Twitter Users Ponder the Most Awkward Dates They've Ever Been On

Look, I really do like to write an at least vaguely related preamble before these social media roundups. My day job has expanded into my evenings and weekends and is not giving me very much time write or think about writing at the moment, so these short bursts are always fun to do as they keep the writing muscles limber and serve as a nice brief break by taking me away from my other concerns for a few moments. I like writing the segues. I get to feel like a cheeky court jester with a twinkle in his eye as he presents to the court the latest mad sh*t he’s seen while prancing around the kingdom. It’s fun. Sometimes I don’t really have time to do even that though. Other times I’m left so stunned by the content of the roundup I’ve prepared that I’m actually a little bit hard pressed as to how I could possibly segue into what’s to come.

Today is one of those times.

Twitter user Steven Glansberg posted this prompt two days ago:

What’s the most awkward date y’all ever been on?

— Steven Glansberg (@NateIsBack2) April 12, 2021

And, well, as you can imagine, the pickings were rich. I genuinely cannot think of a way to lead into a piece that contains some of the stories below. So I’m just gonna let the responses speak for themselves.

Because there’s ‘awkward’, and then there’s some of these:

Shortest date ever. He picks me up, I get in the car & he compliments me on my hair. Then he asks if it’s real 😑 when I decline to answer, he turns on the interior light & starts inspecting. “Wait, turn your head let me see” SIR!! You know what..this ain’t gone work. Good night

— ginger & spice (@so_antisocial) April 13, 2021

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

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

He was late, rude, and then asked where my sister at, since I wasn't having a good time. He told the waitress to split the bill, he had drinks and a appetizer. I had water. I stormed out front of his bar friends (he was a regular there).

He had a newborn that same night.

— Jay-Z's Long Lost 92 Bricks 💵 (@TJ_Paperstacks) April 13, 2021

She was obviously not girlfriend material, me and my boyfriend fart at each other all the time 😂

— 🌿✨🌙 Yþgeƿinn 🌻✨🍂 (@sladeofyaupon) April 13, 2021

girl took me back to her place, kept disappearing and arguing with her unseen roommate in the other room about how she's being a whore for having me there.

…but she didn't have a roommate. She was arguing with herself.

— Dominic Biondi (@DominicABiondi) April 13, 2021

I went back to this girls house after drinks and found out she had a giant pet pig… then the pig bit me when I went to pet it
She scolded it like a dog and put it outside.
Then a cat sat down in front of me that looked like Theodore Roosevelt and just stared at me…

— Stu Tube (@MaddenG0d24) April 14, 2021

We met and I noticed he was super quiet. To fill the silence, I just started talking about randomness.. anytime I asked him a question, he would awkwardly laugh and look away. He texted me 30min into it and told me he was deaf and heard nothing I said… pic.twitter.com/H2cYWVrScZ

— Kay 🙇🏾‍♀️ (@O0hkay_) April 13, 2021

I went out with this guy once and his transmission went out so he drive me home in reverse 🤷🏻‍♀️

— Squirtle 💦🌈 (@yellagirl02) April 13, 2021

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

One of my first dates with a dude who had a python. I went to the pet store with him, picked out the mice. He smashed them on the wall, but I fed them to the snake.

No 2nd date because I didn't freak out over the mice or snake. He said I was "too manly". Loser.

— Anika (@faboomama) April 13, 2021

Basically we went out and she was a klepto and a pyromaniac and when I caught her stealing she made you like this whole huge deal about it and legit tried to storm off while I was apologizing to the owners she set a fire and got the fuck on

— Marley (@strange_insane) April 13, 2021

When I tried to kiss her at the end and she said "No!" because "Nothing would come of this…"

I reminded her of this a few years later when our daughter was being born. 😐

— The Foncé 👍🏿😷 (@ChocnessMonsta) April 13, 2021

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

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……………

— [email protected] (@Breathe_easyy_) April 12, 2021

We were sitting in a park and her husband threw his sandal at us.

— steven (@steventuality) April 13, 2021

That he doesn’t even wear to court (attorney). He arrives in a ROYAL BLUE SUIT made of inferior material & NOT tailored just big & baggy & matching gators. NICE restaurant & he keeps snapping his fingers & loudly calling the waiter “garçon”😭. He’s a bit older than I am so we got

— Viscountess Vacciné (@BelleRideaux) April 13, 2021

Back to my hotel and ALL OF A SUDDEN he’s too sleepy & drunk to drive home. I make several suggestions of OTHER places he can stay, but he seems to knkw through telepathy that they’re all booked😐. He finally gives up but runs to his car to get a gift for me. He’s had a plaque

— Viscountess Vacciné (@BelleRideaux) April 13, 2021

He still wanted to be friends though🤣 I wanted out of my old college car & his buddy owned a ☮️dealership. He worked w/him to give me a great deal & lots of free upgrades on a brand new,current yr model even though my college 🚗 I traded in was only worth like $700 LMAOOO. pic.twitter.com/kjMloA04Vl

— Viscountess Vacciné (@BelleRideaux) April 13, 2021

Not a TERRIBLE trade off for a couple of hours of weirdness. He actually was really nice to me the whole time, just uncouth🤣 & the the food & the show were great 🤣.

— Viscountess Vacciné (@BelleRideaux) April 13, 2021

One of many…
In the middle of our 2nd date I asked him why he was moving to the area, he said that he had accidentally shot his wife (who was sneaking back in the house one night from cheating) and needed to get away from the media surrounding it.

— Ashley Jane (@janericbrand) April 13, 2021

We were at her place, shes cooking (she was cooking a Nigerian dish) and I was leaning against the wall. I looked over my shoulder and saw a roach trying to high five me. I got up and she said and I quote, "stop acting like a little girl, it's just a bug."

— Meh😒 (@meh_linmusclan) April 13, 2021

Dudes mom came up to question me before he came out (first time meeting him). He took me to a bingo hall, then made me stop at the store so he could buy a STACK of scratch tickets.. we scratched them & he went through each individual ticket and pointed out all my mistakes.

— big daddy simp ✨🤌🏼 (@littleredromi) April 13, 2021

Second date. Pro skateboarder. Really cute. Friends with my friends. We made out but something about how he kissed me freaked me out. I gave him a fake number. Years later he killed his girlfriend.

— Patricia Arquette (@PattyArquette) April 13, 2021

Not the "most awkward" but I should have known we wouldn't last long when he snatched the last piece of bread from the bread bowl that I was reaching for and reminded me that I had said earlier in the date I was starting to work out more.😒

— Alejandro (@AlejaEtcetera) April 14, 2021

I, a music person, got in his car. There was some light conversation & then silence. So i said “you gon play some music ?” & he says to me “oh i don’t really listen to music.”

I’ve just… never met someone who doesn’t listen to .. music ..??????????

— Khalil (@kbyrd2_) April 14, 2021

Went on a second date (mistake). We watched The Color of the Cross (Google it please). *I* thought it was hilarious, he took it dead seriously. When we got coffee after, he kept looking at me and saying he knows he's in love with someone he just needs her to realize it too

Me: pic.twitter.com/jS6HioLP4h

— DW McKinney (@thedwmckinney) April 14, 2021

Not just one date ~ I married him.
Together 1 year and proposed. When we got married we were together almost 2 1/2 years.
Married almost 1 1/2 years and I’m at work and get a text message from a woman asking me how I know her husband 😳there were 3 of us. He’s a licensed Atty

— mamabear4445 #VOTEandWearADamnMask (@newlotus) April 13, 2021

he tried to convert me to Christianity. even after I explained that I was happily atheist, he kept telling my why I lost faith in god and why that needed to change. also told me multiple times how he could tell how much I liked him. welp… I full-on holy ghosted him 👻

— Kelly 4 Dayz (@kjxoxo) April 14, 2021

Went on a date with a college classmate.

After our food came out, a goddamn knife and meat cleaver fight broke out in the kitchen that spilled into the dinning room.

I spent the rest of the evening wondering if my date was trying to get me killed! 😶https://t.co/uemBcvsjXH

— 😷 Caleph B. Wilson (@HeyDrWilson) April 14, 2021

It’s quite a long story but short version is he said his childcare canceled last minute so brought his son and said had to go back to his place for a sec and would I ride along. Get there, then he disappears to go “buy diapers” and I was stuck with his toddler for 2 hours.

— The DarkSkin Duke of Panoramic Thigh Meats (@wordsbyuchechi) April 13, 2021

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

I worked for the AHS and toted animals in my car. For a first date, I cleaned it thoroughly, picked up my date, turned on the air, and the car filled with a storm of hair. She smiled at me. 42 years, 4 children, 7 grandchildren, and countless mistakes later, she still does.

— Michael Murphy (@Michael44250089) April 13, 2021

Dinner date, while waiting for our food to come out his gf shows up yelling at him. I left them to beef it out but was still hungry so I went to the server to ask for my meal togo. Server saw what happened & let me take both meals home. went home to watch a movie and ate good 😁

— Val (@EcuadorianVal) April 13, 2021

A dude who showed up late, talked incessantly about topics I could’ve contributed a LOT to had he ever let me speak. About 45 minutes in he said “so what do you like to talking about, hair?” & I said “not usually with a bald man, no”. I ended it pretty abruptly after that.

— Jennifro (@Jennifro1) April 13, 2021

I walked in and the guy said, “I must have been drunk.”

He also kept asking if HE physically gave me his number or one of his friends.

And through the rest of the date he just kept shaking his head saying, “I had to have been drunk.”

— Tiger Ray (@TigerAJRay) April 13, 2021

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

He spent a huge chunk of the dinner at a well-lit restaurant giving a long, clearly prepared, speech about how beautiful my brown eyes were and how he couldn't stop thinking about them.

My eyes: pic.twitter.com/tpFMPg3wd2

— fry (@anniefryman) April 13, 2021

Probably the first date where we ordered dinner and then, after I said my girls were already grown and I didn’t want to have more children, he asked when he could get me pregnant

— Jeanna Kelley (@jeannathomas) April 13, 2021

i took a guy out on a date and i offered to pay for his food and drinks, and then after i paid for everything, he asked me can i pay to get his ps4 fixed, or if i can buy him a ps5. its up to me… 😒😒😒

— Jiggly Puff🐽💕 (@chai_bleu) April 13, 2021

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

Was stood up on a Saturday then opened the paper Monday morning to find he had decided to murder his poor ex instead. He'd killed her then dropped their toddler onto a commuter train unaccompanied then had a police stand-off. Still in prison to this day 25 years & counting.

— Ruthy Hope (@_Nefertitties) April 14, 2021

To be fair, that sounds hilarious.

— Calypso's Daughter (@Sweet_Sour_Tang) April 13, 2021

Guy I was set up with blew the n-word as I sat down at the table.

I conspired with a server to sneak out the bathroom, she had a guy walk me to my car. I came back two hours later and bought a round for the staff I could not afford.

— Beth Schacter (@bethshax) April 14, 2021

Ah. Love this question. I call him Shirtless Wonder. He took off his shirt in the middle of dinner & started flexing his pecs….and staring down at his pecs each time. I think I left skid marks in the driveway when I left. The story is longer & weirder, but this is the gist. 🤣

— Sandi (@Sandals2112) April 13, 2021

Great looking. Very successful. Picked a great spot in San Francisco. Conversation great…until he said, “What are the chances I’m going to have anal sex tonight?”

My response: “Well, I can’t speak for anyone else in here, but with me 0%.” And, I picked up my purse and left.

— Harry’s Mom is Vaccinated! (@HardChick18) April 14, 2021

toss up between the guy who showed up in sweatpants and a Fanny pack and then fell asleep, or the guy who told me I looked like his brother with longer hair

— Chairman Birb Bernanke ♡ (@Bonecondor) April 14, 2021

He asked me what kind of food I liked. I said Italian. So we went to little Italy.
Him: "I don't really like Italian"
Me: oh
Him: oh… they got chicken Parmesan? I love that!
Me: but that's…Italian?
Him: is it?

— ThisIsRochelle (@RR416) April 14, 2021

Went on an eharmony date. My date shows up, says hi, sits down, looks me up and down, gets up and says “yeah I can’t do this” and walks away. The waiter felt so sorry for me, he got me a free meal. Found him on FB years later. He’s gay 🤷🏽‍♀️

— Sara Roselyn Reiter (@SaraReiter) April 14, 2021

I (briefly) looked a bit like Christopher Reeve while I was in college. A gal asked me to a dance, and we went to her dorm room with a few other couples for drinks. Every wall had a Reeve/Superman poster, including the ceiling. Ran away….

— PappyFitz (@PappyFitz) April 14, 2021

She shared a house with 2 male roommates, and between them they had 1 fork. The whole date, I kept wondering how they rotated the fork between the 3 of them. To this day, I still think about what happened to the other forks, and why no one thought to buy more forks.

— M Coyle (@elyocttam) April 14, 2021

He asked me to help him move “it’ll be quick!” before our 2nd date downtown. I said yes cos I was 22, ended up miles away clueless how to get back. Got to his apt & he hadn’t packed a thing & while he packed I quietly left & he drove by shouting “you’re going the wrong direction”

— Quintin Marcus (@quintinmarcus) April 14, 2021

Drinks & dancing were great, but when we got back to his apt he pulled out a suitcase full of magic tricks. Already slightly unsettled, he showed me a few & the last trick he made his thumb disappear. Asked him how he did it. He was just missing his thumb.

— Alecia Wallingford (@alecia_wall) April 14, 2021

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

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Petr is a staff contributor. You can follow him on Twitter.

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