Reflections on a Date Gone Wrong

Treena Orchard
The Chorus
Published in
6 min readApr 9, 2020
Photo by Skyla Design on Unsplash

Like almost a billion people on the planet, I’ve used dating apps to navigate the lottery of longing that is modern romance. My journey through the sordid terrain of digital dating came late in my life and in actual time. I didn’t use an app until 2017 at the ripe yet desirable age of 45. Before I learned to better protect my heart and hopes, I fumbled.

After swiping for a couple days, I stumbled upon a profile very different from the rest. Instead of one or two badly staged pictures, his were professional, with a photographer’s name along the bottom in a classy, modern scroll. His profile was well-written, another departure from the usual pattern in appland: writing nothing, sounding cautionary warnings that they’re “new on here,” or proudly stating that they own a car and have a house.

When I began swiping for love-lust, I was newly single and nervous, which made the idea of meeting in public a little daunting.

I leapt at this shiny prospect. In the blink of an eye he responded with his phone number. And with that, we were texting like mad; in less than a week we exchanged over 1,000 texts. We hatched a plan for the coming Friday: sleepover date at my place. Why? He lives over three hours away and wine will be had.

More than anything, we arranged to meet at my place because it’s where I feel safe. I live in an art-deco building with walls so thin when the guy upstairs goes pee, it’s audible. Should anything go wrong, people would know. When I began swiping for love-lust, I was newly single and nervous, which made the idea of meeting in public a little daunting.

Who was this person standing at my door? Cropping and editing can only remove so much from the frame.

As the week came to a close, I tried on several outfits, which I duly photographed and solicited feedback on from helpful friends. It was decided that I would wear a flowing skirt with a blouse tucked in to tastefully show off my backside, along with some nice jewelry and minimal make-up. On the night in question, I busied myself preparing dinner. He texted me when he left his place and sent cute messages the closer he got, including a sailboat emoji and the message “smooth sailing.” I was checking myself in the mirror every three seconds and literally jumped when I heard the front door buzzer.

But there seemed to have been a mistake because the nervous person I saw through the leaded glass of the foyer bore no resemblance to the attractive, confident man in the photos and the texts. Who was this person standing at my door? Cropping and editing can only remove so much from the frame.

Could I see how women could love him and find him desirable? What kinds of women have loved him, I wondered?

As I made dinner, I glanced at him out of the corner of my eye, trying from as many perspectives as my optic design as a human would allow to make sense of what I was seeing. I was trying to assemble the pieces of a disappointing puzzle that was coming apart before me. If I looked hard enough, could I see the hot guy in the picture? Are you in there?

Could I see how women could love him and find him desirable? What kinds of women have loved him, I wondered? I found myself comparing him to a fun-house mirror, which reflects illusions. He departed in every way from the ideas I had constructed. Was I communicating with two men, the guy inside the photo and the one pressing letters on a phone? Which one was leaning against the arch of my kitchen, anxiously gulping red wine and talking about his exes?

As we ate, I hunched over my plate of mixed green salad, pasta, bread, and butter. He talked about multiple long-term relationships and limited dating experiences. I decided not to share my sordid romantic past. Would he even care? Would I care if he cared?

I felt responsible for this man who came a long distance to see me and was now unable to drive home safely.

I continued to listen and wonder what the other women look like. I also wondered what he thought of me because he was asking few questions while looking to me for reassurance.

After dinner we retired to the couch, where I perched on the far end and prayed for it to be over. He kept asking, “Are you okay with me being here?” He was asking the right question but I was no closer to being honest and asking him to leave. I felt responsible for this man who came a long distance to see me and was now unable to drive home safely. Where would he go? Wouldn’t I be a bitch for kicking him out?

Although misplaced, these concerns overrode my desire to end this tragic date. Subsuming my own needs was an old strategy and women are typically raised to put others first, especially men. His less than jubilant body language let me know that he wasn’t entirely pleased with the situation, yet he too remained quiet about calling it to an end. Talking about power, desire, and failed expectations is not easy.

As I lay in bed the next morning, I was full of questions.

A few more minutes of useless conversation dripped by. I said I was tired and made my way to the bedroom, which was transmitting the weakest sexual pull ever experienced during a date. The journey from the living room and down the hallway felt like a perfunctory exercise of shutting down the apartment: Lights, check; quickly change into track pants and t-shirt, check; quietly ask my cats to save me, check; climb into bed beside unwanted stranger, check.

We watched a documentary on his iPad about climate change and how glaciers are “calved” or break off into the sea. Calving is both natural and destabilizing, as is laying stiffly beside a potential mate. He got up and moved to the couch.

As I lay in bed the next morning, I was full of questions. What will I say to him? What is he thinking? I heard the floors creak in the dining room, which catapulted me from self-reflection into action. I saw three options: appease the stranger sexually and then show him the door; limp through the morning; or engage directly with him, admit defeat, and bid him adieu. While option three was clearly the best choice, I went with number one. One date doesn’t change old habits.

I listened for the sound of his truck going over the concrete bumps on the driveway, the same sound that registered excitement a mere fifteen hours ago.

Following those hasty, tepid few minutes, it was time for coffee. I couldn’t get the French press going fast enough. When faced with an unsteady stranger in these conditions you simply can’t predict what will happen next, like when he proceeded to discuss tales of friends’ STI diagnoses.

Friends, you say? Gonorrhea, you say? I laughed and wanted to ask him, “Are you insinuating that I ‘gave’ you an STI (it’s always phrased in the form of a gift- ‘I give you this infection’!)?” Instead, I send more than a few SOS texts: “What to do? Sinking very fast. Help me. OMG. I think he’s leaving. Will report back asap. Over and out teddy bear.”

The texts proved unnecessary, because he had a work emergency, which he proved by putting his phone on speaker. I led him to the door and attempted a hug. I listened for the sound of his truck going over the concrete bumps on the driveway, the same sound that registered excitement a mere fifteen hours ago.

I leaned against the kitchen counter, reeling. Then I reached into the fridge for a secret. In anticipation of this date, which happened to fall on St. Patrick’s Day, I had purchased two huge chocolate cupcakes with green icing, sprinkles, and plastic shamrock rings. Bought to mark a festive occasion and perhaps a sweet connection, I ate them myself.

This essay is part of a series about relationships, dating, and friendship, sponsored by Chorus, the matchmaking app where friends swipe for friends.

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Treena Orchard
The Chorus

A prairie girl who became an Anthropologist who became a writer.