The Saddest Prom Story of All Time

Too cool for words.

Yet another prom season has arrived. And, amazingly, I’ve never used this space to tell the saddest, most pathetic prom story of all time.

So, here I go …

The year was 1990. I was a senior at Mahopac High School. Gawky, awkward, never held a girl’s hand or—heaven forbid—kissed one. I wasn’t a popular kid in school, wasn’t an unpopular kid in school. I was, well, quirky. Sorta like I am now. I ran track, served as the newspaper’s sports editor, went by the nickname “Pearl,” had a best friend (Jonathan Powell—still very tight) who I pretty much did everything with. I was happy and content, but also very concerned. Prom, we’d all been told, was the most important night of our lives. It had to be great! Amazing! Remarkable! Spectacular!

I had no one to go with.

There was a girl on the track team, Laura Garraway, who was cute, but she had a boyfriend. My secret crush, Teresa McClure, barely knew I existed. I took Jody Cohen to my junior prom, but we were merely Hebrew school pals. Couldn’t go to that well again.

The first person I asked was Michele Sheehan. She was a sophomore, ran track with me. We barely knew one another, but she was pretty and friendly and Irish (I loooooved Irish girls). I figured out her schedule and, one afternoon, waited for her outside the library. When she emerged, I tapped her on the shoulder. “Uh, Michele …”

“Yes, Jeff.”

“So, I was wondering, whether, eh …” My hands were sweating. My heart was pounding. I was as smooth as tree bark. “Would you, maybe, go to the prom with me.”

Long, long, long silence. Ugly, horrible silence.

“Sure,” she said. “I just have to make sure it’s OK with my mom.”


Yes! Yes! Yes! Yes! Yes!

Two days later. “I’m sorry, Jeff,” Michele said. “My mom doesn’t know you, so she feels uncomfortable. I can’t go with you.”


There was now, if memory serves, about three weeks to go. Most everyone had a date. I was screwed. Super screwed. I couldn’t go alone. Couldn’t go with my mother. I looked around, and looked around. Then, I saw her: Christina Ruiz. Like Michele, she ran track. Like Michele, she was friendly and perky. We barely knew one another, and I suspected she was significantly too cool for me. But, hey, I didn’t have much of a choice.

Hence, after practice one day I approached. “So, Christina, I know this is sorta late, and kinda out of nowhere, but would you go to the prom with me?”

I expected no.



“Yes. Sure.”

I was stunned. Staggered. Elated. A girl—a real girl!—would go to the prom with me. So what if we were kinda strangers? So what if—for all I knew—she had a boyfriend and a father with a gun? I was going to the prom. I was legit.

The night, oddly, is sorta fuzzy. That whole “The prom is the biggest event of your life” narrative (repeatedly annually by thousands upon thousands of American parents) is nonsense. Well, not if you get pregnant, or murdered. But, otherwise, nonsense. I remember Christina looked stunning—blue dress, hair done all nice. I remember I looked like a string bean in a tuxedo—all elbows and shoulders. I bought her a corsage, headed to her house and awkwardly pinned it to her strap. We then drove to my friend Jeff Goldeberger’s home, where the limo awaited.

One of the parents (lord knows, not mine) slipped the driver $50 so we could bring along a cooler filled with booze. Everyone drank—except for me. Why? Because I was scared and sad and afraid. When we arrived at the Glen Island Casino in New Rochelle, the music was loud, the food mediocre, the night sorta forgettable. Because we were teenage boys, and teenage boys tend to be quite stupid, jokes were made about hooking up and “getting some.” I had no remote idea what this meant or entailed. I was just happy to be dancing with a pretty girl.

At night’s end, the three couples boarded the limo and headed back to Jeff’s house. This is where it all gets especially pathetic.

At some point, I decided this would be the night I finally kiss a girl. My plan was simple and relatively fail-proof. Upon reaching Jeff’s house, I’d say goodnight to the other couples and offer to drive Christina home. We’d arrive, I’d walk her to the front door, say something witty (“How about that Bruce Berenyi!”), pucker up and smooch. I didn’t need the kiss to be long, or passionate, or meaningful. I just needed a fucking kiss.

Well, we’re all in the limo, heading to Jeff’s. It’s, oh, 10:30 pm. The limo is under contract until 11:30. “You know what,” Jeff says, “once we get to my place, the limo can take the girls home. That seems to make sense, right?”

Everyone agreed. Even I, outwardly, agreed. Inside, however, I was screaming like a madman. What! What the fuck are you talking about, Goldberger! You’ve already kissed a fucking girl! For all I know, you’ve had sex. Dammit, dammit, dammit, dammit, dammit, dammit, dammit! Noooooooooo … noooooooo … nooooooo …

We arrived. I exited the limo. Christina said goodnight. The door closed. The long black vehicle faded into the night.

But wait!

I got in my ol Datsun 510 and sped to Christina’s house. Seriously, I did. I drove as fast as I possibly could. My plan was simple but, I must say, sorta John Cusack-holds-a-radio-above-his-head romantic. I would beat her to her house, call out her name as she exited the limo and say, “Christina, the night wouldn’t be complete without a kiss …” Or some jabber like that.

I got to her house. I sat, waiting. And sat waiting. And sat waiting. And sat waiting. And sat waiting.

The limo, clearly, had beaten me there. I lacked the guts to knock on her door, or call her the next day or, do, ahem, anything at all.

I simply returned home, and cried myself to sleep.

* The beautiful aftermath. Christina and I are now pals. And her fashion blog is awesome.