Lena Dunham, Shannon Woodward, Miranda July and Sarah Silverman write about their first time


When I was about nine I wrote a vow of celibacy on a piece of paper and ate it. I promised myself, in orange magic marker, that I would remain a virgin until I graduated from high school. This seemed important because I knew my mother had waited until the summer after she graduated and also Angela Chase seemed pretty messed up by her experience at that flophouse where high school kids went to copulate. If my relationship to liver paté was any indication, and I had recently eaten so much that I barfed, then my willpower was very bad, and I needed something stronger than resolve to prevent me from having intercourse too early in life.

Turns out, this was an unnecessary precaution. The opportunity never arose in high school, nor even during the first year of college, save for a near-miss with a stocky kid I knew who was home visiting New York City from the Air Force Academy—that encounter went far enough that I had to fish a mint-colored, never-used condom out from behind my dormitory bunk bed the next day. I transferred to Oberlin my sophomore year, a small liberal arts school in Ohio that was known for having been the first college to admit both women and men, as well as for its polyamorous, bi-curious student body. I was neither, but it did seem like a good environment in which to finally get the ball rolling. I really felt like the oldest virgin in town, save for a busty riot grrrl from Olympia, Washington, who was equally frustrated; she and I would often meet up in our nightgowns to discuss.

I was pretty sure I had already broken my hymen in high school, crawling over a fence in Brooklyn in hot pursuit of a cat that clearly didn’t want to be rescued. So the event would only be psychologically painful.

I met Jonah* in the cafeteria. He was roommates with an emo kid who worked at the video store and had a crush on my best friend, Audrey. Jonah didn’t have a very specific style beyond dressing vaguely like a middle-aged lesbian. He was small but strong, with floppy hair and warm eyes. He reminded me a little bit of that Air Force kid, who had rejected me in a saga too long to recount here. Something primal kicked in, like an Alfred Hitchcock character hell-bent on replacing his dead wife with a lookalike, and I resolved to make him mine.

The best way was obviously to throw a wine-and-cheese party, which I did, in my 8×10-foot room on the quiet floor of East Hall. Procuring wine entailed a sub-zero bike ride, so it ended up being beer and cheese and a big box of Carr’s assorted party crackers. Jonah was “casually” invited in a group email that made me sound a lot more relaxed than I actually was. And he came, and he stayed, even after the entire gang had packed up and gone. We talked, at first animatedly and then in the nervous generalizations that substitute for kissing when everyone is too shy. Finally, I told him that my dad painted huge pictures of penises for a job. When he asked if we could see them online, I grabbed him by the scruff of the neck and just went for it. I removed my shirt almost immediately, and he seemed fairly impressed. Wearing just a too-tight slip-skirt from the local Goodwill, I hopped up to get the condom from the “freshman survival pack” we had been given (even though I was a sophomore).

Meanwhile, across campus, Audrey was in a private hell of her own. She had been waging a cold war with her roommate all semester: the busty, ren-faire loving Philadelphian was the lust object of every LARPer and black-metal aficionado on campus. Audrey just wanted some quiet time to read political texts and iChat with her boyfriend in Virginia. Audrey’s roommate was now dating a kid who had tried to bake meth in the dorm kitchen, warranting an emergency visit from men in what looked to be space suits. Before going out for the night, Audrey had left her roommate a note: “If you could please have quieter sex as we approach our midterms, I’d really appreciate it.” Her roommate’s response was to burn Audrey’s note, scatter the ashes across the bed and floor, and leave her own note: “U R a frigid bitch. Get the sand out of UR vagina.” (Sounds like Audrey's roommate could have been an ONTD reader tbh)

Justifiably distressed, Audrey headed back to my room hopeful for a sleepover. She was sobbing, and disoriented, and also pretty sure I was alone finishing the cheese, so she flung my door open without knocking. There she found Jonah on top of me doing what grownups do. She understood the magnitude of the occasion and through her tears shouted, “Mazel tov!”

I didn’t tell him I was a virgin, just that I hadn’t done it “that much.” It hurt a little more than I’d expected but in a different way, and he was nervous too and he never came. Afterwards we lay there and talked, and I could tell he was a really nice person. I commended myself for making a healthy, albeit hasty, partner choice. I really couldn’t wait to tell my mom.

Jonah wanted to date, and I figured out pretty quickly that I did not. I went over to his dorm and broke up with him in the laundry room, sitting on top of a running washer. He seemed genuinely hurt and perplexed, and I told him I’d been a virgin because I thought it made me seem like less of a she-devil. Later that year, Audrey saw him in the student post office picking up a package with a pair of used Merrills to replace his really used Tevas, and we laughed about it like mean girls.

Jonah and I only had sex once, but it was enough to convince me that it wasn’t that hard to make it happen. I had, for the past few years, set my sights quite purposefully on boys who weren’t interested, because I simply wasn’t ready (despite all the movies about wayward prep-school girls I liked to watch). I had been waiting because I wanted to, and then suddenly I was ready for the change in identity I was sure would come with no longer being a virgin. But afterwards I still felt very much like myself. Although it’s amazing how permanent virginity feels, and then how suddenly inconsequential. I barely remembered the sensation, the embarrassment, and the urgency. I passed the riot grrrl arm-in-arm with her boyfriend senior year and we didn’t even exchange a nod of understanding.

Later, I wrote that virginity-loss scene almost word for word in my first feature film, Creative Nonfiction, minus the part where Audrey busted the door down. When I performed that sex scene, my first, I felt more changed than I had by the actual experience of having sex with Jonah. Like, that was just sex, but this was my work.

Name changed to protect the truly innocent.


Kevin Brennan was the emcee on open-mike nights, Mondays, at the Boston Comedy Club in the West Village of Manhattan. I had a job passing out flyers for the club every Thursday, Friday, and Saturday from 4 PM to 2 AM, and besides my 10-dollars-an-hour payment, I could go up on open-mike night without bringing two friends (a prerequisite for open-mikers was that they had to bring two paying customers).

Kevin was tall, with dark brown hair and a white-and-red blotchy Irish face. He wore a long army-green trench coat and carried a briefcase, which, at 19, I found very impressive. And he was 30—a grown man. He stood outside the club smoking a Merit Light. I went outside and bummed one.

KEVIN: So, you go to school?

ME: Yeah. NYU.

KEVIN: What—are you a freshman?

ME: Mm-hm.

KEVIN: What—are you, like, in a sorority?

ME: Yeah, but you can only be in it if you’re really cool.

KEVIN: Yeah? Who else is in it?

ME: Just me.

He laughs.

Let me take a moment to describe myself here: big curly perm, black polyester shirt with long sheer sleeves, black miniskirt, and Doc Martens with thick black soles. It was 1990.

I did my five minutes and stayed for the rest of the night until the show was over and Kevin was going home.

“You wanna see my apartment?” He chuckled, I assume at his paper-thinly veiled offer. “It’s in Queens.”

“Sure. Yeah.”

And off we cabbed to Astoria, Queens. We walked up a stairwell and through a hallway to his apartment. It smelled good to me. It smelled like first grade for some reason. Something industrial but sweet, like old paint and licorice. Inside there was a small living room, a bathroom, and two bedrooms—one his and one his roommate’s. On the coffee table was a Best of Chicago tape. He also had a stack of records, with the Go-Go’s Vacation on top.

“Wanna see my bedroom?”


He led me to his bedroom—a bed, a dresser, and an ashtray. He kissed me while he laid me back in his bed.

“Have you ever had sex before?”

“Yes, I’ve had sex before,” I said, insulted.

Here’s the thing. I thought I had had sex.
My senior year of high school I visited my sister Laura at Boston University, and she fixed me up with a friend who was from all accounts very good-looking. I knew he was the kind of guy girls in my school would think was really hot. He was in college; he was tall and lean and had long hair and a long beard—like a sexy Jesus. We sat on my sister’s tiny living room couch and watched Dead Ringers, a creepy Jeremy-Irons-as-twin-gynecologists thriller, and fell asleep before anything really serious happened. The next morning my sister and her roommate left early for the AIDS Walk, and this guy and I—yipes, I can’t remember his name, maybe Brooks or something like that—moved into my sister’s bedroom. He put on a condom and pushed against me, but there was honestly no hole there. I figured that was it. The guy just pokes hard between your legs for a while. Sex. When he finally gave up, he said, “It’s not like it is in the movies, Sarah. Is that what you thought?” Which was as weird thing to say right after watching Dead Ringers.

“No,” I said defensively.

So when Kevin asked me if I was a virgin, I answered honestly: no. Somehow I think he knew better than me, because he pretty much instructed me through the whole process. He talked me through my first blowjob (that, I admitted I had never done before), what to do with my tongue, what not to do with my teeth, and so on. And then, slowly at first, he pushed inside me. All the way inside. And all I could think was,

Holy shit, THIS is sex, dummy.

He sat up on the side of the bed to smoke another Merit Light, carefully ridding the end of any excess ash, molding the red tip of it into a constant point. He put out his cigarette and pulled back the sheets to get up, revealing a Rorschach-like pattern of blood. Like a red butterfly stamp, getting lighter and lighter with each imprint.

There was a long moment of silence before I worked up the moxie to say, “That came out of you.”

“Um. No it didn’t.”

Another long pause, broken by him: “It’s OK. Just buy me new sheets.”

Kevin didn’t have much time for me, but I took whatever I could get. I couldn’t wait to have sex again and again and again. It was awesome. I was in love.

The feeling wasn’t mutual. As it turned out, there’s a reason 30-year-olds sleep with 19-year-olds, and it’s not because they’re looking for something real. I beautified myself in my dorm room, checking the time and myself alternately all night for a date with him that never happened, and when I saw him next and accused him of sleeping with someone else that night, he just said, “It wasn’t my fault she tricked me,” with an I don’t give a fuck half-smile.

After six months of being his if-he-couldn’t-find-anyone-better fallback sex, I gave him a letter with the ultimatum that he had to be nicer to me or it was over. He opened it immediately and read it in front of me, and said, laughing, “Then I guess it’s over.”

Not long after that my friend Kerry came to visit me from Washington. She asked me how I was and I told her that I lost my virginity but the guy dumped me and I was devastated.

“Fuck that shit,” she said. “I’m a female chauvinist.”


“I’m a female chauvinist. I tell a guy, ‘When I’m with you I’m with you, and when I’m not with you, you don’t worry about where I am.’”

I was inspired. Kerry changed my perspective—changed the way I saw men and changed the way I saw myself, transforming me from prey to predator in one weekend visit. For the next two years I was on a rampage. I was a monkey swinging from vine to vine. I kept Noxzema in my bag because I never knew where I’d end up sleeping or with whom. (Another rule from the Book of Kerry: never go to sleep with a dirty face.)


I was 17, a senior in high school. He was 27, a grad student at UC Berkeley, the local college. He was actually my friend’s boyfriend before he was mine—I guess he just really loved girls from this one particular prep school, and the feeling was mutual. My friend was somehow not really mad. I remember her describing birth control to me, which was “the sponge,” a chemical-soaked sponge that you stuffed up your vagina. He was from Detroit, kind of a big guy, looked a little like a boy from The Brady Bunch gone bad. He was so poor that he did not even have a bed, just a blanket neatly laid out on the carpet of his friend’s living room. So that’s where we did it.

I visualized outer space to block out the pain, a fact I only remember because I included it in a story I wrote afterwards. I typed it up on the family computer and stupidly named the file The First Time. Later that week my mom took me out to a special lunch where she asked me if I’d had sex. I think she was surprised it had taken me so long. A few years later, she casually suggested that I had a lover I was visiting on my “long walks.” But they really were just long walks. We went out for a few months. It was an intense, formative time for me. I was thinking very hard about everything, including, but not only, feminism. One night I suggested we drive up to the hills overlooking the city. We parked and stood together on the edge of a cliff. I asked him to go down on me while I looked at the view. When he stood up again, I broke up with him.


I’m not quite sure how I missed the boat, but the boat was missed. By boat, I mean the kissing boat. The seven-minutes-in-heaven canoe. The spin-the-bottle pontoon. The makeout-party ocean liner. While all of the teenagers I knew were out honing their kissing skills, I was most likely home watching reruns of I Love Lucy and trying to figure out how to effectively blow-dry my terrifyingly woolly hair. In hindsight, this hair quagmire might have genuinely contributed to my late-blooming debacle. I digress. Suddenly, more people were making out in the hallways during passing periods than I believe actually went to my school. I was desperately behind the learning curve of love. I was doomed.

After giving my predicament a lot of thought, I came to the conclusion that the only acceptable thing to do to ensure the stability of my reputation as a relatively cool human being would be to somehow kiss a boy who was separated from my school life by at least 500 degrees. That way, if our make-out ended in some kind of terrible explosion, death, or hostage situation, I could easily pretend it never happened. Enter Trent.

Trent from my high school. Trent from almost every single class I was enrolled in. Trent who was surely my soul mate. Trent with his Johnny Depp hair, his ability to play nearly every Goo Goo Dolls song on his guitar, and his keen instincts as to exactly what methods of ignoring me were sure to make me swoon. Oh, yes, Trent. We were destined to be in love. Because, above all else, Trent was in a BAND. My ingenious plan for learning how to kiss in secret was immediately abandoned. I had a target.

After weeks of shameless flirting on my part (asking sporadically to borrow notebook paper and saying hello at a volume audible only to baby cats), Trent finally asked me to hang out with him outside of school. His band was playing at the community center at the local park. Please keep in mind that at this point, playing the community center was, to me, the equivalent of gigging at Madison Square Garden. This guy was my Mick Jagger. But, shorter.

I dressed up in my coolest outfit: a pair of leather pants from the Gap, and some kind of ratty lace tank top that I was convinced made me look like Courtney Love, and certainly not like some kind of sad homeless child (it made me look a little bit like a sad homeless child). I spent the entire day studying Rayanne Graff from My So-Called Life and methodically ripping off her “cool girl” expressions (these mostly consisted of raccoon-like stares with the occasional ironic eyebrow raise sprinkled in). With my newly acquired repertoire of faces, I set upon my mission to persuade my future husband to love me.

Everything happened like in a dream. Trent and his band performed: they were transcendent. I was convinced he was the next John Lennon. He glanced at me while he sang, and I practiced my unaffected “this happens to me all the time” half-smile, while in reality I think I blacked out for a sliver of a second more than once. He even played my favorite song, and dedicated it to me (“If You Could Only See” by Tonic—don’t judge me). When it was over, I went backstage (aka the bathroom area of the community center) to find him. He was putting away his Yamaha and running his fingers through his glorious teen-heartthrob hair when he noticed me.

“Hey Shan, what’d you think?” he said.

“You were all right,” I replied, praying that he understood my sarcasm.

“Yeah?” He stood up and moved very, very close to me. I’m dead. Paralyzed. Surely not capable of speaking English at this point. I remembered the advice that my earth-science teacher, Mr. Finney, gave me should I ever find myself in a confrontation with a T-rex: don’t move. They can’t see you if you don’t move.

Trent put his hands on my hips.

“Wanna be my girlfriend?”

He said that. He really said that. Things like that NEVER happened to me.


That was it. It was going to happen.

It happened.

He kissed me.

IT WAS TERRIBLE. Terrible isn’t even the right word. It was completely disastrous. My moves were all over the place. Imagine someone blasting the “The Hokey Pokey” and “Smells Like Teen Spirit” at the same time in a very tiny, claustrophobic space. Like, say, a doghouse. That is what this kiss felt like to me—all wrong, and rhythmically a mess. Except, throw in wet and spitty. I couldn’t wait for it to be over. Humiliated and panicked, I tried to come up with something to say that would save me from being awarded the title of Most Likely to Never Be Kissed Again in the yearbook. I opened my eyes. Trent looked at me, obviously a little confused by what had just happened, if not rightfully concerned about my mental health.

“Don’t worry,” I said. “You’ll get better.” I patted him on the face, and I walked away.

This stunt may the most insane thing that I have ever done (aside from sleeping in my parents’ backyard for a week and ordering pizza to “tent guest house”). I had tried to make this poor boy believe that HE was the terrible kisser because I couldn’t live with the idea that I might not inherently be God’s gift to every teenage boy’s lips. After all, I was wearing my ultra-cool leather pants and using my brand new as-seen-on-TV facial expressions! How could it possibly have gone wrong?!

I’ll tell you how: I was so caught up in the anxiety of never having been kissed that I forgot to pay attention to my partner in this kissing escapade. He actually wanted to kiss ME, not my newfound neuroses that had become a monster of their own! See, kissing is kind of like a…conversation. It takes two human beings, and it can be an incredibly engaging and memorable experience, or awful and terrible and something you never want to mention again. Kissing is an exchange of spit and tongues and lips that is different with every person you encounter (romantically!) based on their very own human-ishness (look it up). You’ve gotta feel it out to figure it out. I was a crappy, self-involved conversationalist, metaphorically. That realization in itself enabled me to slowly but surely improve upon my make-out instincts out as my angst-ridden teenage years went on. I assure you, plenty of those other moments weren’t pretty either, but, a few of them were incredible. Movie-like, even.

In case you’re wondering, the following morning at school, Trent and I couldn’t make eye contact. I couldn’t bear to face the shame of my own kiss-tastrophe. Our beautiful relationship ended sometime before the third or fourth passing period, through a game of human telephone. He also eventually found out through one friend or another that our community-center rendezvous was my first kiss. To be honest, it wasn’t so bad when he found out. He never mentioned it to anyone. I think he had a little sympathy for me. Not enough to kiss me again, but enough to keep my secret safe.

I’d be willing to bet that Trent had had a first kiss of his own once, too, and most likely his wasn’t so great, either. In fact, I bet nearly everyone at my high school had a similar story. That “learning curve of love” that I was so panicked about? It never really existed. Unfortunately, the hopeless war with my woolly hair does. It’s an uphill battle.

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