Three nightmare dates I wouldn’t wish upon anyone.

Third Time is Not the Charm

Queer dating can feel like a never ending scavenger hunt — equal parts possibility and awkward misfires, where bad dates teach you the ways of your heart (and what to avoid). But hunting for my person with the patience of a museum docent has only left me with a parade of disastrously memorable dates that feel more like awkward flashbacks than love letters.

Navigating Modern Love

I was raised with a script: get married in your early twenties, settle into a house with kids, dogs, jobs, cars. I pictured a tidy life — to-do lists and family photos — but two decades on, those boxes remain unchecked. I still love the idea of love but I’d rather be alone than settle for someone who isn’t my true match and who doesn’t see me as theirs.

Sometimes, I feel permanently single, even though I’ve been in a string of long-term relationships — mostly rocky, predictable cycles. I wonder if the right person will ever show up at the right time or if that moment has already slipped past me. Maybe it comes down to my “type.” I keep being drawn to versions of my first crush: a woman I met teaching in South Korea — smart, creative, tattooed, dark-featured, short-haired, with a magnetic face and an inscrutable confidence. Her energy pulled me in and I’ve been chasing echoes of it ever since. For more on how lucky I felt then, see how coming out changed everything — Come on Out.

Since moving to Chicago, though, sparks have been rare. Dating has slowed to a crawl and sometimes it feels nonexistent. So, I’ve nudged myself into the world of apps — a handful of platforms, open profiles, an open mind — waiting to see who crosses my path next.

Date Number One: The Fire Thrower

Lately, my weekends have been a blur of neon and laughter in Boystown, Chicago — late nights clinking glasses with friends, the kind of nights that stretch until the city breathes a little slower. At our favorite bar, there’s a woman who’s become part of the scene: same smile, same rhythm behind the counter, a small constant in a noisy place.

One evening, I mustered up more courage than sense and slipped my number into her hand. Silence. Weeks passed, the city moved on and then one night she was there again. She caught my eye and with a casual shrug, confessed my note had gotten wet in her pocket — which somehow felt both like an excuse and an invitation. Foolishly optimistic, I handed her my number a second time. Once again, nothing.

I drifted back to that familiar bar one ordinary weeknight — I only intended one drink but the night unraveled differently. Glass by glass, the room blurred into easy conversation. As I pushed toward the door, the bouncer waved me back with a grin and said I needed to speak to the bartender. I crossed the crowded floor, thinking it would be a quick word. Instead, she vaulted onto the bar, caught me by the cheeks and kissed me without warning. My friend stood frozen, mouth open, watching the scene with disbelief.

Let’s rewind a bit. She was extreme — even by my standards. Ink and metal covered her from scalp to soles; piercings dotted her face like constellations. She made a living throwing fire and, as I later learned, had split her tongue down the middle like a serpent. She announced she was leaving the state in a few days — this was her last hurrah — and I braced for a long, unpredictable night.

We drank until the world blurred and ended up at her apartment. I woke to the steady snore of her bulldog pressed between us and the morning light cutting through the blinds. She yawned, mentioned she was late for a meeting with her tax accountant and casually dropped that she had a girlfriend. They were in an open relationship. Fascinating — and absolutely not for me.

Date Number Two: She’s Complicated

Next, I decided to try dating offline for a change. There was one woman I kept spotting around town — always with the same companion, inseparable like a single entity. Figuring nothing would come of it, I befriended both of them and settled into months of polite, surface-level chatter.

Then, one night she arrived alone. She crossed the room with the kind of confidence that felt rehearsed, made a direct line to me and proceeded to flirt like she’d been waiting for the moment. We talked, drank and toward the end of the night we kissed while her friends watched with a mix of amusement and approval. I took a taxi home — sensible, at least — but our messages continued into the small hours. That’s when she dropped the reveal: she hadn’t broken up with her partner. Their relationship, she said, was “complicated” and she’d told her girlfriend she needed to “explore.”

Against better judgment, I saw her again on a weekday. She came armed with drinks and charm, trying to push past my reservations. In some alternate universe, I convinced myself there would be a clean break — either she’d end things or I’d walk away before it got messy. Neither happened. Her behavior felt increasingly callous and the more I learned, the less I wanted to be involved.

We eventually stopped talking. The part that still bothers me is that whenever I run into her now, she’ll call out to me as if nothing happened — her girlfriend standing right there, watching. They’re still together and the whole episode has become a reminder that sometimes the thrill of an encounter masks a lot of unresolved damage.

Date Number Three: The Sleepwalker

For my last attempt, I decided to try online dating — OKCupid? Tinder? The apps blur together. Either way, I matched with someone. Cute, a little younger than my usual type but composed and sharp in our messages. We agreed to meet for drinks on Saturday.

Saturday arrived. The conversation flowed, the laughs came easy and the bar did its magic. At the end of the night, she mentioned she lived outside the city, so I offered her a place to crash. We were both exhausted and called it an early night.

Around 3 a.m. a sound pulled me out of sleep. Half-asleep, I opened my eyes to see her hovering over my laundry hamper. I mumbled, “Are you okay? Need water? Bathroom?” She assured me she was fine, then I heard a subtle snap. Something about the movement felt off. Once she drifted back to sleep, I went to check.

My fingers met damp fabric. I sniffed. The smell hit me instantly. She had peed all over my hamper — every shirt, every sock, a soggy mess of dirty clothes. I hauled everything into the laundry, cleaned the floor with irritated, bleary-eyed efficiency, then crawled back into bed.

Morning came. She grabbed her shirt off the floor, wrinkled her nose and said, “Oh, it’s still wet from the rain last night.” No. Not rain. Not even close. She shrugged, slipped it on and left. I never heard from her again. Maybe she was too embarrassed to explain. Or maybe some awkward first dates are destined to end with a mystery no one wants to solve.