A Really Hot Guy You'll Never See Again

At 14, the boys at my school weren't asking me out. So I met up with a boy from the Internet.

This is a true story about my teenage years. Normally, something like this would be paid (and in the future I’ll be releasing more personal essays for paid subscribers.) However, I’m making this one free, as appreciation for all the new free subscribers over the past month. Thank you from the bottom of my heart! Ultimately, I try to balance my free and paid content so everyone feels they’re getting a good deal. Please subscribe however you want, to see more!

It was spring 2004. George W. Bush was running his reelection campaign against John Kerry. Newspapers frequently reported gruesome updates from the Iraq War. But most importantly: I, 14-year-old CHH, was hopelessly single.

Although I had better luck dating boys than making platonic female friends (my missed social cues didn’t seem to register as much with boys) I still felt like I was struggling. I had one close female friend, a former Unitarian and newly converted Druid named Rachel. I had a boyfriend earlier in my freshman year—Tony, a sixteen-year-old thespian, who plucked me from the first week of school and absorbed me into his friend group full of cool older kids who “did pot” and knew who David Mamet was. Tony broke up with me two months later (the reason he gave was that he was too stressed to have a girlfriend because his cousin was on death row for killing a cop—although I’m sure it was a coverup for just not being that into me, it somehow was also a true story.)

I didn’t take the breakup well. Not only did I bore the crap out of everyone I knew with stories about how stupid Tony looked in his Hawaiian shirt at the slam poetry club show, but when Tony got a new girlfriend who looked suspiciously like an older version of me, I became obsessed with the idea that she was actually a twenty-something narc planted by the feds to get kids expelled for drug possession. Given that drug-related expulsions skyrocketed that year, I had some kind of basis for this theory, but I’m not sure what purpose it served for me to hide out in an empty short bus and take photos of her from afar with my Kodak FunSaver camera.

Tony himself was expelled for marijuana use around this time (Trust the plan! The Storm is coming!) and without Tony to obsess over, I felt empty and lonely. Because he had scooped me up at the beginning of orientation, I never had a good chance to bond with kids my own age—and it’s safe to say that even if I had, I would have alienated them anyway. To add insult to injury, Rachel got a boyfriend, and wouldn’t stop talking about how they did “dry oral” on the lacrosse field (she clarified he licked her over the underpants, while she was also wearing a maxi-pad.)

I needed to find a boyfriend so I could catch up with Rachel, who in my eyes was engaging in some of the most sophisticated grownup behavior imaginable. But it was hard to accomplish this when all the boys at school seemed so inaccessible. Most boys in my grade didn’t even seem interested in girls—they were baby faced and squeaky-voiced, still lurking in the shadows of school dances, terrified to make eye contact, listening to Weird Al together on their Walkmans. I might have been interested if any of them showed interest in me, but none did, and I hated the idea of making the first move. The only boys who seemed like they actually liked girls were the hot popular boys (all five of them), and they never would have glanced in my direction. Besides, it’s not like we would have anything in common—I didn’t have anything interesting to say about sports or Motorola flip phone ringtones.

I wound up venting to Ariel, a friend of mine from theater camp, who went to public school a few towns away. She had the perfect idea: I needed to expand my horizons. There weren’t a lot of eligible boys at my school, or at least that was how it felt. But my school was just one place, and an admittedly tiny school at that, with a skewed gender ratio.

“There are two guys I’m thinking of,” she typed one day on AIM. “One of them I think might be gay because his catch phrase is vaginas are gross. The other one is kind of cute.”

I made the decision to go with “kind of cute guy” instead of “guy who openly hates vaginas,” who would almost certainly not be amenable to dry oral. My friend gave me his AIM username. His real name was Zach.

We started talking, and I couldn’t help but wonder what he looked like. We didn’t have any form of social media, not even MySpace. Sending photos of each other was cumbersome and involved digital cameras, various wires, and lengthy uploads. Ariel had sent me a photo of Zach, but it was a yearbook photo via her dad’s fax machine, which didn’t translate into anything resembling a face. All I knew was that he had “tan skin, dark hair and green eyes.” But I wasn’t going to push the issue. I didn’t require boys to be that handsome, especially if they were fun to talk to.

And Zach was fun to talk to! He messaged me first so I didn’t have to make the first move. He asked me questions about my life, and he actually seemed to enjoy my dumb stories about pranks I played with my younger brother, like staging absurd arguments in front of our parents to see who they’d side with. Zach was funny and chatty. I didn’t have to pull conversation out of him the way I did with other boys—our AIM chats were nicely balanced, as opposed to seven long chat bubbles from me and one “cool” from him. His jokes were all a bit American Pie-ish, but that was okay. He was fourteen, just like me, so these jokes were exactly my sense of humor. On April 20, he messaged me, “Happy 420!” which led to me scrambling to Google what that meant, coming to the realization that it was Hitler’s birthday. Zach was Jewish, so I figured he might have been reclaiming such a day as an act of resistance.

Zach was charismatic in the way boys at my school weren’t. He didn’t talk endlessly about how busy he was with algebra, and he was openly flirtatious. He asked me what kind of clothes I liked to wear, and remarked that he “liked when girls dressed up.” I didn’t feel like I had to steer things in a flirtatious direction. We didn’t have to pretend to be friends; we knew we had been set up for a romantic connection and acted accordingly.

One day, he asked me the question I knew was coming: what do you look like?

I gulped. I knew I wasn’t hideous, but like most fourteen-year-old girls, I didn’t consider myself that pretty. I was coming out of my awkward phase, and was finally growing into nose and chin, both of which were accentuated with unmanageable amounts of sebum which tea tree oil strips from Bath and Body Works were barely keeping at bay. My mom had finally started letting me pluck my unibrow, which, combined with my relatively under-developed body, made me look like a small Albanian man. And I finally had braces, which sounds awkward, but it was a lot better than what I had before—only four visible teeth on my top row of gums, like an eighteen-month-old baby. I was skinny, but I feared it was in the gangly Olive Oyl way and not in the Victoria’s Secret model way. And then there was my biggest insecurity of all—the fact that I barely filled out a 32B bra. Rachel, who had much bigger boobs, frequently complained to me about how she looked “too sexy” in everything she wore. She would joke that we should “trade.” I rolled my eyes. Sure, Rachel, trade with the girl who looks like Squidward in drag.

I’ve painted a pretty unflattering picture of my looks, but rest assured most people would have considered me a normal, somewhat cute kid. Unlike the stereotype of a socially awkward neurodivergent girl, I loved fashion and took pride in my appearance. I washed my hair every day with a shampoo that smelled like birthday cake. I had a wardrobe full of pink plaid and dark brown ribbon—to put it into 2024 terms, I was serving Y2K coquette office siren realness. I wore kitten heels to school every day, and never missed an opportunity to get dressed up. I knew I was far from a perfect 10, but I couldn’t have possibly been a bridge troll either.

But the point was, Zach asked for a photo and I didn’t like how I looked in photos. Every time my mom took a photo of me at a family gathering, I resembled a barnyard goat wearing a wispy brown wig. Every time I had to take a yearbook photo, I always opted for the re-do. If Zach saw a photo of me, surely he would lose interest immediately. A photo would bring me down at least two points on the hypothetical 1-10 scale. I’d go from a 6 to a 4! But he insisted. So I carefully located a Polaroid photo I took with my cousin at a beach side restaurant the previous summer. It was back when my hair was longer—since then, I had cut it from waist-length to shoulder. I was also tanner in the photo. But I wasn’t wearing much makeup, so the picture couldn’t be that deceptive. I dutifully scanned it, saved it, cropped out my prettier cousin, and uploaded it into our chat, which took approximately eighteen minutes.

Zach responded. Wow, you’re so fucking hot.

Hot? That wasn’t a word I associated with myself. My parents’ friends were clear about my looks: I was interesting. I was “dark featured” and “unique-looking.” I was an “intellectual man’s beauty.” I was the kind of girl that would finally be appreciated in college, once boys “grew out of chasing the blonde bimbos with big boobs.” It all felt so backhanded, and I wasn’t sure what they even meant.

I was riding high on Zach’s assertion that I, the awkward and pallid teenager with a face that was both oily and flaking, who still secretly played with American Girl Dolls and Calico Critters, was “hot.” That word felt reserved for bronzed coeds in frayed denim short-shorts and white tank tops, with highlighted blonde hair and names like “Becky” or “Jenna.” My heart aflutter, I asked him to return the favor and send a photo of himself.

“Oh, I can’t,” he said. “My digital camera is broken.”

“Do you have any Polaroids you can scan?”

“No.”

At this point, I might have suspected that I was being catfished, but that wasn’t something we thought about in 2004. Having a broken digital camera and no nearby Polaroids didn’t seem out of the ordinary. Besides, I had it on Ariel’s authority that Zach was a real person. I don’t remember the specifics of this part, but I believe my mom had verified Zach’s existence with Ariel’s mom at one point.

Now that Zach knew what I looked like, the conversation shifted. Out of nowhere, he asked, “I have a serious question for you and you have to answer it. Do you promise you will?”

“Sure,” I said.

“First of all, are you a virgin?”

“Yes.”

“Good, so am I. Although I did get a blowjob at camp.”

“Oh. Okay.” I hoped he wouldn’t expect that of me. If only there was some way to do dry oral on boys.

“Anyway, just imagine you were having the best sex of your life. I know you haven’t had sex before, but just imagine it.”

“I’ve never even masturbated before, I have no idea what that would be like.” I was, of course, lying about the masturbation thing. I was under the impression that only boys did that. Well, boys and me, and then one weird girl from theater camp named Melissa whose parents sent her excessive gift baskets. I would take my shameful masturbation habit to the grave, that was for sure.

“Just pretend,” Zach typed. “Anyway, imagine that you don’t know if the other person is a man or a horse. And like I said, best sex of your life. Do you keep going?”

I didn’t know what to say. How I really felt was irrelevant, it was all about getting Zach to like me. If I said yes, he might think I was a slut. But if I said no, he might think I was no fun. I settled on a noncommittal answer: “I would feel around for hooves.”

“No, it has to be a yes or no.”

“I guess I’d keep going,” I said, hoping I picked the right answer.

“Oh my God, I can’t believe you’d do that! You’re a freak! In a good way.”

Did I pass? I didn’t know. But more questions came up—would-you-rather type questions, the kind pulled from raunchy OkCupid quizzes (OkCupid wasn’t always exclusively a dating site- it used to be a hub for bored teenagers to take various personality quizzes, especially the “Slut Test” and the “Gay Test”, along with a quiz where you could rank other test-takers to guess which of them were the gayest and sluttiest.) I would giggle as we typed back and forth, occasionally looking over my shoulder to make sure my parents weren’t lurking. The only computer we had with working Internet was in our kitchen, so I had to be careful to minimize my chat window if Zach was saying something naughty.

As silly as it sounds, I really enjoyed talking to Zach. For a few weeks, we talked every single day. Never about anything too deep or serious, but the types of goofy PG-13 conversations that would have appeared in a straight to video Tom Green movie. At one point he asked me what my bra size was. Normally, this wasn’t a question I would answer but it felt tame in comparison to the horse sex thing. So I told him. I saw he was typing, then pausing, then typing again. Finally he said, “Small ones can be good too.”

Finally, he asked me to meet him in person. I was scared. He liked my appearance, but it was based off a photo. Surely, I couldn’t look that different from last summer, but what if the long hair and the tan were the things he liked? It was already clear he wasn’t too jazzed about my small boobs. And what if our banter online didn’t transfer to real life?

We agreed to meet at a mall nearby. There was something I found so exciting about getting ready for a date. This felt like a grown-up date, not the kind of casual meetup I might have at the dining hall or library with a boy from my school. I could get ready, emulating the graceful, cosmopolitan twenty-somethings I read about in magazines. I could put on a blouse and perfume and even lingerie (yes, I wore my “sexiest underwear” to meet up with this guy at a mall diner at 11 AM, after being driven there by my mother.) I felt sophisticated and cool as I leafed through my dogeared pages of Glamour Magazine to find the perfect “daytime smokey eye.” I still remember what outfit I settled on- a burgundy V-neck top with ruching at the bust, over the only push-up bra I had, a pair of low-rise flare jeans and block heel boots.

As excited as I had been getting ready, I suddenly felt a pit in my stomach as I sat on the bench outside the mall diner, waiting for him to come up the escalator, taking deep breaths through my nose, inhaling a symphony of Auntie Anne’s pretzels and Dippin Dots. I suddenly didn’t want to be there anymore. My mouth felt dry, I felt nauseous, I wanted to go home. I wasn’t sure why—I genuinely liked talking to him and was excited to see him. I suppose a part of me was scared that our raunchy jokes online would transfer to some kind of expectation that I be sexually adventurous in real life. I loved the idea of being grown up, being desired, being hot. But I didn’t want to actually do anything about it. As much as I wanted to catch up with Rachel, I didn’t really want to when I really thought about it. It was all a bit scary and disgusting.

I examined every teenage boy who came up the escalator. When the boy was especially cute, I hoped it was him. But when Zach finally showed up, I instantly knew who he was. Even though the faxed yearbook photo was blurry, it was clear enough for me to vaguely recognize him. He had a narrow, small face, large rounded eyes spaced close together, and straight, shaggy dark hair. What I wasn’t expecting, however, was that he looked incredibly young. He was short, and I was okay with that (Tony had been 5’4” or so) but Zach was more like 5’1”. He wore a too-big knitted beanie and an olive green GAP logo hoodie with his hands sheepishly scrunched in the front pocket. Then I saw something that horrified me—he was wearing the same GAP Kids cargo pants as my nine-year-old brother—the ones with zippers at the knee so they could be converted into shorts. I was wearing a pushup bra and vanilla lavender perfume on a date with a guy wearing children’s cargo pants.

We sat and ordered our food. He didn’t seem remotely happy to be there.

“So what are your thoughts on the election?” I asked.

“Fuck Bush,” he said.

“Yeah, same. Ha.”

It felt like we ate in silence almost the entire time. Where were all the funny would-you-rathers? The links to Quizilla quizzes titled “How Perverted Are You?” He hadn’t been afraid to be flirty and cheeky on AIM. At the diner, he had the disposition of a guy waiting for a bus after a long day at work.

After what felt like forever, we got the check. “We’re splitting it, right?” he asked. I nodded. My parents had given me $20, which would cover my stupid quesadilla and unsweetened Lipton iced tea.

“My mom is here to get me,” he said. “I should go. Nice seeing you.”

“IM me, okay?” I asked.

“For sure.”

I wasn’t sure what I had done wrong. When I got home, I knew I wasn’t going to get a message from him right away. And I was right—it took a day or two before I heard from him. But when I did, my heart raced. To hear the unmistakable “ding” of an IM and have it be from his username and not Rachel or some kid from my chemistry class asking what the homework was, or worse yet, one of those horrible chain IMs that I’d have to send to seven people.

Something changed about Zach since we met in person. He continued the hypothetical sexual questions on AIM, but they felt a bit more like an interrogation. He asked me how many boys I had made out with, the furthest I had ever gone with anyone, how far I would go with the next person. It just wasn’t fun for me anymore, and I missed when he was fun. On the bright side, he asked me on a second date, to go see the movie Troy in theaters. I still felt a bit nervous—he clearly wasn’t thrilled with our first date. But he was interested enough not to ghost me, so that was something.

Then one day he asked me, “Imagine you were on a cruise ship with your parents. What if you met a guy on the ship—a really hot guy you’d never see again—and he wanted a blowjob. Would you do it?”

I once again felt compelled to hack this question to come up with the perfect answer to keep his interest—not slutty, not frigid. The answer, realistically, was no. But I knew he didn’t want to hear that.

“Why wouldn’t I see him again?” I asked.

“Let’s say he goes to another school or something.”

“Okay, but if I liked him a lot I would want to figure out a way for us to be boyfriend and girlfriend not just give him a blowjob on a boat.”

“But let’s say that wasn’t possible, you’ll never see him again. Isn’t that better because nobody would find out?”

“I don’t know. Sure, I guess I would.”

“Okay, so when we go to the movies would you do that for me?”

Despite all the naughty backs-and-forths, I never expected Zach to directly proposition me for sex on AIM. He might have asked me what I was wearing, or asked me what I found attractive, but we hadn’t even had corny “cyber sex” let alone anything resembling real sex—or even a kiss, for that matter. Now suddenly he was asking for a blowjob—something he knew I had never done before.

“We’re going to the movies though,” I said. “That’s a public place.”

“We could find somewhere private.”

“I don’t think I’m comfortable with that.”

“Why? You just said you’d give a blowjob to a really hot guy you’d never see again. How is that not the exact same thing?”

At that point I realized he was talking about himself. Not only did he consider himself “really hot,” but he was confident we’d never see each other again. Somehow, this was supposed to sweeten the deal for me.

If I had an iota of self-respect, I would have blocked him immediately and moved on with my life. But I didn’t, so I just changed the subject. For some reason I still really like him. I don’t know if I actually liked him, or if I just liked who I thought he was, or the idea of him. Or maybe I just really wanted to have a boyfriend. I didn’t want to examine my motivations that closely. All I knew was how painful it would be to be rejected, and how sad I’d be to have wasted all this time—how the fun Zach I originally met a month ago had been such great company. I forgave him for the bizarre question, and a few days later when he brought up where we would meet up for our second date, I was back to being excited about him.

“Only one thing,” he said. “I’m bringing a friend, so you should too. Someone for my friend.”

“I thought it was just going to be us.”

“Yeah well my friend Randy is going to be there. He needs a date too. He likes girls with big boobs. Do you know anyone with big boobs?”

I did know a girl with big boobs—Rachel. Conveniently, Rachel was also the only girlfriend I had.

“I can bring my best friend,” I said. “If she’s available, anyway.”

By then, Rachel had broken up with her boyfriend. When I told her she was invited on our double date, I was clear with her about the facts: this guy was kind of perverted, and his friend might be a skeez too. Also, his friend specifically specified that he liked big boobs. She laughed. “Why not?” she shrugged. “I’ll go. Maybe the big boob guy will be hot.”

Rachel and I got ready for our double date at my parents’ house before going to the movie theater. This time, I wore a pink tank top and a knee-length cherry patterned skirt with a ruffle hem. Rachel wore jeans and a T-shirt. I realized there was a decent chance that Randy had envisioned Pamela Anderson, and would be disappointed when he met Rachel, who did have big boobs but also had frizzy hair, braces, and had never once touched makeup except to create artificial stubble when she was cast as a man in the ensemble of our school’s production of Hello, Dolly.

We arrived at the movie theater. Zach and Randy saw us and said hi. There was no hug, no pleasantries. We just went into the theater to watch the movie. Zach and Randy sat next to each other, barely acknowledging either one of us.

“I have to head back,” Zach said as soon as the movie was over. “Bye.”

Rachel and I sat on the front steps of the theater for the next hour after they left. I was surprised at how well she had handled the whole thing—granted, I told her not to get her hopes up, but this was more brutal than I had expected.

“Can you believe I asked my mom to pick us up an hour late in case we wanted to make out with them?” I asked incredulously.

Rachel laughed. “At least we get to hang out!”

“Yeah,” I said. “I’m sorry I made you come with me. I know it was a huge waste of time.”

“It’s okay. It was a good movie anyway. Did you actually like that guy?”

“Yeah, I guess I did. I don’t know, I don’t really like him anymore.”

“I don’t understand how you ever liked him.”

“He was different online. He was really funny and outgoing. I don’t know why he even asked me on a second date.”

When my mom picked us up, she drove us back to my house for a sleepover. I was excited to get into our pajamas and watch a girly romcom while Samantha and Felicity, the American Girl Dolls, watched us from the darkest crevices of my bedroom.

While Rachel was getting ready for bed, I opened my laptop and saw a message from Zach, but it said, “Hey, this is Randy. It isn’t Zach.”

“Hey. What’s up?”

“I just wanna tell you Zach isn’t interested. He told me to tell you. He was afraid you’d be upset and didn’t want to tell you himself.”

“Yeah, I figured that out.”

“He thought you were nice and funny and stuff but he says he doesn’t find you physically attractive. And I don’t find Rachel physically attractive either.”

“Okay I guess.”

“Sorry we wasted your time.”

I closed my laptop. Rachel had just come out of the bathroom and was ready to hang out. I would never see Zach again, so he was somewhat correct in his assumptions for the cruise scenario. I had felt so wanted during our AIM chats, not only as an object of desire but as a friend. Ultimately that was what I enjoyed about him—the fact that we could talk to each other, the fact that every day after school I had an IM waiting for me. And that night, with Rachel by my side, I realized I could just talk to her.

“Hey I have a question,” I asked her.

“Yeah?” she said.

“Okay so before I ask, I have to tell you it’s entirely hypothetical and I won’t judge you for your answer.”

“Okay.”

“It’s about a horse.”

---

In case anyone is curious: although I never saw Zach again, I did go to college with a guy who had been friends with him in high school, around the exact time all of this happened. He confirmed that he knew about the horse question, because he had been in the room—along with Zach’s other friends—when he typed it to me.