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My First Kiss: The Messy Complexity of Sexual Milestones
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“I felt anger for months after allowing my first kiss to be this weird, uncomfortable, not-at-all-magical experience.”
In this op-ed, Condé Nast senior research manager Yulia Khabinsky reflects on her first kiss, and the loss we experience when expectations don't match reality.
When I was young, I imagined my first kiss would happen haphazardly with a boy I had a crush on. Maybe we would be alone on a corner of the blacktop during recess and he would lean over and give me a peck on the lips. I'd run and tell all of my girlfriends, and they'd tease me and I'd blush, feeling a bit embarrassed — but just a bit. Mostly I'd feel satisfied and adult-like.
After I entered middle school, I was certain it would happen during a coed sleepover, late at night, while playing spin the bottle. I wasn't sure which one of us would spin, but it didn't really matter; the bottle would slow cinematically, point toward the other, and we'd each lean forward and kiss, awkwardly but sweetly.
In high school, I imagined a made-up boy cupping his hands around my face, gently pulling me in. You know, the kind of kiss they zoom in on in teen movies. The kind that's totally, utterly unrealistic.
But my first kiss didn't happen on the playground, or during a middle school game of spin the bottle, or in high school with a boy who cupped my cheeks. It happened when I was 15, in a hotel room two hours from home, with a 19-year-old boy I felt no sexual attraction to.
So much of how we measure adulthood is centered on achieving specific milestones, like getting a driver's license, a first job, graduating. A first kiss, a boyfriend (or girlfriend), and losing your virginity rank high among these milestones. Sometimes, even more than those other goalposts, sexual milestones can feel like the true markers of growing up. If they are delayed or never happen, we may feel like there's something wrong with us. I know I did.
When my first kiss finally did happen, it was icky and not even something I wanted, which made me feel much worse.
First kisses are supposed to be memorable and a bit clumsy — a careful eschewing of childhood innocence. Mine was, well... I don't actually remember the details. I just know that we did kiss at some point, because the hookup that followed also ticked off a few other firsts, though we stopped short of sex.
But this isn't a story about a boy taking advantage. Not really. The boy in question was fine; nice enough, I guess. This is a story about letting go of the shame we feel when things happen that we don't want to happen, and when expectations don't match reality.
During my junior year of high school, a friend invited me to stay with her in a hotel suite in a city a few hours away. She was looking at colleges in the area and wanted to visit a guy friend who was a freshman at one of the schools she was interested in.
After hitting up a few dorm parties, my friend and I left for the hotel. The guy friend and his buddy tagged along. The four of us spent a few more hours hanging out on the hotel room's balcony. We drank a bit, but no one got sloppy. We mostly discussed books that inspired and changed us, and the guy friend spoke excitedly about a philosophy seminar focused entirely on the work of Czech author Bohumil Hrabal. At one point it felt as though I was observing myself from afar, amused by how mature and highbrow it all seemed. So much more of this to look forward to, I thought. I couldn't wait.
Soon I saw the guy friend look over at his buddy and cock his head slightly toward me. It was the tiniest movement, but I understood precisely what it meant. It relayed, "Do you want to hook up with her?" Technically, I knew I had a say in the matter, that I could've told him I wasn't interested, that I could've just rejected his mild advances and he would've gone home. In that moment, though, it didn't feel like a choice; instead, it felt like a done deal. 
My friend very much wanted to hook up with the guy she'd come to see. At one point she came over to me and asked in a whisper, "You've kissed someone before, right?" I lied: "Yes." I had imagined myself saying no plenty of times, in scenarios where I was feeling forcefully coerced, or if someone I didn't know was coming onto me. But the come-ons I envisioned were always so overt. I never mentally prepared myself for saying no in a situation like this, where I felt as though I was among new friends — it just seemed more "polite" to say yes.
So I said yes, and had an encounter with a boy I really knew nothing about, except for his name. I'm sure he thought I was 17, since that's how old my friend was. But I had skipped a grade and had a late-spring birthday, so being only 15 was a starker contrast to his 19.
There were a few moments when he gently guided my hand where I didn't really want it to be guided, but he stopped when I stopped and didn't pressure me to move forward. He left early in the morning. Something about having to study for a test. A generic, unbelievable excuse for a Sunday at 6 a.m. I guess I did get my cliched, cinematic experience in the end because I remember walking him out, and it was raining. To this day I can picture his raincoat better than any feature of his face.
I was angry with myself for months after, for the agency I gave up that night; for allowing my first kiss to be a weird, uncomfortable, not-at-all-magical experience. It felt as though the milestone was something I was meant to protect, and I had failed. I let the specialness of the moment get stolen from me.
I never again kissed a boy I didn't want to kiss. I've learned, though, that not all moments can be qualified simply as good or bad. Some moments just happen, and you learn from them. Or you don't. And that's okay too. Much of what we build up in our heads doesn't transpire the way we envisioned. Not everything we live can be assigned a moral designation. That night eventually took on a more transcendental quality, especially the precursor to the kiss: I bought the Bohumil Hrabal book we all discussed and it became a prized possession.
Sexual experiences, especially, are fraught, complex things. Our self-esteem, maturity, curiosity, our identity — it's all tied up in these experiences. We want them to play out a certain way, but if they don't, we feel like we've gone off course somehow.
But life doesn't follow a prewritten script. And self-compassion may be one of the most important skills we can learn. It took me awhile to give myself grace. Now if you want to hear the story of my first kiss, I no longer mind telling it.
The young person’s guide to conquering (and saving) the world. Teen Vogue covers the latest in celebrity news, politics, fashion, beauty, wellness, lifestyle, and entertainment.
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