Is There a “Right” Way to Lose Your Virginity?

Supposedly, young girls sit around braiding each other’s hair, fantasizing about their wedding day. Well, maybe my friends were just sluts, but we never did that. We preferred to daydream about our first fuck. Most of us had a similarly delusional script: We’d lose it on a bed of rose petals, to someone “special,” like a romantically morose Gavin Rossdale look-alike or a slightly less depressive Kurt Cobain. Or something equally embarrassing.

But our idyllic deflowering fantasies rarely came to fruition. In reality, most girls from my school lost their virginity slumped against a tree in an apple orchard, bark jabbing uncomfortably into their spines, in between rounds of beer pong. (Not particularly romantic, but kind of patriotic?) First times are so fraught with expectation and often end in disappointment. But is there actually a right way to lose your virginity?

I lost mine at 16, to my boyfriend of five days. He was in the grade below me, with these big Dumbo ears, an Adrien Brody nose, and a body like a stick insect (aka my ideal type). In an effort to avoid our authoritarian parents, we boned in the woods behind our school’s football field. He worked at McDonald’s, and I remember kissing him, thinking he tasted salty, vaguely like french fries. I’d barely taken my bra off when he came into his blueberry-flavored condom. It was far from what I’d imagined. And yet the most profound 26 seconds of my life.

Culturally, losing your V-card is associated with a loss of innocence, but it didn’t feel that way to me. I mean, how innocent can you be if you’ve already watched gang-bang porn, received an unsolicited dick pic, and given a hand job under the bleachers at a JV softball game? But after it happened, I did feel different. It was like the doors to the world had been flung open. It became less about the details of the experience and more about the fact that I’d done it—I had crossed over.

My friend Eleanor, a 35-year-old painter, is one of the only people I know who actually had the classic, fairy-tale virginity-loss experience. But it came with a price. “In high school, sex just wasn’t something I cared about,” Eleanor told me, lounging in her sunny Los Angeles studio. “Plus, I grew up with an older brother who was really proprietary over my sexuality—he was always aggressive to guys who hit on me—so I always has this sense that my virginity was something I needed to protect.”

She casually dated a bit in college, but she never felt like the guy, or the moment, was “right” enough to pull the trigger. “By the time you’re 22, you’re like: Shit, if I’ve waited this long, I don’t want to waste it on a one-night stand with some vodka zombie,” she said. “But it’s a vicious cycle, because the longer you wait, the more of a big deal it becomes.”

A victim of virginity perfectionism, she soon found herself approaching her 27th birthday, desperate for dick. But then she met a guy from work who seemed potentially worthy. After a month of making out in bars, he took her on a surprise birthday trip to Mexico. “He booked us a weekend staying in an actual castle,” she said. “We had this romantic dinner, and then he lit candles and ran a bath with rose petals in it. I was cringing a bit, because I was like, Oh, my God, it’s too scripted! But I got over it. And then we had really filthy sex all night.” Nailed it.

When I asked Eleanor if she was happy she waited for the cheesy mom-porn fantasy, she frowned and said: “On the one hand, I’m glad, because it was a beautiful experience with someone I cared about. But I also worry that, because I started so late, I’m now really far behind. At 35, I’m still figuring out what I even enjoy in bed. Sometimes I wish I’d just fucked a stranger when I was young and stupid, and moved on with my life.”

But speaking as someone who had a more carefree approach to my inaugural rail, I can attest that it’s never entirely uncomplicated. I grew up in a strict Catholic family that subscribed to a classic Madonna/whore narrative. At 13, my grandmother made me pledge that I remain chaste until marriage (specifying that if I didn’t, I would become a crack addict and die alone).

And I bought it. I truly believed I would wait until my honeymoon to bang—just like American heroes Britney Spears and Jessica Simpson, duh. But by 15, I’d taken a sharp turn and was painstakingly downloading the Pamela Anderson and Tommy Lee sex tape on my parents’ dial-up (tbt). Suddenly, my virginity felt like a disease that needed to be cured—ASAP. And when I finally did have sex, it felt less like a YOLO adventure and more like an act of rebellion—which I’m pretty sure dictated my attitude toward sex for years to come.

Boys, on the other hand, face different social pressure around their first time. For young men, purity is a defect, not a virtue. I recently discussed this dichotomy with my friend Ryan, a 37-year-old cinematographer. “For guys, by 17, if you’re not having sex, it’s like: Dude, what’s wrong with you?” Ryan explained.

The summer after his freshman year, Ryan went on a trip to Spain with a high school group. “We landed in Madrid, and a couple of guys and I went to try to find beer,” he recalled. “We wandered into this bar, and there were a couple of women dressed in lingerie. We were like, ‘What the fuck is this?’ Eventually, one of the ladies came and sat on my lap, and suddenly we got it.”

His friends bailed, but Ryan—anxious, excited, and a couple beers in—decided to stay. “The woman looked about 40 and was very kind,” he said. “We worked out a price in Spanglish, and she led me to a curtained-off section behind the bar. She handed me a condom, and I said, ‘I want dos condoms por favor.’ She looked at me like I was fucking crazy, but in my head I was like, ‘I gotta make sure I’m super-safe.’ So I put both on, we started kissing, she got on top of me, and I was done in 30 seconds.” I told him that might be the cutest virginity story I’d ever heard.

One might assume that losing it to a sex worker more than twice your age could be vaguely traumatizing, but Ryan disagrees. “Ideally, it happens with your first love. But I was emotionally immature and had a deep fear of rejection, ” he said. “But since she was a sex worker, rejection wasn’t a concern, so it actually felt like a very safe way to lose my virginity.”

But what does it even mean to “lose your virginity,” anyway? Is it the moment a dick enters you? That feels pretty arbitrary. Especially since, ya know, queer people exist. These days, the question of how to define virginity—and how to define sex, for that matter—is up in the air. Some say for girls, you lose your virginity the moment you break your hymen. (If so, then I lost mine to a shampoo bottle). Once, a lesbian friend told me it was the first time your partner gives you an orgasm. I said if that were true, then I’m pretty sure, like, 50 percent of straight women die virgins.

But if we think of sex as essentially a pleasurable, intimate experience with another person, then the point at which we’ve crossed that line is really something we get to decide for ourselves. And it doesn’t always look how we expect it to.

Case in point: My friend Amy, a 32-year-old literature professor. At 16, she and her first boyfriend of two years collectively decided to cross over. She told me, “We talked constantly about how it would happen—like, ‘It should be on the beach in Hawaii, and we should hold each other afterward.’ I think reading too much Cosmopolitan turned us both into middle-aged women.”

Spoiler: They didn’t make it to Hawaii. In reality, it happened “on a beanbag chair in the corner of my bedroom, surrounded by posters of kittens and Devon Sawa,” Amy said. “We’d already decided what we were going to listen to: ‘Tonight, Tonight’ by the Smashing Pumpkins, obviously.” But at the moment of truth, her butt sunk into the beanbag chair, which caused her knees to tuck up into her chest. And when he went to stick it in, he accidentally tucked himself into the crease between her leg and stomach. Amy recalled, “I was about to say ‘You’re not in the right spot,” but it was too late—he thrust twice and was done. All I could think was: Ohhh, no. And then he stood up and said, ‘We just lost our virginities,’ with this big smile. I didn’t know what to do, so I just said ‘Yes . . . yes, we did.’”

They eventually ended up fucking “successfully,” weeks later, on his rickety bunk bed. But looking back, Amy considers the beanbag incident her first time: “It was essentially dry humping with a condom on, but it was like emotionally I had lost my virginity. In a lot of ways, virginity is a mental thing. It’s a decision you make together with your partner—even if it doesn’t go in.”

We place so much importance on the first time, but maybe that’s because we’re looking at the concept of virginity all wrong. I mean, the whole phrase losing your virginity implies there’s something to lose—our innocence, our purity, our value—rather than acknowledging how a first fuck can open up a whole world of possibilities. The first try is often (and rightly) an awkward, anxious, and low-key painful anticlimax. All the good sex—that comes (cums?) later. So in a sense, there’s something to be said for just getting it over with.