‘What’s the most awkward date you’ve been on?’ – 40 truly cringeworthy encounters
It’s a while since we’ve been in the dating game and we really don’t miss it.
Not just because today we’d probably have to join Tinder (rather than perusing the personal ads in Time Out).
But because in our experience the mostly great first dates (not many) were heavily outnumbered by the truly awful (quite a lot).
And these people’ memories of their awkward dates brought the memories rushing back. It all began when @NateIsBack2 asked this on Twitter.
What’s the most awkward date y’all ever been on?
— Steven Glansberg (@NateIsBack2) April 12, 2021
And we’ve read all of the replies (well, lots of them) so you don’t have to, and here are our 40 favourites.
1.
Her parole officer stopped by our table to say “hi” and remind her if she violated curfew again he’d send her back to prison
— Thomas Gillen (@ThomasGillen) April 13, 2021
2.
We went out to eat and she ate her steak like a taco. she folded it with her hands and ate it. No knife, no fork just vibes. https://t.co/BjFxXIdI0G
— the sultan of slut shorts (@AndrettiBX) April 13, 2021
3.
His family owned/ran a funeral home. Did not have an issue with that, but he spent the later part of dinner telling me what kind of makeup techniques he would use on me if I died.
— BIG Miss Steak 🥩 (@ba3thany) April 13, 2021
4.
When i was a teenager, this boy cooked me dinner at his house. It was lovely. Then his dad came home and told me about the terrible date he had. He described the woman and a few key details. I sat up straighter and asked the name of his date. It was my mom.
— 🌙 Megan Amato (@Vanahailey) April 13, 2021
5.
His tag was hanging out his top so I pulled it off. The look on his face told the story of a man of who had intended on returning that £350 T-shirt and no longer could. He didn’t smile for the rest of the date and I never heard from him again. https://t.co/oIOxay7m5S
— Slinging Seamoss ✨ (@Corey_jamesx) April 15, 2021
6.
He was older. Good looking but old enough to be my dad lol. We were sitting on the restaurant’s patio on these sofas having drinks. He wanted to take shots. I could tell he was lit so I was like nah. We took 2. I went to the restroom & came back this man was sleep on the sofa. 😭
— nae (@euphorixa) April 13, 2021
7.
The menu said the burger was served “Medium” he goes “nah I want it Large”. I explained that’s not what it meant but he proceeded to request a large from the waiter anyway 😣 https://t.co/MRCh1sG5BK
— annette abena #DiasporaTalks (@annetteabena) April 14, 2021
8.
On a first date I went on a sunset hike with this guy. On our way back down the mountain we get lost, phones on 1%, guy calls his mom who tells us to call 911. 911 sends a rescue team to walk us down. Next day we end up in the local paper
— pfizer pfairy 🧚🏾♀️ (@thatstelladoe) April 13, 2021
9.
Accidentally farted during a goodbye hug and she ghosted me afterwards.
— 🙏🏿 Ordained by Audacity 🙏🏿 (@FGod92) April 13, 2021
10.
I went out with this guy once and his transmission went out so he drive me home in reverse 🤷🏻♀️
— Squirtle 💦🌈 (@yellagirl02) April 13, 2021
11.
She invited me to the hotel, I’m like aight bet🤪🤪. I get there & it was a fucking Pyramid Scheme recruitment event 😭😭 BIIIIIITCH https://t.co/WsdBwWgbqW
— Coochie Dad (@dee_cisions) April 12, 2021
12.
We “bumped” into her pastor on our date and the man said to me “I sense in the spirit that there are demons tormenting you and they will never allow you to have a partner”. The girl went to the toilet and never came back. She’s married to the pastor now, I’m so happy for them.
— Sandile Nyati (@NdiniGC) April 13, 2021
13.
He spent almost 30 minutes complaining about women, and why they shouldn’t be in the workforce because they ‘take too many bathroom breaks’.
He told me he sat outside his office’s bathroom and TIMED women entering and exiting.
I stood up and left when he got to that part.
— Seitan is my co-pilot (@Melissa_Officia) April 13, 2021
14.
Motherfucker took me into a grocery store so he could use some of the deodorant. It was roll on. He didn't even buy it https://t.co/S4OeMRKrl3
— Beat People With Kindness™ ✋ (@calumydiahood) April 13, 2021
15.
Went to get wings with a man that was taking all of the chicken off the bone with his hand, balling it up, and then shoving it in his mouth. Man ordered like 30 wings… with the bone……………
— K@ (@Breathe_easyy_) April 12, 2021
16.
Got pulled over 10 mins in and he had a suspended license and no insurance. They towed the car and his mom had to pick us up. He offered to drop his mom off so we could go but I declined and had mom drop me off at my car.
— ♓️ (@__BRAT_) April 13, 2021
17.
After the date we went back to his place to chill and he had an eviction notice on his door.
— Paula’s Daughter (@ShaylaBGoode) April 13, 2021
18.
I went on a date with a dude who was a lot shorter then me. I’m 5’11 and he was 5’5. He asked me to step off the sidewalk and walk in the street so I wouldn’t make him look so short. He was dead serious. I actually liked him but never spoke to him again after that day.
— Ellzworth the Time Traveler (@elainesinsane) April 13, 2021
19.
hmmmm.
toss up between guy who told me (during appetizers) he thought ken starr was a good guy vs. guy who encouraged me to order dessert because “he likes women bigger than himself.” https://t.co/s1Wj8vlkWp— Monica Lewinsky (she/her) (@MonicaLewinsky) April 14, 2021
20.
He said we were going to an event his friend was DJ-ing at and it was a funeral 😭 I showed up in a party dress
— Liv (@Cholivia_) April 13, 2021