Dating Nightmares Come True

Illustrated by Sydney Hass.
We were two single women in our 20s, living in post-recession Brooklyn. So, life was just like all the TV shows would have you imagine: We drank a lot of cheap beer, complained about our jobs, and went on a lot of bad dates. A lot of bad dates. After what felt like a million of them — the guy who got a tattoo in honor of Emi and then stopped calling, the guy who tweeted @ his girlfriend from Jessie’s bed — we realized there was only one silver lining: These terrible dates made amazing stories. Thus, Bad Date Great Story was born. We started asking friends for their tales of woe, and the floodgates opened; it seemed that everyone had bad-date drama to share. Here are the best of the worst.
1 of 9
Illustrated by Sydney Hass.
Love The One You're With
"I showed up at the bar and spotted my date, sitting alone at a back table. Miraculously, he was not unattractive. We’d technically met the week before, at a party — but it was a dark party, and I’d been drinking, and my memory was foggy.

"For a minute, I worried I wouldn’t recognize him, but there he was! Score one for Anna vs. Beer Goggles.

"I walked right up to him and sat down: 'How are you? Saturday was so crazy!' He stared at me nervously. 'Yeah…it was…' he stuttered, seeming nervous. We ordered a round and made awkward small talk. I was actually relieved: He didn’t seem to remember the details of our first meeting. either.

"A few minutes later, someone tapped me on the shoulder. I turned around, glaring at the interloper. One look at his strangely familiar face gave me a sinking feeling. 'Anna?' he asked, uncertainly. I looked back at my date. Come to think of it, he didn’t look much like the guy I had met at the party. Which made sense, since he…was not that guy.

"I apologized and switched tables, mortified. To my actual date’s credit, he laughed — but his eyes shone with a look that either said, ‘Haha, you’re quirky,’ or possibly ‘Haha, you should consider rehab.’ There wasn’t a second date."
— Anna Moreno
2 of 9
Illustrated by Sydney Hass.
Break A Leg
"I never anticipated being a single man in New York City — I’m a self-proclaimed 'nice guy' from Oregon — but lo and behold, there I was, online dating in the Big Apple. I met Vicki on OkCupid, and we had enough chemistry that after our second date it seemed we would wind up back at my place.

"We were crossing the street after dinner when bam — we got hit by a cab. I slid up the windshield and onto the roof, and landed with shocking grace, somehow avoiding injury. Vicki was not so lucky; she broke both her kneecaps. I rode with her in the ambulance as she listed all her medications ('Don’t listen,' she said. 'The birth control is the only one you should care about.') I felt so terrible that for the rest of the week I went with her to her apartment and carried her up her four flights of stairs. One night, a few men came by to purchase her opiates. I knew then that Vicki and I were not meant to be.

"But, I will see her again; I’m a witness in her lawsuit."
— Nathan Smith
3 of 9
Illustrated by Sydney Hass.
Everything Was Going So Well....
"One summer in late high school, I convinced my parents to let me skip our family vacation so I could go see my best friend who’d just moved to another state. I arrived at his house late, after his parents had gone to bed, and produced the housewarming gift I’d brought in my bag: a plastic water bottle ¾ full of cheap tequila.

"Here, I should clarify: This was not just my best friend. This was my best friend whom I was more than a little in love with, and fully intending to lose my virginity to — ideally that very night.

"We drank the tequila, moved up to his bedroom, sat talking on his bed — and then, in a moment of drunken courage, I kissed him. And, holy shit, it was all happening. Shirts were off, I was on my back, he was taking off my pants. I remember leaning back and looking at the ceiling and, for a brief second, thinking, 'Man, this is going so well,' before, in the grand tradition of tequila-drunk high-school kids everywhere, he threw up all over my chest.

"I showered, and we actually made a half-hearted attempt to pick things back up again. But — half as drunk and twice as awkward — we couldn’t get things going."
— Nick Tern
4 of 9
Illustrated by Sydney Hass.
The Little, Red Flag
"The actual date was great — maybe we drank a little too much vodka, but it was good fun. The bad part happened the next morning.

"I woke up before him and got out of bed, deciding I’d borrow one of his cool All Saints T-Shirts. I threw open his wardrobe, and at the bottom of the lowest shelf was a red dildo. I thought, 'How fun!' So, of course, I pulled that sucker out and started using it like a wand from Harry Potter over his lifeless, sleeping body. He woke up…and started to freak out.

'Put him down!' he said. 'Put him down!'


'OK,' I said, dropping the dildo. 'What's the big deal? Also…why him?'

'He’s a mold of my ex-boyfriend’s penis. Don't touch!'

I slowly wiped my hands on my underwear. And then: 'His name is Little Red,' he said.

"Sometimes, a red flag is literally red. And, shaped like a penis."
— Mike Kelton @mikekelton
5 of 9
Illustrated by Sydney Hass.
Better Late Than Never
"I met Chris on OkCupid. He was charming, handsome, he got along with my dog, and he wanted a long-term relationship. By the fifth date, I thought: It’s time for the sleepover. I invited him to my place for a home-cooked dinner — and spent hours preparing. I seared tuna steak, sprinkled salt on edamame, and poured wine.

"He was supposed to arrive at seven. Seven came. Eight. Nine. I called his phone, and it went to voicemail. Just like in the movies, I finally blew out the candle and cleared his plate…when someone knocked. I opened the door, and there was Chris — wasted. Apparently, he had been 'nervous' about the overnight, so he stopped by a bar on the way over... and stayed for nearly three hours.

"When I told him I thought he should leave, he picked up a couple pieces of edamame and flung them at me (I think this was supposed to seem playful?) I told him I was going to walk my dog, and that when I came back, I wanted him gone.

"When I returned, he was passed out on my couch, bundled in a blanket — a complete dead weight. I let him sleep it off and went to bed. By my dog’s morning walk, Chris was gone, never to be heard from again."
— Addie M.
6 of 9
Illustrated by Sydney Hass.
Too Stoned To Function
"After a tough breakup, my previous no-strings-attached-sex-buddy resurfaced in my life, coincidentally around the same time I resurfaced from lying on my floor with pizza. He invited me to come by a party he was having. Excited to break my dry spell, I threw on some lipstick and went out for the night. I arrived around midnight, but determined to stick around for some breakup-erasing sex.

"Eventually, someone suggested we smoke a little pot. I took a hit, tried to pass it, and then took another hit. A few minutes later, I realized I was the only one smoking — and that I was absurdly high. I looked up to realize the guy I’d come to hook up with was sitting about 15 feet from me.

"In a fever state of weed, I decided to text him to see if a hook-up was still on the table. It was not. (In retrospect, this may have had to do with the fact that I was texting while also clearly staring at him.)

"After a near-eternity of sitting in silence, I needed an elegant exit strategy. I landed on awkwardly yelling, 'Thanks!' and running through the party, out the door, and into the night."
— Alison Leiby, @AlisonLeiby
7 of 9
Illustrated by Sydney Hass.
The Perils Of Online Dating
"New to NYC, I decided to try online dating. Despite my friends’ warnings that Craigslist wasn’t the spot to do that, I went straight to the Women for Women section and found what I felt was a jackpot post: 'MODEL who can’t find someone to respect her intellect.'

"Perfect! I could definitely respect her intellect!

"After a few email exchanges, I was convinced this was the real deal and agreed to meet at a 7-Eleven in Queens. The location was her choice, and I just figured it was a secret model hangout. Assuming she was doing intellectual-model things, I didn't mind TOO much that she was almost an hour late (all that modeling and reading must be hard).

"Except, when she showed up, she looked nothing like the person in her picture.

"Her opening line — 'I look like this because I just had dental surgery' — made no sense (dental surgery on your whole face?), but since I didn’t really know what else to do, I nodded and followed along on our date.

"At the bar, she proceeded to tell me about her failed acting career (I didn't bring up the modeling) and asked if I liked to party. Before I could respond, she took out a bottle of pills and swallowed a couple. Full to the brim of naiveté, I asked if the pills were from her 'dental surgery.' She just looked at me, confused. At one point, she noted drunkenly, 'If anyone comes over, pretend we met organically!'

"I took a moment to think how sweet it was that she was imagining a future where we lied to make our meeting story sound more romantic…and then, I fled."
-Emma Willmann, @emmawillmann
8 of 9
Illustrated by Sydney Hass.
Under A Bridge Downtown
"Months after extricating myself from a nine-year relationship, I jumped head-first into online dating. Date One was with 'Musician Guy,' who asked to meet at a 'really cool bar' in a part of Brooklyn I didn’t know.

"I exited the subway into the most desolate area of the city I've ever seen — totally abandoned. The few people were all gritty types, and none were alone. But, I decided this wasn't necessarily a dangerous neighborhood, just up-and-coming. Who knew, maybe it’d be next-generation hipster in a few years.

"Unfortunately, even Verizon didn’t know this part of Brooklyn — leaving me without a way to look up directions, or let the guy know I was late. After a sketchy 30 minutes of wandering under a bridge, I gave up and headed back to Manhattan, mecca of safe streets and cell service. When I finally messaged Musician Guy to let him know what happened, he responded: 'Oh, yeah, the best part about that place is that it's unmarked. That's why it's a neighborhood secret.'

"Pro tip to hipster daters: If the bar is unfindable, your date may not be able to find it." — Jessica Bach
9 of 9
Illustrated by Sydney Haas.
Fool Me Once...
"I met Peter at the hospital where I was a doctor. When he asked to get dinner, I was resistant. In addition to being seven years younger than me, he didn't have much in the personality department. But, when you spend the day in a psych ward, boring can be, well, exciting — so, I agreed. "After drinks, Peter asked if he could walk me home. At my door, he went in for a kiss, which I diverted, so we ended in an awkward cheek-rub. As I turned to go inside, Peter asked if he could use the bathroom. 'I have a long subway ride home,' he said. So, I let him inside, thinking I had safely diffused any sexual thoughts.

"I was wrong. After a pretty long wait, Peter swung open the bathroom door — stark naked.

"I stared at the pale, hairless body of my co-worker. 'Put your clothes on!' I screamed. Clearly embarrassed, he went back in the bathroom, put his scrubs on, and left.

"Amazingly, a week later, he asked me out again. This time, I declined."
— Alex Green