Is Prom the Best Night of High School? I Called My Date From 20 Years Ago to See What He Remembered

When I think back on my high school experience, there are a lot of memories to sift through—school spirit days and the spring musical (Pippin, clearly), hallway loitering and group projects, roller coaster friendships and gym class humiliations. But there’s no memory bigger in my mind than prom.

After all, it was the stuff of angsty teen movies, and while my small-town school in Massachusetts, with a graduating class of 97, wasn’t exactly a hotbed of romance (there were just two “official” relationships in my grade that I can recall), the entire event was still swimming with potential. I was eager for a night that fulfilled the fantasy: A dreamy date, a beautiful dress, a slow dance and maybe a not-so-chaste kiss.

For the record, it didn’t go exactly to plan. My date was decidedly in the friend category, though I had a crush on him for sure. My dress came from a dated bridal shop, rather than a trendy place like Nordstrom or Jessica McClintock. And as for the slow dances? They were, um, awkward. But still, in my mind the evening achieved magical status. I went to the prom in a long gown with a handsome boy, and somehow that was enough.

But 20 years on (and with prom season fast approaching) was the occasion really as epic as I remember it? Or was I assigning too much nostalgia to a night long over-hyped?

There was only one person I wanted to ask: My prom date, Matt, from 20 years ago.

But first I had to track him down. I tried Facebook first (no reply), then somehow dug up an old email address. I got an immediate response. He was now living in Malta with his wife and two kids, and he was more than down to reminisce.

“Did I ask you or did you ask me?,” I questioned.

“You asked me, but I remember there was another player involved—Carin maybe?” Matt said. Oh yes. Carin, my best friend at the time, wholeheartedly supported the idea that Matt and I go together. She unceremoniously dropped a hint about my interest in the hallway one afternoon as we changed classes, and he later approached me to seal the deal. I was over the moon.

Of course, this was a time before promposals and TikTok; you didn’t need a public presentation with high production value to land a date. You just needed a bit of nerve and cash for the tickets, which Matt and I split the cost of. “There wasn’t a ton of pressure on anyone,” Matt reflected. “In some cases, you didn’t find out who someone else was going to prom with until that night.”

From there, we rattled off our own memories of the evening: The theme was “Moondance,” a nod to the Van Morrison album, which became the evening’s signature song. There were corsages, a seated dinner and something called a promenade in front of a gazebo in a neighboring town, which was basically a pre-prom photo call for the entire community.

“I almost felt like a debutante,” Matt laughed.

Obviously, we got a limo. And we put a ton of work into our ensembles; I wound up with a slate gray off-the-shoulder number for $190, alterations included, and Matt rented a white tux, Tom Hanks-style.

He remembered stressing about the photo shoot at my house (“I begged my own parents not to come”) while I remembered the fear of expectation. Would Matt find me on the dance floor for every slow dance? (He did.) Would anyone get drunk? (Not until the after-party at my friend Steph’s house.) My hopes for the evening fell somewhere between “Donna Martin graduate” and Drew Barrymore’s Never Been Kissed.

But our biggest shared revelation was that prom felt like a dress rehearsal for real life. “Prom was when I actually felt like the entire ‘pretending to adult’ thing reached a peak,” Matt said. “It was a moment to shine and make an effort to establish ourselves when we weren’t really sure who we were trying to be. When we stepped out of our limo, we were more sparkly, but also more mature.”

Maybe this is why the evening—which in retrospect was really just a dance I attended with a friend—looms so large in my memory. I was quite literally putting a bow on my childhood while fumbling my way toward being a grownup. I was the star of my own coming-of-age film and that, in and of itself, made it magical.

I have to wonder if teenagers today can recreate that same sort of magic. There’s COVID-19, which has wreaked its own havoc on the experience. But there’s also so much more external pressure. The expectations of my time were Hollywood-derived; nowadays, social media sets the standard and simultaneously puts every moment, fantastic or fumbling, on display. That has to be hard.

Eventually, Matt’s daughter interrupted our call, but it was also the natural time to say our goodbyes. After we hung up, I was buoyed by how easy it had been to talk with him. A testament to our friendship? Perhaps. Or maybe it was our forever bond: The night we awkwardly swayed together to Van Morrison, the night we said goodbye to childhood.