1995, Halifax, Nova Scotia, Canada

By Ryan Murphy

More Americans lose their virginity on prom night than any other night in their lives. That’s a fact. And while I might not be American, I was counting heavily on the power of statistics when I graduated from high school in June of 1995.

My prom date was Rebecca Grossman, a girl I had known for three years and had developed a crush on in the past three weeks. Rebecca and I had been in a number of theater productions together since our freshman year, at first toiling behind the scenes and only later in front of the footlights. We shared a passion for drama, alternative music, and as I would discover only years later, women. Rebecca wasn’t exactly a man-hating lesbian, but she did have a deeper appreciation for Melissa Etheridge than most women in our graduating class.

It’s just as well that I didn’t know about Rebecca’s sexual identity, since most of what I knew about lesbians at the time was limited to what I had learned from watching porn films. I knew they were gorgeous, I knew they were sexually wanton, and I knew that they lived in sororities and occasionally got sent to all-women’s prisons. In other words, I knew nothing.

Rebecca and I went to the prom with my best friend Spencer Murray and his date Jennifer Simpson. Spencer and I had both lusted after Jennifer over the years, but had always been rebuked. She wasn’t especially beautiful, but she did seem somehow above it all. Unlike most of the school’s jocks and wannabes, Jennifer was clearly never going to look back at high school as being “the best years of her life.” That sophistication, and the fact that she was unattainable, drove us wild.

Spencer had asked Jennifer out three times that year and been flatly denied on each occasion. The fact that she agreed to go to the prom with him seemed like something of a miracle, and it was an opportunity that Spencer wasn’t about to waste. Unfortunately, it wasn’t completely up to him.

Jennifer began the evening of our prom by announcing that she had a terrible headache. She apologized profusely (too much, upon reflection), and kept to herself for most of the meal. When the dancing began she politely stayed off to the side, disappearing almost entirely for most of the night.

Spencer tried to stay upbeat, but the evening clearly wasn’t progressing as he thought it would. Let’s face it, if you can’t get booty when you’re wearing a tuxedo, there isn’t much hope for you at all. With each passing minute, Spencer saw his window of opportunity closing. To his credit he didn’t panic, equipped with the knowledge that the prom would continue into the wee hours of the morning.

Following the dance we all went to a beach a half hour away. Spencer and I piled into a car belonging to our friend Darren, while Jennifer and Rebecca piled into a second vehicle. We agreed to meet each other in an hour after we had had time to change and freshen up. The entire ride down we discussed our prospects. Spencer was upset that dinner hadn’t been smoother, but was still optimistic. Ever the gentleman (but mostly just desperate to get laid), he even brought along some aspirin to ease Jennifer’s headache.

I was also upbeat. Rebecca hadn’t responded much to my advances at dinner, and she had spent most of the evening slow dancing with a woman with a crew cut, but I was reasonably certain she was just playing hard to get. Ever the gentleman (and definitely desperate to get laid), I brought along 12 condoms. Clearly, I understood as little about sex as I did about lesbians.

Regardless of what we did or didn’t know, we felt confident that a moonlit beach would be the ultimate aphrodisiac. It was a late June evening, the air was cool, and the wind was ripping across the ocean with a strength of purpose I only wish I had when approaching women. Roaring bonfires had been lit across the beach and people were passing joints and passing out in equal numbers.

We walked amongst them, looking around for our dates for nearly half an hour. We found hordes of drunken teens and several of our classmates having sex in the bushes, but we didn’t find our dates. No one had seen them, and with the partying well under way, no one seemed much to care.

Needing desperately to warm ourselves up, Spencer and I decided to return to Darren’s car. Given enough time, we reasoned that Rebecca and Jennifer would probably find us. The moment we got within 50 feet of Darren’s Lincoln Town Car, we noticed it was bouncing up and down. We had all agreed on the drive down that “if the car’s a-rockin’ don’t come a knockin’.” But we never said a thing about not peeking.

Frankly we couldn’t believe that Darren was losing his virginity before we were. We’re talking about a guy whose last meaningful experience with a woman was breastfeeding, but if it had to be anyone, we were glad it was him. If nothing else, it would finally give the calluses on his hands a chance to heal.

Spencer and I approached the back passenger’s side window and looked in. What we saw wasn’t Darren, but the lily-white ass of Anthony Grant pumping away. Beneath him was Jennifer Simpson. Her eyes were sealed shut and she was moaning heavily.

Spencer was devastated. What really hurt wasn’t that Anthony and Spencer were bitter rivals, it was that Anthony hadn’t even worn a tux to the prom. He had gone in his father’s rumpled suit. In our opinion, guys like that didn’t deserve to get laid.

Spencer backed away, completely dejected. I tried to console him, but he was beyond words, so instead I consoled myself by staring into the car for a while longer. Even then I knew the value of a free sex show.

Frustrated, but also still cold, Spencer opened up Darren’s trunk, fished out a couple beers, and then crawled in, warming himself up as best he could. Feeling foolish standing alone, I joined Spencer and lay down beside him as Anthony and Jennifer made the car bounce and sway like a perverted merry-go-round. We both just lay there bouncing up and down. I think Spencer may have begun to sob, but I can’t be sure.

It was at that point that Darren, bounding into the beach parking lot, saw us. He gave us a big wave and began jogging towards us … then running … then sprinting. Still five feet away Darren dove headfirst into the trunk. The force of Darren’s impact – and his wildly flailing legs - caused the trunk to slam shut.

For a moment everything was perfectly quiet. We couldn’t hear the waves breaking on the shore, the wind was barely whistling, and the moaning had ceased in the backseat. That’s when the yelling began. Spencer started to savagely rip into Darren, unleashing all of his pent-up frustration. I’m convinced he would have beaten him too, but the fact of the matter is we were packed in tighter than gay sardines.

After five minutes the backdoors of the car opened and Anthony and Jennifer walked away. We screamed for help, but they didn’t respond to any of our entreaties. And so we waited. Seconds turned into minutes, and minutes turned into hours. We passed the time alternating between berating Darren and consoling Spencer. When we got tired of that we screamed for help. From Fast Times at Ridgemont High to Dazed and Confused, no high school movie we had ever seen had prepared us for a moment like this.

By now, we had been in Darren’s trunk for an excruciating three hours. Darren kept on reminding us of how much warmer it was in the trunk then on the beach, but that was hardly any consolation. The last time someone spent that much time in a trunk they ended up facedown in the Hudson River. The entire time I was playing out the same conversation in my head:

1st Student: “So how was your prom night?”

2nd Student: “It was awesome, I got totally baked and ended up having a threesome with a pair of cheerleaders.”

1st Student: “Twins?”

2nd Student: “You bet!”

1st Student: “That rocks!”

2nd Student: How about you?

1st Student: A bunch of us got naked and streaked the principal’s house!”

2nd Student: “Right on! What did you do, Ryan?”

Me: “I spent the night in a trunk with two other sweaty guys.”

2nd Student: “Good times.”

1st Student: “Good times.”

We finally got rescued just after the three hour and 20 minute mark. Our savior was Jim-Jim, a 23-year-old who had just wrapped up his 8th, but certainly not final year of high school football. Jim-Jim had evidentially heard our girlish cries and popped open the trunk to investigate. What he found were Spencer and I staring back up at him and Darren flat on his chest with his ass perched high in the air.

Jim-Jim didn’t bother asking any questions. He knew better than that. Instead, he took Darren by the ankles and ripped him out of the trunk, nearly robbing him of his manhood in the process. Spencer and I crawled out, shook Jim-Jim’s hand, and then took turns beating Darren.

It was now 7:00 a.m. Not only had we not lost our virginity, but I had spent the better part of my prom night with my face wedged in another man’s armpit.

For years after I wondered what had ever become of Rebecca Grossman. We had failed to stay in touch and reports about her back home were sparing. It wasn’t until six years later, in the fall of 2001, that I saw her again. This time the setting was Montreal, and I hadn’t been locked in a trunk for a good six months.

Rebecca was doing her masters at Concordia University and was living two houses down the street from her own apartment. It was pure serendipity. She had spent the past few years, I discovered, going to college in New Brunswick. I also discovered that she had completely abandoned any interest in lesbianism.

We went out for coffee, re-hashed old times, and discussed mutual friends. Before long, one thing led to another and we ended up in her apartment making out on her couch. She wasn’t a good kisser, but that was hardly the point. Our make-out session was far more about unfinished business than it was about losing ourselves in the here and now.

Rebecca and I remained friends but we never kissed again. We didn’t have to. The circle had already been completed. It may have taken me longer than most to have closed the chapter on high school, but I did it on my own terms. I sealed it with a kiss.

Was high school the best time of my life? No. But at least now – 10 years later – I can say it’s finally over. If only Jim-Jim were so lucky.

Ryan Murphy has written for HBO, A&E, Walt Disney Studios, Fox Sports, and many others. He presently lives in Vancouver, British Columbia, where he tries his best to limit his daily intake of Starbucks and fleece.

Posted by Elizabeth Armstrong Moore on Wednesday, March 21st, 2007 | Email This Post

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