The Pilot by Catherine Johnson



The Pilot

noun: 1. a person who operates the flying controls of an aircraft

2. a television program made to test audience reaction with a view to the production of a series

adjective: done as an experiment or test before introducing something more widely



It wasn’t until I had sex with the pilot that I learned how to ask for what I wanted in bed. I realized that what I really wanted couldn’t be asked for, or found there, especially if I kept lying to myself.


I met the pilot at the beginning of 2019 in Portland, Oregon. I moved there three years earlier for graduate school, and since completing an MFA in creative writing, had been doing the adjunct hustle—teaching and tutoring on four different campuses around the city. I grabbed odd jobs to keep up with my bills, all the while trying to write. I spent a year being intentionally single and self-focused after the end of a serious relationship in 2018, and was finally ready to date. So like many urban-dwelling thirty-somethings, I went online.


When I created my Bumble profile that January, I told myself I probably wouldn’t meet someone I really liked, but online dating was good practice. When getting a date for Friday night could be as easy (not always easy, but sometimes) as swiping for twenty minutes, the stakes felt lower. I could show up and be myself and not try too hard to hold someone’s interest. It was with this attitude that I ambitiously scheduled three dates with three different men in the second week of that January.


The first man began our date by boasting about his brand-new red sports car. “I had a hard time finding parking,” he said before removing his pea coat and maroon scarf and launching into the details of his recent purchase. I nodded politely. After we’d ordered our cocktails and settled into a quiet, candle-lit corner, he took control of the conversation with a series of questions: “What are you looking for? What habits or patterns do you have in relationships?” He wasn’t wasting any time with chit-chat about the weather. This was a man on a mission.

I knew pretty quickly that we were not a match, but this was a fun game and I appreciated his forthrightness. He unapologetically came out and said he was looking for his future wife and the mother of his children. When dating in your thirties, there’s a biological urgency that compels people to get real.

“I don’t think I want children,” I said. “I don’t need to get married” and “I have a tendency to keep things to myself, to not say how I’m feeling or ask for what I want.”

Looking at my last relationships, I noticed a pattern I wanted to break. Both of my previous partners were sweet and caring. There were no problems, no fighting, and at the time I thought this was a good thing. But eventually I wondered if it meant I just wasn’t that invested. Was I in love? Was that what it’s supposed to feel like? On some level, I knew the answer was no, but I put those thoughts aside. It was so easy to be with them, so it must have been right, I reasoned. But the unease grew until it couldn’t be denied or contained, until I knew we had to break up, which I instigated—to the shock and confusion of both men. I had given little indication that I was unhappy, and so they felt blindsided.

I hadn’t intended to be deceptive. I didn’t like that I denied my feelings until I couldn’t stand them, ripping away our connection like a band-aid in a single confession. I was determined never to do that again. Next time, I would be honest and communicate. Next time, I would acknowledge and say what I wanted and needed. I told this to the man with the sports car and we had a pleasant, truthful two-hour conversation. I never spoke to him again.


The second guy I went out with worked for Harley Davidson. He was an inch taller than me, which meant he felt shorter than me, and drove a truck so large that it automatically dispensed a step from which to hoist oneself into the cab. Inspired and emboldened by my first date, I began this date by saying, “So, give me the Cliff Notes version of your life story.” I just wanted a bare-bones sketch of where he’d been and what he’d been up to so I could get a general sense of who he was.

“What is this, an interview?” he retorted.

“I wasn’t trying to interrogate you.”

He reluctantly answered the question, and the next hour of the date stumbled along awkwardly with me asking most of the questions. We turned to talking about politics and economics, and things got more interesting. I accepted his offer for a second round of drinks, and a third. Again, I had that gut feeling that this wouldn’t go very far, but I was enjoying myself nonetheless.

At the end of the date, as I catapulted myself into the passenger seat of his truck for a ride home, I noticed a car seat in the back. His minilife story had failed to include his three-year-old son.


Of the three dates I scheduled that week, I was most eager to meet the pilot. His profile said he was a search-and-rescue helicopter pilot (sexy) and a writer (me too), and he listed his parents as one of his interests (sweet). He was eight years older than me, and during our initial messages he addressed me as “Miss C.” I suggested we meet in my neighborhood, at a 1960s living room-inspired cocktail lounge with a freestanding gas stove fireplace, DJs observing a diet of Motown and funk on the turntable, and lingering French fry aromatics. When I walked in, he was sitting at the end of the bar with a shot of whiskey and a pint of beer to his right, a Chuck Klosterman paperback rolled up in his hands, and illuminated by a votive candle in a glowing red hobnail holder.

The bar was busy that night, and he stood to greet me. I removed my winter layers, climbed onto the stool next to him, and ordered whatever whiskey he was drinking, neat. Instead of diving in with my repertoire of getting-to-know-you questions, I asked how he was liking Klosterman, one of my favorite writers. Our conversation carried on in this vein, riffing on one another’s knowledge of books, and then movies.

I was immediately attracted to his dry humor, the subtle twang in his voice, the way he glanced at me out of the corner of his eye and spoke in semi-abstractions that left me curious, reaching to put together what he meant. There was a weathered, old-Portland curmudgeonliness to him that I found endearing. In a wistful, that’s-the-way-it-goes kind of way, he lamented the way the city he’d grown up in was changing. He appreciated aesthetics, and commented on the workmanship of the bar inlaid with old keys (the cocktail lounge was in an old locksmith building, built in 1962) and the quality of the lighting. I liked that he paid attention to details and his style—simple but deliberate: hoodie, denim, baseball cap.

We talked for over three hours before he hailed a rideshare and I started walking home. As we parted, he said, “You’re all right,” as if I was more than all right. “If you want to hang out again, text me,” he said. I told him I already knew I wanted to hang out again. But he insisted I wait. “Not tonight. Text me in the morning,” he said, as if he didn’t trust that I liked him after three pours of Buffalo Trace.

At 8:59 a.m. the following morning, I texted him, “Good morning! When are we hanging out again?”


In Chuck Klosterman’s essay “This Is Emo,” he blames John Cusack for his failed love life in the late 1980s. He writes that the romantic ideal of Cusack’s character Lloyd Dobler in Say Anything was so culturally powerful that he couldn’t compete. That’s what women wanted, and they would sacrifice real-life romance in order to chase this holy grail of love. Movies and TV have warped our romantic expectations. They peddle “fake love” so that we are continually disappointed by our real-life partners. Fake love, Klosterman says, is manifested throughout popular culture: the unbearable sappiness of Coldplay, Bridget Jones’s happy ending. “The main problem with mass media is that it makes it impossible to fall in love with any acumen of normalcy. There is no ‘normal’ because everybody is being twisted by the same sources simultaneously.”

I loved that essay when I first read it over a decade ago. It confirmed my growing disillusionment and the idea that any one person could satisfy all of one’s needs. My weariness of soul mates and the you-complete-me sentiment touted in romantic comedies led me to not only bristle at these clichés but think maybe I didn’t really need a partner at all. By the time I started dating that January, I was feeling especially evolved. I wrote on my profile that I was looking for an honest connection. I didn’t want frivolous sex (I’d checked that box in my twenties), but I didn’t think I needed a traditionally committed relationship either. After all, kids and marriage were not my priorities and I loved the freedom of being single. My life was full and complete; romantic intimacy was just a bonus. I wanted companionship. Intelligent conversation. Good sex. Real honesty. I was not looking for my Lloyd Dobler.


On our second date, the pilot and I met for a drink and saw a boring black-and-white art house foreign film. We took a short walk around the neighborhood and went our separate ways. I didn’t know if I’d hear from him, or if I would make the effort to contact him. Our energy felt muted on the second date. But a few days later, he reached out, texting: “If you could be up for traversing the city and curling up on the couch with me for a movie and some chewing of the fat, let me know. Would attempt to give you a high class back massage. (I’m a scoundrel, I realize.)”

Up until that point, I didn’t know if he was physically attracted to me. I thought he was very cute, but I couldn’t read his body language. Was he flirting? Was he into my flirting? So I was surprised by the proposition of cuddling—made all the more palatable by a Han Solo reference. I accepted his invitation.

He lived in an old craftsman that he was restoring. Every piece of furniture in his house was carefully chosen: an antique pheasant loveseat, a standing Tiffany lamp, and a freshly refinished coffee table that, he said, “looks good enough to be respectable, but not so good that you wouldn’t put your feet on it.” We sat on his sofa, ate, drank, and watched Raiders of the Lost Ark—selected precisely because we’d both seen it so many times. We could chat, recite our favorite lines of dialogue, and marvel at well-executed shots.

Eventually, he took one of my hands in his and commenced his promised massage by pinching the flesh between my thumb and forefinger, kneading my palm and fingers. Before Indy and Marion rekindled their past and escaped the Nazis, he and I were spooning on his couch. His arms were locked around my body, squeezing my body tightly, almost too tightly. I relaxed into him, and could smell his musky skin. He pressed his lips firmly against my cheek; I turned and kissed him.


When I was in my 20s, guys complained that I never asked for what I wanted. What did I want to drink tonight? Where did I want to eat? I didn’t care, I’d say. I thought I was easy going, low-maintenance. But honestly, I could no more say what I wanted for dinner than I could name what I wanted in bed. Just tell me where to put my legs, and let’s do it.

I always dreaded: “What’s your favorite position?” It revealed the limits of my sexual self-awareness. Eventually I started saying, “I like being on top.” This became true, but at first it had little to do with maximizing my pleasure and more to do with looking experienced; it was the answer of a woman who wanted to consider herself a feminist.

 In retrospect, I did know what I wanted; I just didn’t know how to ask for it, or if I should want it to begin with. I didn’t want to be the girl who liked hand-holding, check-in phone calls at bedtime, or spontaneous gestures of affection. So I remained silent—I couldn’t be judged for my desires if no one knew what they were.

I learned to voice opinions and ask for things, but my questions and answers were carefully constructed and tightly controlled—nothing uncomfortable or vulnerable. I muted my feeling as if something precious would break if I revealed myself, but I fantasized about being cracked wide open.

Before I began dating that January, I was worried about my lack of sexual desire. For several years I’d been dealing with low estrogen issues and thought it might be connected to my low libido and the fact that I almost never thought about sex. After the third date with the pilot, I stopped worrying. Things were fully operational, and I was sprung. I knew it was largely a chemical response—oxytocin and endorphins flooding my brain. Of course, I liked him, but so much of my reaction felt purely corporeal. I couldn’t stop thinking about the touching, holding, kissing. It consumed my mental space. I worried people would see my thoughts, that my wanting was smeared all over my face.

After a month, I started sleeping with the pilot. I felt like I knew what I wanted in bed, though I still hesitated to ask. I used to need alcohol in order to have sex, to slip into the role I thought my partner wanted. In my thirties, I used alcohol to release more of myself, to take risks. I followed my body’s hunger and pursued pleasure, though I still had a hard time asking. The pilot created a space where I could ask for what I wanted—not by asking me rote questions about my favorite position or my sexual fantasies (another question I used to hate) but by telling me what he wanted.

His first request came over text message after texting plans for our next date: “Also, I’m a closeted sex machine who’s trying to be slow and classy, but who is really excitable and wants to do all sorts of enjoyable things with you! Just putting that out there.” He proceeded to list those enjoyable things: “touching and kissing and gripping and rubbing and stroking and tonguing and watching and pleasuring and being pleasured.” I didn’t know how to respond. Was I creeped out by this? I was not. I was flushed with excitement and amazed by his ability to come out and ask for what he wanted—name his desire. It’s not that no one had ever said stuff like this to me before. But it wasn’t until then that I noticed it in this way—someone asking for what he wanted. Why don’t I do that?

The next time the pilot combed his fingers through my short hair, fist closing and tugging gently, I asked for what I wanted: “Pull harder.”


There was still an underlying insecurity that bubbled up from time to time, but with the pilot I rarely felt like I could be too much. I didn’t need to ask to take up space; I could just take it. And I liked the way he took up space. Sometimes he’d comment on his love handles, the little extra padding above his hips, and how hard they were to lose as he got older. I liked them. They put me at ease with the way my own body spilled over in places.

He paid attention to the way he dressed, to the words he used, to how I felt during sex. He’d comment on the specific way my leg bent, or the muscles in my back. He complimented parts of my body that I usually tried to hide. And his own satisfaction was clearly connected to mine. I almost never had to ask for reciprocation—it was more common to ask him to stop making me come. The one time I did ask for reciprocation, he finished first and I was still squirming in my own heat. I asked him to touch me, and he said, “Of course. Never hesitate to ask for that.”

I felt free to explore the boundaries of my physical desire, to test the threshold of pleasure and pain where two collide and become indistinguishable. I trusted him when he pulled my hair, or dug his fingers into my hips, or placed his palm at the base of my neck—inducing chills and goosebumps that stole my breath.

I felt seen.


I was still learning to ask for what I wanted sexually, and felt more comfortable and honest in my skin, but I was distressed by an undercurrent of dissatisfaction. Despite our engaging conversations over the last three months about books and politics, despite the great sex, I didn’t feel like I really knew the pilot,or that he was getting to know me. Perhaps because I liked him, it was hard to muster the courage to ask intimate questions. My experiment in honesty had hit a wall. Our connection wasn’t dishonest; it just felt—restrained.

The pilot liked to write but did not consider himself a real writer. He constantly downplayed his legitimacy. He’d spend a whole morning revising a single paragraph. When we were still exchanging messages through Bumble, we connected over our mutual love of jump-starting creativity with jitter-inducing quantities of caffeine. Once we started hanging out, we’d text one another pictures of us presumably getting to work: his manuscript and Americano in a cafe, my laptop and coffee mug on my desk. He’d text things like “Let’s geek out and write together!” He chose his words carefully, deliberately. He’d apologize for, and correct, accidental misuses of punctuation. Our texting was a ping-pong match of nerdy wordplay, including diatribes about the abuse of exclamation marks and defenses of the Oxford comma, but for all the words that bandied between us, few of them did what words do best: explore, examine, expose.

In addition, we shared almost no sleeping hours together. On our third date, we established that neither of us is fond of sharing a bed. I am not a sleep-cuddler. I like to cuddle right until I want to sleep and then I do not want to be touched until morning. I also resent being confined to half a mattress—usually balled up in a fetal position, worried about breaching my designated side. I need to roll and sprawl, tummy-up and legs splayed, or belly-down and cupping the four corners with hands and toes. I need freedom to move.

“If I ever live with a partner,” I warned him, “I’ll require a king-size bed.”

“I’ve always liked the idea of having separate bedrooms,” he said, an option I’ve also found appealing, if not more so, because it suggests retaining one’s autonomy, like keeping your last name. “I like to be a starfish,” he added.

Each time we hung out, we rested for a while in one another’s arms before excusing ourselves to our respective homes. And while I appreciated this space and preserving the quality of my sleep (which feels more and more precarious the older I get), there is an intimacy that grows from sharing unconscious hours. I didn’t think I needed a relationship per se. I just wanted to know him better, the way I know my good friends. The moments before you fall asleep with someone and the moments after you wake up are uniquely suited to this kind of intimacy.

There was also the fact that not sleeping over meant not sleeping together in the morning. It was not unusual to receive an a.m. text message from him pining for such a thing, and I often prefer sex in the morning. Then one evening at my place, after sex, after a ten o’clock dinner of chicken fajitas, I proposed we give sleeping together a try (for the morning sex, of course) despite our starfish proclivities. He agreed immediately, with the understanding that if sharing a bed wasn’t working, the host would retire to the couch. A contingency plan.

On the night that I slept over at the pilot’s house, we sat in his bed reading our respective books. I glanced at him from the corner of my eye, trying to gauge how immersed he was in the Patricia Highsmith biography he’d just bought.

“I don’t want to read,” I finally declared after minutes of deliberation, thrusting my bookmark into place and putting the book aside. “I want to talk.”


“No,” I said, “not like that. I just want to talk. I just want to know you better.”

“OK, what do you want to talk about?” he said.

“What happened in your last relationship? Why didn’t it work out?”

He thought about this for a moment and then began to talk. He talked for a while, even answering other questions I hadn’t yet asked, gradually filling in more and more of his mystery. I turned on my side to show I was listening. He rarely looked at me as he spoke. He gazed straight ahead or into his book, which was still open and teetering on his lap as if he would return to it at any moment. He shared things I could tell were not easy for him to say, things about his past, things about the present.

What came next was not an exchange—he finished, he was finished. He was supposed to ask me the same questions in return. He asked nothing. He didn’t have the bandwidth to share anything more than his own story.

I didn’t know what to do or say next. I think I just thanked him for sharing, perhaps touched his arm or back as a gesture of acknowledgement. And then I let him return to the words in front of him. I had no interest in reading, so I rolled over onto my side of the bed, knees bent, small, and attempted sleep.


When I was in graduate school, I took a literature class on Charles Dickens’s Great Expectations. I remember my professor explaining that Pip’s story was really a story about misreading one’s life. When orphaned Pip receives a fortune from a mysterious benefactor, he assumes it’s from the wealthy Miss Havisham. And after months of visiting Miss Havisham’s beautiful but contemptuous ward Estella, under the hopes that Miss Havisham was grooming him to be a gentleman so he could marry Estella, Pip discovers the situation is not at all what he’d thought. Miss Havisham was not his benefactor but a criminal named Magwitch whom Pip encountered earlier and who was moved to reciprocate Pip’s kindness. Miss Havisham never had any intention of marrying him to Estella but rather of training her to be cruel to men (in revenge for her own nuptial abandonment) and using Pip as practice.

Since that class, I’ve often thought about how I read or misread my own life. The process of getting to know someone is nothing if not an exercise in reading—putting together disparate events, organizing their chronology, coloring in the gaps—until a cohesive narrative emerges. Part of a complete story is an honest emotional thread that goes beyond the who, what, where, when to the why of a person.

I never grasped the pilot’s why. What he told me that night in bed helped. I was glad I’d asked, and it felt better to have more of his context. But the door I was hoping to burst open was stuck ajar and I still felt locked out. He gave me the answers I’d asked for, but without an exchange, without him asking those same questions in turn, it wasn’t enough. That is what I really wanted—to know each other. To reveal my own why. I wanted him to see me with the kind of attention he focused on my body (and his house, and his words). The honest connection I craved was really a craving to be seen, to be known. The real problem wasn’t that I couldn’t ask for what I wanted (I was learning) but that I wouldn’t let myself say what I wanted. I still worried my desire to be known was akin to asking to fall in love, and I didn’t think I “should” need that. I wanted to be beyond that. But what is the difference between being known and falling in love? Only words.

In my mind, falling in love was banal, synonymous with Klosterman’s fake love. I was scared to admit that maybe there was something to be said of falling in love and that my desires might be the same as most people’s.

When I realized that my relationship with the pilot would never be what I really wanted, I wasn’t sure what to do. I enjoyed my time with him, and we weren’t committed to each other. So why not just keep having fun while keeping my eyes open? And yet if I knew what I wanted, why waste my time not pursuing it? Fortunately, life circumstances intervened. Tired of the adjunct rat race and the rising cost of living in Portland, I applied for full-time teaching jobs across the Mountain West and was lucky to land one in Laramie, Wyoming, a small college town just north of the Colorado border.

I savored my last Portland summer and remaining time with the pilot, who congratulated me on my new employment and the affordable life and big skies that awaited me. On our last date, we had cocktails and sex and saw a movie at the Hollywood Theater. As we unlocked our bicycles and prepared to go our separate ways, likely for the last time, I wondered if there would, finally, be any talk of feelings, any it was good spending the last seven months hanging out, no major declarations, just a nice knowing you. But there wasn’t. We said goodbye like we always did. I guess he didn’t have the bandwidth for that either.


As I rode across town, down Broadway, then zig-zagged through NE Portland’s foliaged neighborhoods and unattainable craftsmen homes, feeling a little of everything—sad, wistful, relieved—I wondered how much I was actually willing to let myself be seen. If he had returned my questions that night in bed, what would I have said? Would I have been honest? Open? Or would I have carefully chosen my words and crafted my answers, like I usually did, to once again project the image of myself that I’ve deemed lovable?

My experiment in online dating not only revealed the depths of my own dishonesty but that I needed to be a better teller of my own story because there is no honest connection without first owning my desires. And I do desire—to be cracked wide open.


Catherine Johnson’s work has been published in Oregon Humanities, Propeller, Gulf Stream Magazine, STORGY, Portland Monthly, the Los Angeles Review, Nowhere travel magazine, and is forthcoming in Hypertext, Kithe, and the anthology Evergreen: Fairy Tales, Essays & Fables from the Dark Northwest. She has an MFA in creative nonfiction from Portland State University, and is now an assistant lecturer at the University of Wyoming, in Laramie.

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