My phone vibrated in my pocket. It was the pilot. “Hey, what’s up?” I said, staring at a wall of cutesy stickers. I was at a stationary store, shopping for decorations for the trendy Japanese planner I’d bought to start off the year.
“Are you free for a minute?” The pilot asked. I looked around at the busy but quiet store, self-conscious of being that person. Still, my curiosity overrode my self-consciousness. It was too cold to step outside and take his call. We would make this brief.
“Yeah, I can talk,” I said.
“Okay, that’s great. I just wanted to let you know that I’ve been on a handful of dates with someone else, and we’ve decided we’re going to pursue a relationship.”
“Oh! Okay,” I said, my heart sinking just a little. I knew we didn’t connect romantically, or, sexually. Strongly suspected he was gay, in fact, which eased the blow of the rejection. Even still, a rejection was a rejection. I badly wanted to ask whether this person, this “someone else,” was a man or a woman – making note of the fact that he hadn’t specified the gender. I held myself back though. Didn’t want to tread on a sensitive subject, him being closeted and all.
As soon as we hung up, I realized that I should’ve asked about us remaining friends. It would’ve been much more natural as part of our conversation, rather than a text afterwards. He’d kind of put me on the spot though, and I dropped the ball. Instead of asking on our call, I sent him a quick text. “Btw, I should’ve said this on the phone. I know we didn’t necessarily have a sexual spark but I enjoy your company if you want to be friends! Otherwise, if you feel like that would distract from your relationship, I totally get that.” Minutes passed with no response, then hours, then days. Ghosted.
I looked him up on Instagram. The only thing publicly linked to him was a photo of his smiling face in the cockpit of a 737, posted by the National Gay Pilots Association from 2020. “We love our allies! Thank you to all our members, including ally [REDACTED], for all that you do in the name of inclusion and equality [insert pride flag, insert heart emoji].” I flipped back to his Hinge profile, making double sure he’d marked his sexual orientation as “Straight”, thinking maybe I’d overlooked that important detail. He had though. It broke my heart then, seeing him staring out at me from my screen – from Instagram and Hinge – pretending to be someone he so clearly wasn’t.
To back up just a little bit, I’d met the pilot twice. Once on Tuesday of that week, and once on Thursday. We met up for drinks on Tuesday at a swanky new cocktail bar around the corner from my apartment. From cocktail bar number one, we migrated over to cocktail bar number two – another similar place that we’d previously joked was a Chicago first date classic. He was a little strange, in an endearing way. He spoke in clipped sentences and smiled wryly. It took me a little while to clock that he was indeed enjoying our conversation. He told me all about his parents’ split. How his dad was a rich asshole, a serial cheater from Highland Park who went in on a midlife crisis yacht purchase with his divorce attorney. When the pilot was only eight years old, his dad would bring him out on the boat with him and a bunch of “girls” with “gross big boobs” (his words, not mine – which began to tip me off) to party. The pilot, as a kid, would bury his nose in children’s books at the far end of the boat, away from the girls and his philandering father. The pilots’ parents clearly had money. He told me they had been founding members at the prestigious Chicago gym, East Bank Club; told me he drove there most days to take spin classes when he wasn’t working a flight. I pictured him then at the front of the class, the only guy amongst a sea of hot women.
His older brother, meanwhile, was an accomplished minimally-invasive neurosurgeon in Connecticut, with whom the pilot spoke every day. “He always picks up my calls, even when he’s in the OR,” he explained. They were extremely close. When his brother was in residency in Missouri, he’d hired the pilot, who was between jobs at the time, to move in with him and his OBGYN resident wife to take care of their baby. Again, this endeared me to the pilot, and tipped me off even further – thinking of him as a live-in nanny to his brother’s child. Since his days in Minnesota, his brother and his family had moved to the east coast, the pilot’s mother trailing close behind. The pilot, in that time, had gone back to Chicago where he was originally from, and had launched what appeared to be an immensely successful career with American Airlines.
I’d been really excited to meet a pilot in real life. I had so many questions for him, and warned him ahead of time that I might need to interview him. Is the Mile High club even physically possible? Did you watch Nathan Fielder’s The Rehearsal? Was it accurate in its portrayal of commercial pilots? What is the dynamic like with your co-pilot? With the flight attendants? Are you really active the whole flight, or are you just kind of hitting some buttons at the beginning and end of our journey through the air? I learned quite a bit from him. That the Mile High club is likely an impossibility for passengers, but highly plausible for flight attendants working certain long-haul international flights, where they actually have their own bunk onboard for sleeping. Apparently it happens all the time. And yes, The Rehearsal was somewhat accurate. If you check your schedule and you’re flying with a co-pilot you know, you’d likely text ahead of time because it’s an exciting “coincidence”. Otherwise, you might totally ignore the other guy until you’re in the cockpit.
The pilot claimed he was one of ten Jewish people out of 17,000 pilots working for American Airlines. Another was a really good-looking guy his age from Long Island living in Scottsdale named Blake, who typically went for older women. The pilot talked so much about him, he probably had a thing for Blake. He’d just tried to set Blake up with a 60s-something flight attendant, who – in Blake’s words – “was probably very attractive when we first hired her.” In terms of the dynamics with the flight attendants, a lot of them partied together. Would stay in the same hotels with flight attendants and pilots from other airlines and get drunk together on long layovers. KLM would party in South Beach with American. The Delta girls were sleeping with JetBlue pilots. It was a whole other world, unbeknownst to most weary travelers. “What do you normally eat when you’re flying?” I asked. “I’ll usually have one of the stewardesses bring me my hot girl dinner – a Diet Coke and two bags of pretzels,” he said. Swoon. Man after my own heart.
Soon, the conversation drifted from family and work to more salacious topics. I don’t remember exactly how we landed there, but his words are as clear as day in my memory. “I’m much more interested in parts I don’t have than those I do,” he insisted. It was an odd thing to say on a first date – an odd thing to say, period – but maybe he’d read my mind. After all, I had been wondering. I didn’t really believe him on this topic, but I laughed politely and agreed. We left the second bar and it was freezing out. With windchill, we were somewhere in the early negatives. “I’m going this way,” I said, pointing in the direction of my apartment where I needed to turn. There was no question of a hug or a kiss, as there sometimes was at the end of a first date. Instead, he just kept walking and waved goodbye. That was kind of weird. Maybe he just wasn’t interested, I told myself after we’d parted ways. The conversation had been good, I thought, but he’d left so abruptly. To make myself feel better, I reminded myself then that in all likelihood, it wasn’t personal. It seemed like he might just not be interested in women, period. He’d made one comment about my looking beautiful, but in a generic, detached sort of way – more in the way that someone can appreciate someone else’s attractiveness without being attracted to them, per se.
Despite our hurried goodbye, he texted me the next morning from his spin class at East Bank Club. “So it appeared at first it was me and the Gold Coast moms based on my parking situation but the class is 50/50 men/women but I am the youngest guy – late 40s+.” Oh! I thought to myself. So our conversation continues, after all. We’d talked about it the night prior, a little bit. Whether he was typically one of the only guys in his workout classes. He was, sometimes, but it didn’t bother him.
He’d told me, on date number one, that he was getting his apartment painted the next day. Nice, bougie paint, he said, telling me the brand name, Farrow & Ball. Chantilly lace, the color was called. It was $7 grand in total, to have his whole place done. He had a way of doing that – of dropping money into the conversation – in a way that icked me out, ever so slightly. Men in general, I’d noticed, had a tendency to do that on dates. To flex in a way they thought was subtle, but really wasn’t. He’d brought up his three bed, two bath in Logan Square multiple times. The two cars he’d had imported from Japan. Like, I got it. You don’t need to hit me over the head with this information. Anyway, in the course of our back and forth via text about the paint job and workout classes, we decided to make a plan for later that week. He was leaving the following Monday for a clothing optional vacation in Mexico with his gay friends (yes, you heard that right, clothing optional), so we needed to get something on the books in short order. He suggested a comedy show on Thursday, and I agreed.
We met at the Lincoln Lodge in Logan Square, which I’d been to a couple times before. Was curious to see how the night would go. After all, live comedy could be so hit or miss, and I was kind of nervous to get roasted in the audience on a second date. Fortunately, the pilot and I were on the same page, and we sat far from the stage, our backs against the wall. The comedians chose other people to pick on, thank god. Two bros who’d met as undergrads at Savannah College of Art and Design – a graphic designer and a construction worker fresh off a breakup. They were good sports, the bros, and the crowdwork was excellent. We laughed a lot, and from the comedy club, decided to get a drink near his place. We jumped into the Japanese Kei truck he’d imported. He needed to register it in Montana because the driver’s and passenger’s sides were reversed. “How is this legal?” I asked. It barely was, from the sound of it. “Was it weird, driving on the wrong side, at first?” I asked. “Oh I was driving in the middle of the road, for a while there,” the pilot said. He’d imported this (which had come in white and he’d had painted a bold seafoam green) and a convertible, he explained. Neither was practical. Neither was fit to be taken on the highway. But good for flexing on the way to and from Logan and East Bank Club.
Once at the bar, it felt like a flip switched. Or didn’t switch so much as it felt like the lights came fully on. Any doubt that was left that he might be gay dissapated. The more we talked, the more it became abundantly obvious. We talked at length about so-called “straight” guys being downlow gay. He’d gone to pilot school at the University of North Dakota and had been in a frat there. He recounted going downstairs to the basement to do his laundry and walking in on one of his frat brothers blowing another. “I didn’t interrupt them, really! Just asked if they didn’t mind moving my clothes to the dryer when the wash cycle was done. And they did!” He told me, laughing. From there, we moved onto the topic of glory holes. Where they were, what apps guys used to find them, the whole gamut. He told me he preferred women’s jeans because they fit better, and mentioned wanting to put on my top later that night. He even “joked” about wearing women’s panties! The ways in which they did and didn’t work with male anatomy. At one point, he said something “sucked dick” before immediately correcting himself. “I probably shouldn’t say that,” he said. “Sucking dick probably isn’t so bad.”
While we were sitting there at the bar, a text popped up from his best friend, a flight attendant (also gay). He showed me the background of their text thread. I didn’t even realize that was something you could customize on the iPhone, but sure enough, theirs was a 737 with the pride flag on it that read “GAY” in all caps. “Watch,” the pilot said. “If I change it to a plain background, he’ll switch it back immediately.” He changed it to basic white in front of me and sure enough, as soon as his friend noticed, it switched back to the pride plane. Clearly, the pilot’s identity was an open secret.
We left the bar and walked back to his place. His apartment was gorgeous. Easily the biggest and most beautiful place I’d seen since moving to Chicago. As he gave me the full tour, he inhaled. “See, the paint they used is so high quality, it even smells good.” He poured me a glass of water and we sat down on the couch, facing each other. We talked for a while, which evolved into making out. It wasn’t bad, per se, but it was strange. I was kissing a gay man. Although we were both consenting adults, I felt weird about it, knowing with near certainty that he wasn’t actually attracted to me. “What if he’s bi?” Friends asked when I later recounted the story. Maybe. Maybe bi, I conceded. But nothing about his behavior, actions, or vibe was giving interested in women. To me, he read as a straight-up gay man.
After a little while, before anything could really progress, he pulled away. “I’m sorry,” he said. “I’m a bit in my head here. Next time we should go to your place,” he suggested. I looked around at his expansive apartment, and thought about my much smaller one, in comparison. “Okay, but it’s nowhere near as nice as yours,” I said. “That’s okay,” he said. “I have too many bad memories here.” He’d alluded, the first time I’d met him, to an ex who was narcissistic and even abusive. Who would scream at him and worse. A flight attendant (also for American Airlines), who he’d matched with on a dating app. I’ll assume here that he was telling the truth, and this was indeed a female flight attendant, whom he’d dated, so I’ll refer to said ex with the pronoun she. She’d moved in with him, into the beautiful Logan apartment. Sitting there on the couch then, facing each other, he explained to me why he’d had the space repainted in Chantilly Lace. She’d been physically abusive, too. Had thrown pots and pans at the wall. Left marks. “I couldn’t walk past that spot anymore, knowing what she’d done.”
We sat there for a while more and just talked. I was so endeared for him. Felt protective of him, even. Thought of him, once I’d left, alone in this stunning apartment. Way too big for one person. “It sleeps ten,” he’d told me on our tour. The walls freshly painted, a symbolic and literal bid to cover up the trauma in his recent past. I had the urge to hold him. To love him, even. A platonic love. There was a bittersweetness when I left. Confused, a little bit. But not really. There wasn’t much left to figure out. He told me to text when I got home, which I did. Said he had a great time. Texted me the next morning a link to a new dating show he wanted his cougar-chasing friend Blake to go on. “Is it too early to razz people?” He asked.
We chatted throughout the course of the weekend. Normal “talking stage” stuff. I wondered a bit about how we could proceed. He’d broken me open, on some level. Endeared me very deeply to him. And yet, it obviously couldn’t be. Maybe I could be with a gay man, though. Maybe I could make that work, I decided. It caught me by surprise when he called that Sunday, only insofar as he didn’t really need to pick up the phone to tell me that it was over, after only two dates. More evidence that he was likely a thoughtful, considerate gay man. Most straight guys would never. What did catch me by surprise was how hard it landed with me. How quickly I’d become attached to him. To this man so obviously living a lie. He’d tugged on my heartstrings, in all his vulnerability. I wondered why this person – who so clearly surrounded himself with gay men – felt like he still couldn’t come out, at 36. I thought of his asshole dad, with his expensive boats and his serial cheating, and speculated that he might be the reason the pilot stayed in the closet. Why was he still looking for women on the dating apps? I wondered while I waited for a text back from him. I waited, and wondered. And continue to wonder.
