My First Kiss Broke the Rules

Call me a cheater, but I didn’t regret it one bit.

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Now, happy story time.

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I cheated on someone with my first kiss.

I didn’t realize it back then, when my tongue touched the slimy one of the blue-eyed boy in front of me. Eyes tightly shut, my tongue moving in a rotary motion, just as my friend Marta and I had practiced over and over, using our hands as proxy.

Our first kiss was one of the most talked-about topics at fourteen.

Marta and I would discuss it endlessly, and we would practice in front of the mirror: kissing our hands clenched into fists or even an apple, then giving each other feedback.

We learned everything we knew from movies, with Meet Joe Black and Pearl Harbor being our top two teachers. We even took mental notes when the eighteen-year-old boys at the church youth group described what we were supposed to do. We were determined to be prepared for that moment.

Throughout middle school, I had always been on the sidelines when it came to romantic attention. Little did I know, puberty and losing that extra baby weight got boys to look at me too when I started high school.

I wasn’t expecting anything at the time, so I was genuinely surprised when Ale asked me to be his girlfriend.

It happened during one of our school friend’s birthday parties with the entire class, six months into my first year of high school. We danced all evening to Hips Don’t Lie by Shakira, like it was the most exciting thing in the world—us growing up.

Then, just as I spotted my dad’s Toyota Galloper pulling into the parking lot to pick up me and some girlfriends, Ale posed the question.

“Do you want to be my girlfriend?”

I was caught off guard. Puzzled. I hadn’t seen it coming, and there wasn’t time to think. I didn’t want to be rude, so I said yes. I mean, I could finally say I had a boyfriend. We would hold hands, walk side by side, that would be exciting.

Except, as soon as I got into the car, I didn’t feel excited at all.

Ale sat in the desk in front of me. In Italy, teachers rotate classrooms, not the students, so where you sit the first day of school sets the tone for the entire year.

It’s the most important decision to make on day one, and that year was even more significant since we were just starting High school: a new class, a new set of friends, a blank slate.

Marta and I knew we’d sit next to each other, and got to school early to get the desk we wanted. We strategically picked the third desk of the four by the wall, not too close to the front or the back, not in the center, but visible enough for the teachers to have a good impression of us.

It was so easy for Ale and his desk mate to turn around and share a joke about the professors or pass a note here and there. He was really cute, a year older than us, and looked slightly more mature than the other boys in the class. That extra year gave him an edge.

Ale had gorgeous amber eyes, the kind you’d expect from the protagonist of a fantasy book, and a bright personality, but all our interactions until then had firmly placed him in the friend zone. No butterflies when I looked at him, just fun and comfort. And I liked that about our friendship.

“You know you’ll have to kiss him, right?”

Marta said four days into my new relationship. My stomach dropped, a wave of discomfort washing over me.

“With the tongue?” I asked, earning an incredulous look from my best friend.

“Yeah, that’s what it means to be boyfriend and girlfriend, right?”

Something felt off. If this was going to be my first kiss, I should have felt my heart race, right? But it wasn’t, at all. And that was all the confirmation I needed—I had to break up with him. But damn, it had only been four days!

I couldn’t let my first official relationship last less than a week.

Luckily, the annual week-long ski trip with my family and other families from the church during school break was coming up in a couple of days. It was the perfect excuse to buy myself more time.

Coward.

And then, when I got back, I could let Ale know that “friends” was the right label for our relationship. That seemed like a solid plan.

For the next two days, I stuck close to Marta, strategically positioning myself in groups, and made sure the moments when Ale and I were alone were few and brief. Thankfully, I managed to get away with only a quick, closed-lips kiss on the mouth.

I grew up in a small suburb of Milan, where families knew each other, so I was familiar with about 90% of the people coming on the trip. Marta and her family weren’t coming that year, which meant I had to make decisions on my own, at a time when fourteen-year-olds didn’t have phones.

“This is my childhood best friend, Jacopo,” Giulia, one of my middle school friends, introduced him. I awkwardly shook hands with her blue-eyed friend, eyes the brightest blue I’d ever seen. He was slightly taller than me, with a hint of a baby beard, and the blue knitted sweater and wool hat he was wearing made him extra cute.

“Hi,” he gave me a bright smile, melting me away.

At that time, white teeth were in my top three most important hotness attributes. His hand was a little sweaty, or maybe it was mine.

Unexpectedly, there it was—that unpredictable flip in my stomach. And just like that, I knew I had a massive crush on the new boy on the trip.

It helped that I was friends with Giulia, so it wasn’t hard to spend time with Jacopo since he mostly stuck by her side, being the newcomer. I was open and chatty, trying to join in on mischievous activities, and I even went skiing with them a couple of times, ditching my dad.

Being close to Jacopo and part of the inner circle was enough for me, as I gave him secret glances with sparkly eyes, convinced I was hiding it well.

The truth was, I definitely had a stupid smile on my face when Giulia confronted me.

“Do you like Jacopo?” I froze. “I think he likes you back,” she added, with a hint of annoyance.

I denied it as best as I could. “Me? Pfff, no way.”

But then, one evening five days into the skip trip, right before the whole group sat down for dinner, Jacopo asked me if I wanted to go with him to the basement, where all the board games were stored.

I said yes.

A moment alone with him sounded perfect. And right when we got out of the elevator, he turned toward me and, out of nowhere, asked the question.

“Can I kiss you?”

What just happened? The sky was falling, the ocean was raging, my stomach was overflowing with butterflies, and my heart was pounding like crazy.

I nodded, no hesitation.

I closed my eyes tightly, waiting to feel his lips on mine. This was the moment I had practiced for countless hours—dozens of apples, washed hands, afternoons spent replaying the best kiss movie scenes over and over.

The milestone I would never forget.

The kiss was wet. Awkward, my tongue feeling robotic as I tried to follow all the rules I’d rehearsed in my head. His mouth felt different from my stiff hand, moving with a life of its own. His lips enveloping mine. I didn’t know what to do with my arms, so I just kept them stiff at my sides. I could not tell if that was his first kiss too.

I opened my eyes slightly to check in and saw that his were wide open. Okay. He was breaking fundamental rule one, but it did not matter. We kissed for maybe four or five seconds, which felt both long and short. Infinity.

When we broke apart, I braced myself for regret. But it didn’t come. I was all in.

“Let’s take this game upstairs,” he smiled picking up Taboo. And just like that, we left. No words said, no clarification needed.

That was my first and last kiss with Jacopo.

I wanted to see him again, I was head over heels. He wasn’t just cute; he was funny, adventurous, and a bit smug, all traits my younger self was drawn to. But afterwards, I found out that the “naughty boy” of the group had made fun of him for kissing me. Apparently, I wasn’t the most “appetizing” girl out there.

That stung, but at the same time, I felt a strange sense of happiness.

Happy that my first kiss had been with someone who made my stomach flutter, even if he didn’t feel the same way.

To be fair, I never heard his side of the story, so I don’t know what really happened. What I did know is that he smiled brightly at me before and after that kiss, which was enough of an indication that he wasn’t a complete fraud.

On the contrary, I was the fraud, happy that my first kiss hadn’t been with my actual boyfriend.

The following Monday morning, back in class, I leaned over to Marta. “I kissed someone for the first time,” I whispered.

“What?! How was it? I want details,” she snapped back.

We spent the next six hours quietly chatting through class, dissecting every little thing that had made that moment what it was, including the ghosting afterward.

I felt a sense of maturity washing over me, and with that newfound confidence, I also found the courage to break up with Ale.

We both agreed we had liked our relationship better when we were just friends, so the breakup wasn’t heartbreaking. Still, we stopped exchanging letters and the jokes in class became less and less frequent as he shifted his attention to other girls.

“Wow, your first kiss was cheating,” Marta had said right after my breakup.

I remember those words to this day. I didn’t mean for that to happen. Did that make me a bad person? Is someone who follows their heart fundamentally selfish and bad?

I saw Jacopo the year after at the same ski trip. We were fifteen by then, and his newfound attitude made him ignore me almost completely as he joined forces with the “naughty boy” of the group.

Was I upset? Maybe a little. I couldn’t deny I wanted that validation again.

I wanted a second kiss.

But by then, I’d already planted the seed with someone else at school, who soon after became my first real boyfriend, my first love, and eventually, my heart-shuttering breakup.

Marta and I had a heart-to-heart last year, twenty-two years after these events, after she put to sleep her three years old daughter. She told me she didn’t even remember the cheating part, or the tale of my first kiss. I confessed I didn’t remember hers either.

We laughed, and then cried, thinking back to those simple times, reliving the dreams of two fourteen-year-old girls who just wanted the most perfect first kiss.

With love,

Simona

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And what about you? Do you remember your first kiss? Let me know in the comments!