A Brief Walk Through the Shallow End

I’ve decided to tell you a story that I’ve never told anyone completely. In the times I’ve told this story before, I’ve exaggerated certain facts and completely neglected others to bend and mold the story to make myself seem better in some way. But I’ve grown kind of tired of spreading lies about myself to control perceptions. So I’m trying something new with you, dear reader: I’m telling you the truth. I’ll never be able to tell you the whole, complete truth because, well, I only have my perception of the events. But I’ll tell you those, clear as crystal, without any exaggeration or neglect. I’m just going to change some names if it’s all right. Mine is Jonathan. That’s my real name. Most folks call me Jon, but my mom still calls me Jonathan.

For high school, I went to an all-boys Catholic school in Westchester County, New York. At the time of this story, I had zero romantic experience. ZEE-ROW. Not even a kiss. I became extremely worried that I was falling behind, and that my classmates were hooking up with girls and getting laid. I wanted to get laid. That was my goal in life. And the pressure I put on myself was staggering.

I tried so hard to emulate movie characters and to cultivate what I thought was cool at every mixer, dance, and social opportunity. I lied about my own experience and acted like I’d been there before. But trying too hard and missing the mark became the norm for me, and girls all quickly looked the other way.

So when I was fifteen and a girl, who we’ll call Sheila, showed some interest in me during a get together at the end of the summer, I thought all of my cards had been played right. I figured she thought I was as cool as I pretended to be, and I was right about that. She thought I was amazing. Sheila and I had a number of mutual friends, so we had hung out on multiple occasions.

The party that night was small – less than ten people including us, and was at a very wealthy girl’s home in Northern Westchester. Growing up, my family had a four-foot-deep, above-ground pool; the round kind with aluminum siding. The house we were at this night had a huge in-ground pool, so I was all over it. I still like diving to the bottom, pressing my feet on the floor, and launching to the surface kind of like Neo in The Matrix Reloaded (which is worth revisiting, by the way).

So that’s what I was doing – Neo-launching from the deep end. I was like a fish – I must have been in and out of the pool for three hours or so. There was also a hot tub, but pffft – I was all about the pool right then. The entire group had migrated from the pool, up to the hot tub, then into the house. One of the couples in the group was separating during the school year and there was a bunch of drama. I knew the couple on a friendly basis, but not enough (I felt) to console either one. So I stuck to the pool.

Everyone was inside except for Sheila, who was dried off and sitting on the pool deck, and me, The One, rushing to the surface from the depths of the Matrix, all of nine feet down. Catching my breath, I moved over to the shallow end and we started to talk. I can’t remember how the conversation started, but I can remember my thinking the whole time:

We’re alone. They all went inside and she stayed. She wants it. She definitely wants it. Holy crap she wants it.

I should clarify that my thought “She’s flirting with me because she may actually like me,” was devolved into “She wants it,” mostly do to my seeing Animal House at a very young age. It was a piggish way to think of things, but I couldn’t help it at the time – I was stunned. And knowing that she was flirting with me, I began to think. I over think everything, and this was no exception. I’m ashamed of my thinking, but I can present it to you with the caveat that it was from the mind of younger, simpler, me. An immature teenager.

I began to pick her apart, feature by feature as she spoke. She had long, reddish-blonde hair, blue eyes, and thin eyebrows. Average height, with large breasts and hips, and her teeth were slightly crooked and a bit yellow. I was five feet seven inches, one hundred and sixty pounds, with medium brown hair, bad skin, white marks on my teeth from braces, and a tire around my stomach that still hasn’t gone away.

I began thinking that she was the least attractive of the group. In fact, she was a nice girl who was on par with me physically – In my league, and I in hers. But still it bothered me that, if things got physical with her, my first kiss was going to be with an average (or below average, in my mind at the time) girl. Pornography and celebrity gossip columns had set the bar impossibly high for me, but at the time I never considered that porn stars and celebrities were basically made to be fantastic and ultimately unattainable.

Sure, I found Sheila attractive, but I cared so much about what everyone else would think. There wasn’t a doubt in my mind that she would tell the group about us kissing or making out or whatever else I hoped was going to happen. But still she sat on the pool deck, and I stood in the pool, ever-conscious of my stomach, making sure to keep my core muscles tight and sucked in so that I looked alright to her. I kept eye contact as I moved through the shallow end to the steps, arching my shoulders back, doing my best to look like the shadow of an in-shape male.

I stepped up onto the pool deck, grabbed my towel, and stood in front of her to dry off. When you’ve got a bit of paunch, it’s impossible to bend over to dry off your legs without your stomach hanging over your waistband, so I dried off my top half and hung the towel over my shoulders. At this point, I remember we were talking about college, which was still far off. I wanted to go to film school – specifically NYU, and she was talking about Quinnipiac. I think she was interested in sports medicine. I’d never heard much about Quinnipiac, but I told her that I had only heard great things about the sports medicine program there. She concurred.

There was a lull in the conversation and my heart started picking up a bit. I was looking at her, sitting down, towel wrapped around her bottom half, leaning toward me. As soon as I glanced at her chest, my mind started racing as fast as my pulse. I looked away so as not to stare, and then I saw it: Behind her, off to the side of the yard, there was a wooden jungle gym – Monkey bars, two swings, and little hut with a slide. I knew what I was going to do next, though I was sure it wouldn’t work.

I asked, “Have you ever seen Spider-Man?”

She looked at me, confused. “Yeah.”



“Nothing, just thinking about it. Good movie.”


“Toby Maguire is a terrible choice for Peter Parker, but yeah. Good movie.” I knew where I wanted to go with this and I started walking over to the jungle gym, rambling about Sam Raimi’s influence on the Spider-Man series (specifically: his deciding that web-shooters were not a gadget of Peter’s, but a biological mutation). I was unsure of how to keep this conversation thread going, but to my surprise, she followed.

My bathing suit, sopping wet, made squishing noises with every step I took. My heart was really revving now, but I pressed on. I threw my towel on to one of the swings and began to climb the monkey bars. I swung across, trying to look as muscular as possible on the way, until I reached a small window on the wall of the wooden hut and hung there.

“What are you doing?” I had forgotten for a minute that she was right behind me. When I swung across, I had taken my sweet time because a.) I was out of breath and b.) When you’re hanging from the monkey bars, the paunch is invisible – I looked great. I think.

“I’m gonna try something,” I said, still trying to keep my cool.

“I can see that, but what?”

I stuck my legs through the hut window and held on to the window frame. She was closer now, and I looked over my shoulder to make sure I wouldn’t hit her as I reclined to let myself hang down, Spidey-Style. I thought it was going to be the coolest thing EVER. I would recline all smooth-like, and hanging there, I’d say “Okay, now kiss me.”

I didn’t take into account how much pain I’d be in, with the wood digging into the backs of my legs, nor the strength that the whole maneuver requires in general. So when I snapped backward into position, reclining too fast, slapping my hands against the play hut to stop myself from hitting my head, I sounded a little more flummoxed than I anticipated:


She rushed in and started kissing me, holding my head and stroking my chlorinated hair as I gripped the wall for dear life. Kissing upside down is not nearly as interesting as it looks in Spider-Man. Our top teeth kept grinding together and we kept missing each other. And because we kept missing each other, she grabbed my head a little harder to keep us steady.

So there I was: Hanging upside down, blood rushing to my head, legs throbbing in pain, teeth grinding, water from my bathing suit dripping into my nose… my first kiss.

I leaned away from her and pulled myself up. I climbed down, legs like spaghetti, and approached her.

“Okay,” I said, “Let’s try that again.”

Kissing her right side up was a little better, and much easier. We kissed a little longer and then walked back to the pool deck. We sat together on the lounge chair and talked a little more before going back inside. I said nothing of what we had done, nor did she. But for the rest of the night we’d exchange glances and she’d smile.

I awoke the next morning after everyone else had already started eating breakfast. When I came into the kitchen, everyone stopped talking. They were cleaning up and getting ready to leave. I followed suit.

I didn’t speak to Sheila very much after that, if at all. We exchanged hellos here and there, but never more than that. I haven’t spoken to her since high school. One night during my freshman year in college I decided to look at her Facebook, but she had de-friended me. I suspect I looked like quite an idiot in flirting, making out, and basically leaving her alone. I have no ill will toward her. I was indeed an idiot.

I often wonder if she knows that she was my first kiss. I wonder if I was hers. I also wonder what that time of my life would have been like if I hadn’t been so fixated on how I would be perceived by my friends. But I’ll never truly know, and I think that that’s the price that I’ve paid for being so shallow.

(photo courtesy of think4photop/FreeDigitalPhotos.net)

About Jonathan Robertson

Jonathan Robertson has been telling stories ever since he broke his mother’s crystal candelabra with a big ball of masking tape (“I swear, the dog did it.”). Since then, he’s written a number of short stories and essays, and directed several films. Currently, he produces a television show and uses that as an excuse to travel as much as possible and to pursue his dream of devoting an entire half hour of television to the process of making beef jerky. (Stay tuned.) Feel free to check out his latest films at vimeo.com/jonathanrobertson.

About Jonathan Robertson

Jonathan Robertson has been telling stories ever since he broke his mother’s crystal candelabra with a big ball of masking tape (“I swear, the dog did it.”). Since then, he’s written a number of short stories and essays, and directed several films. Currently, he produces a television show and uses that as an excuse to travel as much as possible and to pursue his dream of devoting an entire half hour of television to the process of making beef jerky. (Stay tuned.) Feel free to check out his latest films at vimeo.com/jonathanrobertson.