Virginity is Fake, So Why is it Still a Rite of Passage?

In the fall of my senior year of high school, I was the starting goalkeeper on the boys’ varsity soccer team. After beating our arch rivals, the topic of sex came up, as it does with teenage boys on a long yellow bus ride that put us on this side of adolescence. Who was a virgin, we asked each other, and who wasn’t?

My teammates were astonished to hear I was still a virgin. They presumed I’d been having sex for the past two years with my long-term girlfriend, with whom I’d just broken up. My ex and I preferred heavy petting and deep conversations, I said. We just didn’t have that type of relationship.

As a deeply repressed closeted trans girl moonlighting as a typical white suburban American boy, what else could I say? What excuse could be as passable as a letterman jacket and a soccer ball ricocheting off my chest?

On that cold Massachusetts night, the back of the bus warmed only with our breaths and bravado, my teammates made a bet not so much with me but about me. Would I lose my virginity before prom?

My face flushed bright red when someone asked the question, and the others jumped in with their answers. I wanted nothing to do with this “bet” and said whatever I needed to say to change the subject. My life was not another late-'90s movie where the jock is in on the plot.

However, the stupid bet haunted me throughout the school year. Every couple of months one of my friends would ask me how I was progressing, and my humiliation came rushing back to me. I felt like Jim from “American Pie.”

The first “American Pie” movie hit theaters in the summer of 1999, ushering in my junior year of high school and Y2K. The plot revolves around a group of high school boys who make a pact that each will lose their virginity before the end of their senior year. The film then tracks the various hijinks and debauchery the boys go through to accomplish their singular goal: penis-in-vagina sex.

I found myself identifying with Jim, played by actor Jason Biggs. Jim has, by far, the most awkward narrative arc. His highlight reel includes having sex with a freshly baked apple pie against the kitchen counter, then trying and failing to sleep with a beautiful foreign exchange student (we’ll get to how poorly that scene aged), and finally fucking his band geek prom date. She only accepted his invitation because Jim would be an easy lay—a “sure thing,” ceding some agency to a woman in the movie.

Like Jim, I had no sense of execution. The first time a girl ever let me stick my hands down her pants, I couldn’t even find her vagina. Not her clitoris, like all the jokes and memes say—I couldn’t find her goddamn VAGINA.

At one point late in the movie, the peer pressure gets to Jim and he sort of explodes. “I am so sick and tired of all this bullshit pressure,” he tells his friends. “I've never even had sex and already I can't stand it. I hate sex! And I’m not going to stand around here busting my balls over something that, quite frankly, isn’t that damn important.”

Same, Jim, same.

From my earliest days, sex was an awkward and humiliating concept to me. Despite its reputation as a sexist film, “American Pie” helped me understand that I wasn’t alone in how I thought about and experienced sex.

I rewatched “American Pie” the other day to see if it still holds up. Much of it doesn’t—especially the scene where Jim ends up broadcasting his failed hook up with the foreign exchange student Nadia over the internet to the entire school without her knowledge or consent. I want to be clear that this scene is abhorrent and extremely dated; it also fits the modern legal definition of revenge porn.

Having said that, rewatching “American Pie” and reevaluating a lifetime of sex has convinced me that virginity is fake.

Like Jim, I had no sense of execution. The first time a girl ever let me stick my hands down her pants, I couldn’t even find her vagina. Not her clitoris, like all the jokes and memes say—I couldn’t find her goddamn VAGINA.

You could say that I’m a veritable expert on virginity. After all, as a post-op trans woman, I’ve lost mine three different times. Historically, virginity was valued as a signifier of a woman’s purity and commitment to paternal family order. A woman’s life in western medieval society was defined by the men in her life. At the time, it was a deeply held belief that a woman belonged to the man who first had sex with her, like a piece of property.

In other words, a woman lost value on the marital market if another man had a pre-existing claim on her. This was the origin of the shame cycle women now face when misogynist men cry on the internet about a woman’s “body count.” A woman who is unafraid to be sexual with multiple men was—and still is—seen as damaged goods by a misogynist society. But a man who sleeps with many women is seen as admirable.

Boys who lose their virginity are seen as transitioning into manhood. It’s a marker of mature masculinity to claim a woman’s sex. But for teenage boys who are ill-equipped for the emotional rollercoaster of dating and sex, or who—like me—find sex to be discomforting, there’s a social pressure to do the deed.

This was true for me as an awkward teen in 1999, for the boys in “American Pie,” and for young men today who are having less sex than they have in 30 years, according to several surveys assessed by Psychology Today. As we’ve moved away from sex being a marker of masculine maturity, a person’s sense of self no longer has to be tied to sex. Researchers lamented that young men in particular have sacrificed relational skills to the virtual world since the start of the Covid-19 pandemic. But I believe that true intimacy isn’t about having sex; it’s about understanding sex and the role I do or do not want it to play in my life. True intimacy is authenticity, which starts and ends with me.

The week before my prom, I was all set to take a lovely friend as my date when one of my soccer teammates asked if I would consummate the bet that night. I shirked off the question. Sex was the furthest thing from my mind. But word still got back to my date.

I woke up on prom day to a text from my date. She heard about the bet and was pissed. I didn’t blame her. The seniors got the whole day off from school, but my sophomore date still had to go to school.

In a panic, I drove to school to try to talk to her but her friends intercepted me. I ended up in tears in the guidance counselor’s office. I even cried to my soccer coach about how the stupid bet was now threatening one of my favorite friendships.

It was pathetic.

Humiliatingly, my soccer coach spoke to my date for me. I don’t know exactly what he said to her, but she agreed to go to prom with me. It was a mostly forgetful evening, and we both went home with other people.

Unlike the boys in “American Pie,” I gladly lost the bet. I’m not sure any of my former teammates even remember any of this, but for me it’s a deep trauma that I think about at least monthly.

Looking back on it now, having sex on prom night wouldn’t have changed me—at least not for the better. I went on to college and met my future wife, losing my virginity to her “as god intended,” though we didn’t wait until marriage. After I transitioned and found new virginities to lose, I realize now that none of it meant anything.

I didn’t “become a man” when I lost my virginity, partly because I was never a man to begin with. Sex also didn’t confer wisdom or maturity onto me the first time I did it. It didn’t devalue my partner the first time she did it, either. Body counts are fake, and we all care way too much about the social constructs we’ve put up around sex.

Like Jim in “American Pie,” I still hate sex and over the years, I have moved ever closer to identifying with the asexual label. Sex is a normal thing that most humans do, but it will not change you the first time you do it. In later “American Pie” movies, the boys at the center of the plot grow into men, and they carry their insecurities around sex into adulthood. Jim is just as awkward about sex in the second movie as he is in the first, and arguably even more awkward about it in the “American Reunion” movie that makes up the fourth and final installment of the “American Pie” franchise.

Losing my virginity did not have to be an R-rated bet. We’ve come a long way as a society, yet we still treat virginity as a marker of a woman’s value or a man’s manhood. Ultimately it’s just sex, and what really matters is that it happens on your own terms.

This piece was edited by Christine Grimaldi and copyedited by Tina Vasquez.