the best part. He introduced me to writers that remain among my favorites today and influenced my thinking indelibly.

But I was far from the only woman Finn had this effect on. It was abundantly clear that he was eager to catch up on all the sex he had missed with women that wouldn’t have noticed him when he was bigger. It never occurred to me to ask for more than the occasional hook-up, mostly because I didn’t think I was attractive enough to hold him. I found confirmation for this when he got a steady girlfriend a few months later — a beautiful, slender, black-haired girl.

This would not be the end of our involvement, far from it, but it was the end of this dalliance. My dude friends were glad. They had grudgingly bought me dinner for my spring break sexual challenge, but they knew Finn wouldn’t be good to me. I knew that too. I had seen enough of his hunger for booze and drugs and general oblivion to know he had a self-destructive streak a mile wide. He was one of those writers who believed he must traverse the darkest recesses of memory and consciousness in order to create, the type one of my friends called “a black hole of emotional need.”

This made it especially strange that the music he brought into my life was so goofy and fun. It was 1998 and the David Byrne album Feelings was in constant rotation on sunny days at Finn’s house, where our group would sometimes congregate. Like many of Byrne’s solo albums, Feelings was clearly influenced by his love of so-called ‘world music.’ It was full of unexpected rhythms and hearty beats, shallow drums, rubbery guitar sounds, and triumphant horns. The album’s standout track, I have always maintained, is “Miss America,” a sunny-day pop song with lyrics that criticize America’s broken promises to the poor and huddled masses by accusing her of serial infidelity.

In the third verse of the song Byrne sings:

And I love America, but boy can she be cruel
And I know how tall she is
Without her platform shoes

I loved the line, despite its unfavorable assessments, because at the time I refused to be seen without my platforms. It was the ’90s, okay? For years afterwards Finn would tell me the song always reminded him of me, that mere phrase containing a reminder of intimate knowledge that made my throat dry and my palms wet. The same song reminded me of him.

“Miss America”


Part THREE: Department of Eagles/David Holmes

hurt feelings : listening pleasure = 5 : 10

I’ve never understood the instant rebound. After my hardest break-up it took almost a year before I even noticed other men. I had been so deeply invested and in love with the man that it simply didn’t occur to me to consider anyone else for the position. It might have taken longer to shake this feeling off were it not for the happy opportunity of what I like to call a “transition penis”: an old flame whose familiarity made things easy (and who was conveniently only in town for a week).

It was through this gentleman that I was introduced to Stewart, a local celebrity I had known of for many years before I finally got to know him on a group camping trip. Stewart was known to have a predilection for brainy girls who looked vaguely European, and I was flattered to catch his eye but hesitant about getting involved. This made him all the more persistent in his wooing. We had lakeside picnics focused on ‘bear food’ (mostly berries and smoked salmon), built living room forts under the influence of Robotussin, and once ended up backstage at an Incubus concert because he happened to know the drummer or something.

It was ridiculously fun — even the dirty looks I got from girls who recognized him when we were out together were amusing. I didn’t think it would last long, but I was still surprised by how quickly he dropped me after we started sleeping together. My pride was hurt but I pretended it wasn’t — those days I so badly wanted to be considered a cool girl who just let things roll that I never let on when it hurt or called anyone on their bullshit — even when it was justified.

Nearly six months later, I was helping out with merch for a friend’s art band, not unaware that the band was full of attractive single gentlemen. I wasn’t directing my attention at anyone in particular until two friends took me aside, separately, to point out the obvious fact that the accordion player had been making serious googly eyes at me for weeks. Their comments made me re-evaluate my interactions with Toby, an artist new to the city whom everyone seemed to like. He had certainly been nice — shown interest in me and what I thought about the show (especially, I failed to notice, after he found out I was close to Stewart).

I wasn’t attracted to him at first, but feeling someone’s eyes upon you in the atmosphere of a dark, boozy place or across the room at gatherings is a strong aphrodisiac. My friends all thought he was sweet and knew I’d been heartbroken so they urged me on. One night he hosted a house party and no one seemed surprised that I kept declining rides home, holding my position on the couch in his room and maintaining my best impression of a coquette.

Of course I knew very little about Toby beyond a brief biographical sketch, but his musical choices that night seemed to speak volumes. Early in the evening he played David Holmes’ Come Get It I Got It, an album that to this day remains my No. 1 party-starting album. If there’s a person who can resist its charms, I have yet to meet them. As the party trickled down to a few people Toby announced he was throwing on an album from a band he’d just heard on the radio. It turned out to be the Department of Eagles EP Whitey on the Moon, music that was beautiful, strange, melodic, dissonant, and haunting, lingering in your consciousness well after a song was over.

This was the kind of music that people noticed, the kind that made them ask “hey, who is this?” and pay attention to the answer. It certainly had that effect on me. With retrospect I can see that associating Toby with such undeniably cool music and associating myself with Toby fed my ego and blinded me to most everything else.

There is a particular danger to men like Toby. I think if women had been generally in charge of film-making over the last century rather than men, we would have seen fewer vamps and more secretly villainous men who are charming but not overtly handsome, with a look of sweetness, even vulnerability, that inspires tender feelings. I think it was vanity on my part that led me to subconsciously congratulate myself for seeing past Toby’s short stature and overgrown boyish looks and imagine I saw a warm heart, keen intelligence, and other fine character traits. The danger is that men like Toby often know they have this effect on women. I had walked straight into a trap. Toby didn’t admire me, he wasn’t interested in me or what I thought about anything, he just wanted to sleep with me.

My first clue that Toby wasn’t the gentleman I imagined came during our pre-bed flirtations. I made some stupid joke about how the groupies were probably the best part of being a musician. Instead of chuckling bashfully as I had expected he thought about it a minute and then told me that actually, art groupies were much more plentiful. I was a bit unsettled, but I was also drunk, and I had already made up my mind where the night was going. Toby was better at sex than I had expected, and I found it surprisingly nice to spoon with someone no taller than me.

By the morning I had borrowed a book and we had officially exchanged contact information. There were flirtatious e-mails all through the next week and after a show the next weekend he followed me home. But things rapidly fizzled. I was making all the moves and I couldn’t understand why he wasn’t being more assertive when he had been so interested in me. I tried making up excuses but avoided asking direct questions. I think I knew that if I brought the matter out, the result might not be the one I wanted. It was much safer to be passive and hold onto the possibility that the relationship I hoped was developing actually existed. Spoiler alert: This doesn’t work. Ever.

Toby wasn’t an evil guy, just kind of a jerk. The two of us were basically doing the same thing but with different goals in mind. He wanted to bed me then slide easily into friendship and go on to the next conquest; I wanted someone to date and sleep with on the regular. Both of us suspected the other of wanting something else and responded by going lalalalala-I’m-not-listening and never bringing the thing up for a vote. This is conjecture, in part, but it’s based on the many occasions before and since when I’ve seen my male friends act in similar ways. When I call them on it the exchange usually goes something like this:

“She’s cool — she just wants something casual.”

“But didn’t you guys get matching tattoos?”

“Yeah, but she just came along with me when I was getting a tattoo and she liked the design so much she decided to get the same one.”

“[NAME REDACTED], she likes you!”

“Nah, she hasn’t said she wants anything more”

“But you KNOW she wants something more, right?”

“ — — — — — — — — ”

I don’t want to reinforce gender stereotypes here, just reflect on the tremendously poor communication that seems to characterize ‘hook-up’ culture. I wish I could say this was the last time I failed to make my own wants and needs clear out of fear, but it was not.

It wasn’t long before most of those who had initially been charmed by Toby started to see him in a different light. He was a relentless social climber and name-dropper, an unreliable friend, and a real juicebox when it came to women — the kind of guy who would encourage a lady to move across the country for him and when she arrived say “so … I guess you should find an apartment.”

I consider my experience with Toby the low point of my sexual career, but he’s also the reason I started noticing that even bad dudes sometimes lead to excellent music. In our very short time together he introduced me to what would become one of my favorite albums and one of my favorite bands.

“Sounds Phoney”


“Sailing by Night”

“Family Romance”

Lily Heron has an excellent music collection.