The world of dating is inherently awkward at times, which makes any mishap the occurs that much more mortifying. This is a concept the following people know all too well, as they recount the most embarrassing dates they ever went on.
Yeah I’m Listening…
“I was exhausted from a sports competition and from staying up all night on guard duty. At one point, when she was telling a slightly longer story, my head just fell backwards and I fell asleep with my mouth wide open. I might’ve even drooled a little bit” (Source).
“We’ve gone to the movies, had a good time. Afterwards… Her: Well, think I’ll call an Uber. Me: Hey, I can take you home, no worries. Her: You don’t have to… Me: (without thinking much) No problem, your place is on my way home. (moment of silence) Her: But you don’t know where I live. Me: Well…” (Source).
Get Out Before It Blows Up.
“I met a woman on an Internet dating site. She said she was single. Being a little flush with cash, I thought a good first date would be taking her out to dinner. Somewhere in the middle of dinner – her husband (with several business associates) came in and the hostess sat them at the next table to us. I walked out before they came to blows…” (Source).
An Unexpected Attack.
“I had met a beautiful and friendly Asian woman and we went out for coffee and dinner and then set up a date to go hiking in the Blue Hills. This was very fortunate for me since I have hiked the Blue Hills all my life and knew all the best scenic (and romantic) spots along the trails. On the day of our adventure we started out. Unfortunately, about three quarters of the way up the hill, in the middle of the woods I suddenly was overcome by diarrhea. Uh oh. I didn’t pack toilet paper for our two hour hike. And what was I to do?
I asked her if we could take a short break, then told her I had to pee and went running off into the bush. I ran and ran, as far as I could go so I could be invisible – and far from hearing (or smelling) range. I just made it behind a log and was relieving myself with great satisfaction and relief only to discover I had squatted next to a trail. To my dismay, a family with small children happened by. The young boy, who had raced ahead of the family asked me what I was doing. All I could do was hide my head in shame as they passed in silence. And I still had no toilet paper. I had to undress, take off my underwear and use it, and discard it, then dress again and go and find the girl.
I had been gone for some time. She looked at me with some questioning look but we continued onward. I didn’t know what the hell I would do if another attack took me. Use my hiking socks, I guess. No romance occurred and I never saw her again. I don’t know if she knew what was up but she displayed no further interest in hiking or dating after that. Maybe I smelled badly, who knows” (Source).
No Second Date.
“I was out on a date with a new girlfriend when we bumped into my very attractive female friend. And at the moment of introducing them, I suddenly found I was completely incapable of recalling either of their names. Needless to say, there was no second date” (Source).
“So, I play in these coed rec sports leagues, right? Right. One time, a few years ago, I met a really pretty lady on OKCupid and we had hit it off well and we were set for a date on a Saturday night. At that time, I happened to be playing in a dodgeball league that plays early on Saturdays, so I had a noon game, then I went to the bar with the team ‘for a few drinks’ LMAO.
Five hours later and I am s–tfaced after all the beer pong and flip cup you can imagine. So I finally am like ‘Wait I gotta get home and change and get ready for my date!’ So I do just that. I go home, I shower, I clean up really nicely, put on a very stylish blazer and this awesome silver shirt I used to have, I am READY BABY. Except I am still drunk. So, so, drunk. So here I am, at dinner with this gorgeous grad student, and we’re talking, and then, and THEN….
I throw up. Right there, in the middle of the restaurant. Right next to her. She’s mortified. I’m REALLY mortified. I wanted to just crawl up in a ball and cease existing. I am still drunk, but I can feel the heat in my face caused by the booze being replaced by an entirely different sort of heat in my face- that of absolute, all consuming embarrassment. I am blabbering out OH MY GOD IM SO SORRY OH MY GOD OH MY GOD PLEASE I AM SOOOOOO SO SO SO SO SORRY. Needless to say, I did not see this woman ever again” (Source).
Scaring The Cabbies.
“I met a girl in a bar and we hit it off. After a few drinks and some flirty conversation we ended up back at her house. We went to her bedroom and started to fool around in the dark and I spent some time going down on her. We had sexy sex and when the sun began to come up I told her I should probably call a taxi and head home. This is where things got strange.
When the taxi pulled up I popped my head in the window and the driver just screamed something at me and drove off. I was perplexed by his reaction but just assumed it was his issue and not mine. I called another cab which arrived quickly, this time I jumped in and the cab driver looked at me with these large saucer eyes. He took down my address and off we went. I tried to have a chat with him but he just wasn’t interested and kept shooting me these nervous furtive glances.
It wasn’t until I arrived home that I worked out what had happened. The girl I had hooked up with was on her period and she hadn’t told me, I’d gone down on her and came away with blood all over my face. To the cab drivers it must have looked like I’d tried to kill somebody by literally eating them. It was disgusting, and hilarious at the same time” (Source).
Conflict Of Interest.
“I went on a date with my ex’s boss once. Neither of us realized it until my child called. When I flashed my phone at my date and said I had to take the call, he looked a little confused. When I got off the phone, about a minute later, I apologized and said ‘Sorry about that. It was my son, I thought it might be important.’ He had a funny look on his face and said ‘So…___ is probably not a common name, huh?’ I just looked at him and he said ‘So I’m pretty sure I’m your husband’s boss. Dating someone going through a divorce is fine, until you realize you work with their spouse.’ After that date, I realized he was friends with my ex on Facebook and had told my husband his wife was too hot for him on at least two different pics of us together” (Source).
The Transforming Pants.
“I am 47 years old and this happened, so, embarrassment knows no age limit! First date with a man I’d met online. We decided to go see a movie. While he was picking up snacks, I was about 20 feet away and I glanced down. I’m wearing my favorite black leggings, a flirty bell sleeved top, 3? black boots and a Scottish wool shawl.
WHY I DO NOT KNOW – but I looked down and saw some ‘fuzz’ on my leg. I pull on it. And oh yes, if you’re a woman reading this you know I’ve made a fatal error. I pull and the string gives away along with the entire inseam of my left leg. I’m standing in the middle of the busy movie theatre. THE MIDDLE! And the glowing color of skin is now showing the entire length of my leg!!!! I panic. My tongue goes numb and I literally start turning in circles like a dog chasing her tail. ‘WTF do I do????’ I’m repeating over and over. In a circle. My date has finished his purchase and comes up to me. My eyes are the size of saucers. I can’t speak. He says ‘Ready?’ I can only nod. So, I walk with him to the theatre as if my legs are webbed together. We sit. Thank God I think – dark theatre now – I’m good!! Oh no. I sit down and the action causes a reaction. I can feel the separation of the cloth travel like the lit wick on dynamite. It shoots up the left thigh, across my YaYa, and STRAIGHT down the other leg!!! ‘Holy F–k I am literally losing my pants !!’ I’m thinking ‘how are my pants even staying on my body!?? WTF am I going to do??? I’ll have to live here in the theatre until no one is around but I have no car so I can’t slink home in shame! F–K!’
So, after the movie, that I did not watch, my date says ‘Let’s go have a drink and a bite!’ Oooooommmmmmmgggggggg I say to myself while ‘OK!’ comes out of my mouth. He just foiled my drive-home-and-run-away-fast plan!!! At this point, the only reason my pants are on my body is because of the waistband, the outer seam, and the fact they’re tucked into my boots. I was essentially wearing a skirt with no front. I’m laughing at this point. I guess the good side of being 47 is that I am accustomed to embarrassment, humiliation and crisis. Plus I was in the Peace Corps so I know how to improvise. And I want a drink! So, I take off my Scottish wrap and make it a skirt. Tied it right around my waist and went forth To imbibe. Which we did. AND My date NEVER noticed. Keeper? I think not” (Source).
Bested By The Little Sister.
“I had the most embarrassing thing happen to me ever when I first brought my gf to my house when I was 18. My little sister (15) was 6 inches taller and she was stronger. My gf and I were watching a movie on the couch. My sister walked by, then my gf asked ‘How old is your sister?’ I had to sheepishly say, 15. She laughed out loud, and said ‘But she is so much bigger than you!’ I was really embarrassed. But things got much worse. My sister and I got into an argument, and she started to tackle me and she had me pinned down within seconds in front of my gf. My face was facing the floor as she was sitting on me. She said in order for me to let her go, I had to say ‘You’re my big sister.’ I refused. I tried to get up a couple times, but she held me down with relative ease. All I was thinking is how sad it was to be beat up by my LITTLE sister in front of my girlfriend. To make matters worse, she then started talking with my gf as she was sitting on me. I thought, this is enough and said ‘You’re my big sister!’ She let me up. But I was never more embarrassed in my life. We didn’t date much longer after that, and I bet she tells her friends about it as a hilarious story. My sister told this story once in front of my family and it brought back all those embarrassing feelings” (Source).
Ego Completely Destroyed.
“I met a really nice girl through some friends at work and asked her to go to the beach one afternoon. I picked her up for our first date in my little two seat sports car and we set off for the beach. As we approached the coast it became obvious that it was foggy and not going to be a nice beach day. We decided to try heading a bit south to see if the weather might be a bit better. I took a small twisty road I had not been on in a long time.
I guess I was showing off a bit in my little sporty car and came around a corner to find the pavement ended and the surface turned to gravel. The car spun and rolled up on its side, my date on the high side. The car hung there for what seemed an eternity, then fortunately fell back on its wheels with a crunch.
An inspection of the car revealed that besides some scratches on the driver’s side paint the only significant damage was the ripping off of the exhaust system and my totally destroyed ego.
After calming down a bit and some discussion, to my amazement she agreed to forget the beach and come with me to a restaurant for dinner. I loaded the remains of the exhaust into the little back storage compartment and off we roared, no muffler, open exhaust pipe, to a rather nice seafood dinner.
By the way, we celebrated our fortieth wedding anniversary this year” (Source).
Making A Bad First Impression.
“I went to a club with friends and saw a girl. She was being ogled by (me and) all of my friends, and eventually I came to realize that I had seen her before. I told my friends that I knew her, and they didn’t believe me and challenged me to go talk to her. She was just about out the door when I caught up to her. When I started heading over to approach her, I was sure I would remember where I knew her from by the time I got there, but as fate would have it, I did not. So, when I caught her, I said, ‘Excuse me, but I think I know you from somewhere.’ She replied with the obvious, ‘Where?’ and I stammered something about one particular dive bar. She said with disdain, ‘I have only been there once, that place is a dump!’ and she began to walk away. I grabbed her arm and said, ‘No really, I think I know you from somewhere…’ to which she replied, quite irritated at this point, ‘Where?!?!’ As this is all going down, I am racking my brain trying to figure out that exact answer. Tickling my memories is a vague recollection that she may have danced with one of my friends, so I proceeded to tell her that and that his name was George. She replies with, ‘George? Wait, George in the Air Force? Oh I remember you! You’re the guy who kept staring at me all night!’ It was true. Yet this started a conversation which led to dancing, having a really good time, and giving her a ride home (where I got a passionate good-night kiss and her number). Nice story, but not the really embarrassing moment…
All the following week, I try to reach her to go out with me, but to no avail. On Thursday, my friends invite me to go to a rocker bar with live bands the next night. There was about 8 or 9 of us going. Early Friday afternoon, my phone rings and it’s the beauty. I ask her out for Saturday, and found out she already had plans, but she was available this night. Not being one to flake on my friends, I tell her where we are going and that she is welcome to come with us. She said it sounded fun. When I arrive at her apartment she is wearing a skin-tight, black, leather, mini-dress. My jaw dragging on the ground and I am as flustered as I could be on the way to the bar. We walk in and here is the scene: Live band playing VERY LOUD THRASH ROCK MUSIC, my 8 other Air Force friends (all male), me, and the hottest girl most of us had ever seen in person! I offer to buy a round of MGD and as I was sitting back down, someone tapped the top of my beer bottle with the bottom of theirs, which caused my beer to foam. I had to chug some or have it spill all over. I chugged and returned the favor to them. My date says to me, ‘How do you do that?’ so I told her to hold on tight to her beer and I tried to tap the top of her bottle. This is when it gets weird! MGD bottles had rings in the glass on the bottom, and somehow I managed to align the bottles perfectly so that the ring on the bottom of my bottle sealed on the top of hers. The resulting air pressure produced inside her full beer bottle caused the entire bottom half of her bottle to literally pop off and the entire beer poured all over her and her leather mini-dress! After about 2 seconds of shocked silence, my ‘friends’ began to bust a gut laughing. My date was completely drenched in beer and there was nothing I could to even help wipe her off without appearing inappropriate, so I just started grabbing napkins and handing them to her. One of my friends said, ‘Nice first date Ron!’ and I replied, ‘Well, I will tell you this, if she goes out with me again, I am going to marry her!’
In July, we will celebrate our 18th wedding anniversary” (Source).
Came Back To Haunt Her.
“There was a guy at my school that I thought was super cool. Somehow in conversation, sushi came up and he said he loved sushi, so I said ‘Oh my gosh, ME TOO! Love the stuff! Yum-o!’ But here’s the thing… I was a total liar. I had never tried sushi. I couldn’t even use chopsticks properly.
A year later, this guy ended up asking me out. He picked me up for our date, and as we pulled into the restaurant I realized that he had taken me to sushi. I had forgotten about my big lie a year earlier. S–t.
We sat down to eat and I was desperately taking my cues from him. As soon as I attempted to grab the first piece of sushi, my chopsticks twisted up and I flung it across the room. I was horrified and quickly ran to pick it up and put it on my napkin, while he gave me a funny look. I took a deep breath and gave the second piece a try. I managed to get it up to my mouth for a bite (which I HATED), and it just fell apart- rice, soy sauce, fish…everywhere.
As I sat there frantically stabbing at the pieces of rice and fish that are on the table, he asked me, ‘Kate. Have you ever had sushi before?!’ I couldn’t lie anymore. I cracked. No, I hadn’t had sushi before. I was just trying to impress him. Luckily, he thought this was absolutely hilarious and ordered us some teriyaki chicken- and FORKS- and we had a wonderful rest of the date” (Source).
Stomach Hurts Just Thinking About It.
“My very first dinner and a movie date happened in 11th grade. It was a double date, my best friend and I and two guys who were friends with each other. I think we all wanted moral support and it was easier this way.
Everyone was nervous as hell, nobody knew if we were supposed to pretend to be grownups or just have fun. We all chose wrong. We tried to be ‘adult.’
Before ordering, my friend and I conferred in the Ladies’ Room about what to get. We didn’t want to be expensive or inappropriate or look piggy. She said we should both ask for French Onion Soup. She had all sorts of reasons, though I don’t remember what they were. I trusted her. We did that.
Think about it. A bowl full of melted cheese and onions. Tasty and inexpensive, sure. But it’s also gooey, impossible to eat delicately, and let’s not forget the intestinal and olfactory after-effects. I spent the entire rest of the evening trying neither to fart nor to breathe on my date. My stomach is cramping now just from the memory” (Source).
Young And Stupid.
“I picked up a cute guy in a campus bar, and for once my wingman-girlfriend got the ‘friend.’ She was not happy playing second string. Anyway, we went back to their apartment and had great water-bed sex all night. The next morning I discovered that I was sleeping on a wet spot and assumed that it was spunk. I staggered to the bathroom to pee and discovered that my period had started, big time. It was almost like a faucet was turned on as I sat on the stool.
I made up a makeshift pad with toilet paper and Kleenex and waddled to the bedroom to retrieve my scattered clothing. That’s when I got a good look at the waterbed. It looked like someone had been murdered. I flipped the top sheet over the stain, grabbed my clothes and struggled into them in the bathroom. I tiptoed into the other bedroom and shook my girlfriend awake, motioning that we had to leave NOW.
We sneaked out without wakening either guy, leaving skidmarks tearing away down the street. It was not my finest moment. I always wondered if he had the sense to soak the sheets in cold water. I know—I should have fessed up and helped him clean—but I was 21, stupid and still stoned from the night before” (Source).