There are some dates that are so disastrous, they’re unforgettable. When it comes to the dating game, these Redditors struck out big time—but at least they were left with great stories to tell.
1. A Crash Course In Romance
We decided to meet face-to-face at a common diner after connecting online. I was the early bird—but, everything turned upside down the moment she made her entrance. She confused the gas pedal for the brake, crashed into the sidewalk, and then into a street lamp. The lamp didn't stand a chance and toppled onto a van parked nearby.
By some miracle, nobody was injured but she was visibly mortified. I haven't heard from her since then.
2. Fine Dining
So I swiped right on a guy on Tinder who proposed going out for dinner. I thought, "Why not?" so later that evening, he came to pick me up. As we hit the road, he wondered where I'd like to eat. My response was casual—"Anywhere's fine by me". Little did I know, I had set the stage for disaster.
Seizing on that, he grinned, saying, "Alright then," promptly steering into a Subway parking lot. Surprisingly, he confessed he wasn't hungry but urged me to grab a bite. So, awkwardly, I got myself some food as he stood there, observing. Internally I was reeling, but a morbid curiosity made me wonder, "Could this go even further south?" Spoiler: it did.
Next thing I know, I'm back in the car, clasping an undesired Subway sandwich, while this brainiac decides to take a joy ride, aiming for a secluded, shadowy ravine nearby. We drive into the heart of the ravine—about 10 minutes deep—before he parks by a forsaken tennis court and says, "Okay, you can eat now."
Anxiety surging, I'm thinking, "I sure hope this isn't my last supper," as I struggle to swallow the damp sandwich under his gaze. The minute I finish, we're on the move again, heading back home. Relief washed over me as I finally got home safely, but it took several days to fully comprehend just how nightmarish the whole encounter had been.
But wait, there's more! The icing on the cake was his unannounced return at 2 am that night, bearing a bag of stale donuts, and casually asking me if I fancied sleeping with him.
3. No Means No
Once a dinner and a movie date concluded, he queried if I wanted to "enjoy some amusement" and swiftly removed his trousers. My response was a firm "No". He expressed apologies for crossing boundaries, to which I replied, "Hey, it's fine and I totally get it!"
Here comes the part that puzzled me...he interpreted my "fine" as an agreement to his earlier proposition. Without a second thought, he quickly undressed again. It became quite uncomfortable when I had to clarify my stance was still a no.
4. Just Can’t Catch A Break
During my college years, I once asked a girl to join me for dinner and she agreed. I was overjoyed, but also faced the challenge of choosing a venue that would reflect my identity and values. I needed to be considerate in my choice.
There are two types of presents: luxurious and thoughtful. Since I wasn't able to afford luxury, I decided to put considerable energy into being thoughtful. Her being a freshman from Pennsylvania and us being in the southern US, I thought of something that would seem novel and fascinating to her. That's when it struck me: Bojangles!
Bojangles was economical, it used to offer fairly good meals, and it was distinctly southern. It would give us the opportunity to chat about regional culinary and cultural distinctions. The flipside, however, was that it served fast food of rather low quality.
The date night arrived. I drove her to the restaurant while discussing the southern way of life, comparing it to the North, and chatting about fried chicken and tea. We arrived, placed our orders, and started waiting for our food. We kept waiting and attempted some light conversation.
Finally, my fried chicken and drinks were ready, but her sandwich was missing. We stood there in growing awkwardness until one employee finally asked if we needed anything. I told him we were waiting for her sandwich which, to our surprise, had been ready all this time. Not exactly smooth sailing so far—and it got worse.
Nonetheless, I picked up the tray and headed towards a table. I faced a small hiccup. Bojangles was famous for its sweet tea, and I'd ordered a large one. These cups were designed to fit car cup holders, which made them staggeringly imbalanced on the tray.
The cup tipped over, knocking her drink—which was in a wax-paper cup—off the tray and onto the floor. When the cup hit the ground, it exploded, splashing soda all over her shoes.
Gallantly, I fetched her a fresh drink. On reaching the table, I realised I'd ordered a food item (fried chicken) that required finger eating. Not exactly the wisest choice for a first date. Hoping to avoid appearing foolish, I decided to use the spork Bojangles provided.
It was no good, as the inadequate plastic cutlery couldn't prise the chicken off the bone. In the struggle, the chicken shot across the table. Luckily, I caught it in mid-air.
Resigned to the unfortunate turn of events, I decided to dig in using my hands. Anticipating no future dates, I decided to stop trying to impress her and simply salvage the situation with dignity. But it was not to be. Somehow, I ended up smearing chicken grease all over my face instead of getting the piece into my mouth.
Her expectant look suggested she was hoping for a revelation that this was some prank. We finished the meal in silence. Deciding to end the disastrous date, I cleared the table and managed to throw not only the trash, but also the tray into the garbage bin.
We exchanged knowing glances and dashed to the car. I've had my share of disastrous dates, but this one truly stood out. I was even surprised that my car started without a problem, given the luck I'd had that evening. Safe to say, this was an unforgettable experience.
5. A Brutally Honest Red Flag
From my experiences working in bars and restaurants, I've seen some incredibly memorable moments. This incident really stands out, and let me tell you why.
On a relatively calm night, we had an early dinner booking for two at 6 pm. A young lad arrived about 10 minutes prior to the reservation time. He was visibly anxious, admitting it was a first date for him – a situation he hadn't often faced. It was quite endearing, truth be told.
After we settled him in, his date arrived half an hour late. She, however, proceeded to drink way too much. The situation took a sharp turn when she answered her phone in the middle of their meal, openly discussing her date with the person on the other end. Her words made it clear that she wasn't particularly taken with him—she conceded she had agreed to the date since she had nothing else going on.
Seeing his discomfort and disappointment, the young man paid his bill and left. Fortunately, the experience didn't seem to dampen his spirits. He's a good chap, and I've spotted him a few times at the bar I currently work at.
My most cringe-worthy date was actually my introductory online date. We had started chatting on a dating platform and decided to meet face-to-face at a nearby cafe. I decided to head there 15 minutes in advance. Upon arriving, I received a call from her informing me she would be slightly delayed.
I signed off saying it was not an issue. Not long after, another call came through—she was late again because she'd managed to lock herself out of her flat.
I continued waiting. An hour after our planned meeting time, a woman who resembled the picture on her profile walks into the cafe. As I was about to walk over to greet her, my phone buzzed.
I answered it, only to hear her yelling, "Where on earth are you? Are you playing games with me?" I assured her I was sat discreetly at a table in the rear of the cafe.
This initial online date was undeniably eye-opening, as I realized why some women choose to only post headshots. She was considerably overweight. Moreover, she came dressed in casual sweats. But all of these paled in comparison to what followed next.
After making a bit of idle chit-chat, I innocently asked her how her day had been. She counter-asked if I genuinely wanted to know. Regrettably, I said yes.
She instantly dove into a tirade detailing how she had lost her previous job because her colleagues had conspired against her. She had got a new job which turned out to be a sham that robbed her of her credit card details.
She then mentioned she had recently ended an abusive relationship, and her sister, who was 25 years old, was leaving their family to relocate to the Big Apple. As if that wasn't enough, she had been expelled from her school on unfounded allegations of planning to harm someone. According to her, she found herself frequently on the receiving end of unfair accusations.
I was shell-shocked and couldn't get myself to exit immediately. So, I remained seated for another seemingly long hour, making desperate attempts at continuing our excruciatingly awkward conversation.
7. Are You Afraid Of The Dark?
Before getting engaged, I enjoyed the casual dating scene. There was this one guy from high school I started talking to. He was attractive and I thought trying a date could be interesting. I proposed he came over to my place for a laid-back Netflix evening rather than going out on a formal date.
He shows up and all seems fine until we sit down in my living room to start watching Netflix. Both of us settle on the couch, with a single corner lamp illuminating the room. Out of the blue, he suggested we should turn off the lights. Not a big fan of complete darkness, I countered that the corner lamp provided enough light.
Suddenly, he stood up, quietly walked over to the corner, and began to rhythmically turn the light on and off. The corner where he stood was right next to the kitchen entrance, and he was silently flicking the light, not uttering a single word.
I had to say out loud, "This is getting creepy, haha, please take a seat". His reply, interspersed between the light flickers, was "Why...are...you... scared... of... the... dark". He then purposefully half-hid himself behind the kitchen doorway, keeping a hold on the light switch.
He then started giggling eerily like a child while continuing to play with the light. Needless to say, we didn't go on any more dates after that strange encounter.
8. Dine And Dash
Both of us were pretty tight on money, so we opted for a simple walk in a charming, small town nearby. We then decided to grab McDonald's and eat in the car, extending our conversation a bit further. Not too long after, he started trying to convince me that I should sleep with him, claiming that I owed him for the cheeseburger he bought.
Things got even scarier after that. As he became more insistent, I suggested we drop by the gas station across town to get some protection, a detour I had a plan for. Since I was the one who drove, I handled the journey to the station and asked him to fetch what we needed while I stayed at the wheel.
Once he entered the station and moved a bit deeper inside, I took that as my cue to exit, stranding him there. This was back when cell phones weren't a common thing, and the town had no bus service, rideshares, with most facilities closing by 6 pm.
Through friends we have in common, I learned he somehow managed to get home. But they were already aware of the real reason he was abandoned at the gas station, so nobody really took his complaints seriously.
9. Doggone It
I ran into a chap at a business networking event. He was an intriguing character. After chatting for a while, he invited me over for Chinese take-out and a movie at his place, pre-conditioning that I meet his four furry friends first. Quite reasonable, I thought, as I'm an absolute dog lover.
I navigated to the location he provided, only to discover it was a trailer with a petite, fenced-in yard. Naturally, I assumed his dogs would be of a smaller breed. Much to my surprise, I was greeted by four gigantic dogs with zero etiquette; they seemed crammed within the interiors of the trailer, which was heavily permeated with their scent.
To my shock, "dinner and a movie" translated into sifting through his extensive collection of VHS tapes and DVDs whilst fending off his advances, all amidst the chaotic antiques of his over-sized canine companions. Graciously, I declined his rather bold invitation to amplify the evening by exploring the bedroom, and I swiftly made my exit.
My attire went straight into the laundry as soon as I reached home and unfortunately, my car retained the strong dog odor for several days afterward.
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10. Didn’t See That One Coming
When I was about 19, I was hanging out at a bus stop, killing time before heading to work. A really striking lady took a seat next to me. It wasn't long before we started to chat. Our conversation flowed naturally, and eventually, I found the guts to ask her if she'd fancy catching up at a local coffee joint.
To my surprise, she agreed! We decided on when and where to meet. As I was getting on my bus, she lastly quipped, "It's a date". I showed up at our chosen coffee shop at the agreed time, only to find she had arrived before me. But that wasn't it—she was also accompanied by a guy.
I didn't make much of it, thinking he might be a safety net in case I turned out to be a weirdo. So, I took a seat opposite her and we got ourselves a drink. The very next moment, she goes, "So, what's your take on Jesus?” and opened a leaflet she had brought.
With surprise, I responded, "I thought we were on a date," only for her to counter with something like "I wasn't sure you'd turn up if it wasn't”.
The encounter left me so upset that I hustled out of there before she could see me getting teary-eyed. In hindsight, that experience counts as the worst date I've ever been on. Oh, the humanity!
11. The Secret Ingredient
I once went out with a woman on a blind date who kept peeling off her scabs. She had collected them into a heap right there on our restaurant table. I excused myself for a brief trip to the restroom. On returning, I noticed my soup had arrived, but the pile of scabs was mysteriously gone. Rest assured, I decided not to touch the soup.
12. What’s My Name?
I once went on a date with a coworker I didn't know very well. Unfortunately, it was a disaster—he showed up drunk and was behaving terribly with everyone around us. The worst part of the evening was when he openly taunted a small band that was performing at the bar.
The lead singer, frustrated, offered him $10 to guess my name. As you may have predicted, he couldn't remember my name despite us spending the evening together, and this happened in a room full of people. The surprising part is what happened after—the very next day, he texted me suggesting, "You can try again," as if I was the one who messed up the evening.
13. The Babysitter
I had been chatting with this gentleman, and we eventually agreed to have a date. He promised a dinner and drink outing, and even offered to pick me up after my job, which I accepted. He texted me: "WE'RE on our way"; I swiftly queried, "Who's we?”
Turns out, he's a solo father. He had arranged for his sister to care for his four-year-old son, but last-minute changes happened. Even though I was surprised, I went with the flow. He noted he needed to head home first for a shower, since he was still in his work attire.
Upon arriving at his place, he went for a shower and ended up snoozing for around four hours. During that time, I spent time with his child, who surprisingly hit me in the face TWICE! Thankfully, after asking him not to repeat it, we warmed up to each other and enjoyed our time together.
The little one turned out to be delightful. Eventually, the man woke up from his nap, and we settled for a pizza meal. I chose to Uber back home. I would have left earlier if he was awake, but I didn't want to abandon his child alone.
14. Get My Good Side
I got to know a guy on the internet. Living in a medium-sized city myself, and him being in a tiny, quaint town about 40 minutes drive away. He suggested I make the trip to visit his place. Truth be told, I was hesitant. With the lack of activities in his town and the ultra-traditional nature of its inhabitants (considering we're both guys) it wasn't my first choice. But, heck, I decided to go for it.
Our date mostly consisted of him passionately delving into some pretty wacky conspiracy theories he held. For instance, he asserted prominent politicians and starlets are devil-worshipping Illuminati under the Catholic church's control. You name it. But, the most bizarre element of the date? This guy had a habit of positioning himself at a 45° angle from me during the entire date.
For example, he sat askew in his chair whilst dining, and if he was upright, he maintained a side-long posture. In a quirky move, I shifted to enter his line of sight for some eye-to-eye contact. And, what do you know? He just spun another 45°!
15. Let’s Never Speak Of This Again
I still get embarrassed remembering this date, which was about 12 years ago. We'd decided to have some food and drinks and everything was going perfectly— we clicked well. As we began our walk back to the train station, I felt a sharp pain in my stomach. I must have eaten something bad.
I tried to keep calm and told myself that I'd use the restroom at the station. But when we reached the station, the restrooms were closed for repairs. The pain and cramps were getting worse, and I was starting to sweat. I tried to sustain the conversation with my date, but all my thoughts were on avoiding an embarrassing accident.
When the train pulled in, we boarded. I couldn't face using the cramped and potentially busy train restroom given the situation, so I decided to cut the date short and told my date I needed to get home. My stop came soon enough, so I muttered a quick goodbye and disembarked.
By this point, the cramping, sweating, and sheer discomfort had intensified. So as soon as I stepped off the train, I began to jog towards the station exit. However, I tripped over my own feet and landed flat on the cold station platform. The severe impact caused me to lose control of my bowels.
Making the situation worse was my date, watching in disbelief from the train window as it pulled away. We never touched base afterwards, not needing to; we both knew the full story of that disastrous station incident.
16. It All Came Crashing Down
This is a story about a close pal of mine. Her date took her to his usual rock-climbing gym in town. She mentioned that she had some climbing experience and appeared to be in good physical shape.
However, within 30 minutes of their arrival, the worst happened—she had a fall and ended up with a broken arm.
17. Licky Licky
I had an encounter with a guy that I first met at a coffee shop. He seemed nice at first, and we caught up over coffee again before deciding to go out for dinner at a bar. While we were at the bar, a very odd incident happened.
As I turned to try to get the bartender's attention, this guy suddenly— believe it or not—licked my face from chin to temple. I was taken aback, to say the least.
He then made an attempt to lighten the mood by playfully poking me, but when I asked him to stop, his response was completely out of line. He leaned in close and whispered, "I'll just poke you while you're asleep instead"...
I asked him to leave at once. I accompanied him to his car with the support of a bouncer who stood guard by the door to ensure my safety.
A few days later, I received numerous messages from him. He seemed worried because he hadn't heard from me and mentioned plans of "visiting my parents to check if I was okay". The troubling part was, I had never discussed my parents or their address with him. I decided to warn him that I'd contact law enforcement if I ever heard or saw him again.
Thankfully, since then, I've not received any further communication from him.
18. Signs From Above
We took a leisure stroll, and in a playful spirit, we started rolling down a grassy hill. Unintentionally, we found ourselves behind a Mormon Church and got a little carried away. However, our fun was interrupted by a observant Mormon, who chided us for our inappropriate behavior, and he watched us put on our clothes in an awkward silence.
So, we moved to a different location, but both of us were complaining about the abrupt interruption earlier. The next spot, however, was worse—around 30 mosquitos decided to make a feast out of my backside, with two bonus bites on my private parts.
It was quite the dinner party! She wasn't spared the misery either, as it turned out she rolled over onto dog poop, causing her to weep at the unfortunate wardrobe incident.
It felt as if God was murmuring from above, "You guys ought to rent a room."
19. Money Matters
He took me to an eatery that served Italian cuisine. Soon after we made our orders, he received a phone call. He engaged in casual banter with the caller, then I heard him say, “Mom, I understand, I picked the least expensive item on the menu. Mom! I'm in the company of my girlfriend. I'll let you know about the total bill later."
This rubbed me off the wrong way for two reasons. First, it was our initial outing, and I certainly wasn't his girlfriend. Second, he shared a house with his mom (which...okay, I could somewhat stomach), but it shocked me that she was so controlling of his finances—so much so that she decided to ring him during our meal to monitor his spending. It felt incredibly unnerving and bizarre.
I decided to meet him once more to ascertain if he was as peculiar as I thought, and it turns out he was. So I ended it there.
20. Running Him Ragged
Well, I botched that first date. I seriously miscalculated the time he (because I'm a woman) would need to cover a seven-mile hike. I had no other choice but to phone a friend to contact the park rangers because we were still on the trail past 9 pm—way after the park gates closed.
During the home stretch—those grueling final three miles—he really gave me the ick. resorted to encouraging his own legs and joking about munching on the hopping frogs crossing our path. It was pitch dark, and he'd left his phone, so I lit the way with mine. My apologies to you, dude. You're a really great guy and I honestly didn't mean to physically wear you out on our walk.
21. Drink Up
I connected with a girl online and we struck up a conversation. Things were going great between us as we were constantly texting and seemed to have a good connection. Eventually, we decided to meet for dinner and although everything seemed fine, she did appear a bit unusual.
During dinner, we ordered a batch of margaritas. After just our first round, she suddenly stopped speaking mid-conversation and was simply gazing at her hands. I asked her if she was alright and her response was, “Oh, I'm sorry, I'm a bit tipsy”. I was surprised and thought, “Really? We've only just started drinking”.
Then she confessed, “Oh, I've been drinking all day”. This had me reflecting over our prior text exchanges where she frequently messaged me saying, "Hey, I'm a bit tipsy on my way home, keep me company". Alarm bells started to ring, making me think this might be a habitual thing for her.
The next thing I knew, she passed out and hit her face on the table. Initially, I thought she was joking because of her dramatic reaction.
I started worrying when she didn't move even after I laughed. I had to wake her and quickly called for the bill, which turned out to be more expensive than I'd anticipated.
She then requested if I could walk her home, and despite her being in a bad state, I agreed. As we kept walking, I got curious and asked her how much further her place was and she said it was another mile away.
After a while, we finally reached her apartment. She offered me a drink and then asked if I wanted to stay over, to which I politely refused. Upon my refusal, she got upset and promptly kicked me out. And that was it! I had to use a GPS to navigate my way back to my car.
22. Drama King
Well, technically speaking, this is about calling it quits, but it unfolded during a date. I attempted to end things privately while we were in the car. He asked for a brief hiatus in our chat, then led us into an eatery, and shockingly, started sobbing in public view.
The most interesting part? A few weeks afterward, he showed up at my workplace, acting as if we didn't split up. So, I had to dump him...again...while he burst into tears... and his sister, who is also my colleague, was present too.
23. Telling Tall Tales
Once, I had to be the rescuer during a friend's date. Just as she suddenly excused herself for a bathroom break in the middle of the date, I knew I was about to receive "the call". She returned and continued chatting for a while, and her excuse was pretty fascinating, to be honest.
She didn't give me the typical "my friend is in trouble" spiel. Instead, she spun a tale about a bus accident and claimed she needed to rush back to the hospital to attend to several tragically deceased children. Quite the intriguing story, I must say.
24. Good Enough
My first date, which also happened to be the worst one I've had, started with a painfully lengthy car ride. All the while, he incessantly talked about his passion for nightclub life and the perks of bottle service. We finally arrived at what he deemed a "suitably low-key restaurant for a girl like you."
The moment we had ordered, he nervously proceeded to check his bank balance. This led him to bluntly instruct me to cover dinner—which I would've been okay with if he asked in a slightly more considerate way.
For the rest of the meal, it seemed like he was the only person entitled to talk. He embarked on a rather bizarre monologue about his firm belief in a flat Earth and his ambitious plan to become a senator of Mars in a decade...and it gets worse.
He emphasized that any woman serious about dating him would need to be very supportive of his dreams. Once dinner was done, I found myself reluctantly following him into a club—he was my ride, after all.
When he cheerfully declared, "This is going so well", I had to disagree, stating that it wasn't quite the case given I hadn't had much of an opportunity to share my thoughts. When he asked me to list examples, I plainly told him it was the worst date I'd ever been on. Unfazed, he sat down next to me and optimistically asked, "So we can maybe transition from friends to something more?"
My immediate response was to call an Uber. The texts for another date flooded in every day for a week until, finally, I just blocked his number.
25. Shortchanged By The Universe
I got to the coffee shop super early because I was pretty jittery. As I parked, I discovered that I'd left my wallet back at my place. Just my luck, the coffee shop was a half-hour drive away, and our meet-up was due in 10 minutes.
Fumbling around in my car for spare change, I managed to find $2 in quarters, nickels, and dimes. I scampered into the shop and picked up the most inexpensive coffee they served. She walks in, clearly surprised I already ordered something. I mean, how chivalrous of me not to offer to buy her coffee with the rest of my change, right?
We chose a spot outside where the lowering sunset hit right in my eyes. I was too stubborn to relocate, so I spent an entire hour squinting, bathed in bright sunlight. The chat was actually enjoyable, but it all went downhill when I shifted in my wooden chair and heard an alarming CRACK.
Just my luck, the chair was indeed broken. I mean, I know I'm a big guy, but did this really need to happen at that exact moment? So, I was hardly shocked when she didn't return my calls after our first date.
26. Well, That One Backfired
I haven't experienced many romantic outings, but the most disastrous—and amusing one—happened through Tinder. The idea was to kick off the evening as a double date at my place, and then, if things went well, we would part ways and do our own thing.
However, we never reached that phase because he ended up clogging my toilet with too much toilet paper after using it. He was mortified when my friend discovered the situation and decided to make a quick exit. To top it all off, he left his coat behind in the hurry, so one of his pals had to swing by the following day to retrieve it.
27. Dr. Yuck
In conversation, he told me, "I'm not one to boast about my work, but just so you know, I save lives every day." What he meant was, he's a doctor. He voiced that without the slightest hint of sarcasm. But then, he started to get upset. It turns out, he had messaged me on a dating app half a decade prior to our date, and was quite peeved because I didn't reply instantly.
When I clarified that the account was old and one that I hadn't used in quite a while, he smirked, "Just goes to show how fickle girls can be…” And guess what his big reveal was? Turns out, he was actually suffering from strep throat and confessed, "I actually shouldn't be on a date right now." How disgusting!
28. Third Time’s The Charm
When I was in tenth grade, I had made plans to watch a movie with my date. At our first theater choice, we were asked to show IDs which was a novel experience for me.
I immediately froze. Unfortunately, as I was under 18, I wasn't able to buy the tickets. At theater number two, due to malfunctioning air conditioning that caused the temperature to soar up to 95 degrees, the movie was called off.
At the third theater, we faced a new predicament—there were no two seats available together. Despite that, my date still wanted to see the movie so we ended up sitting IN SEPARATE ROWS. As you might guess, there was no follow-up date.
29. A String Of Bad Luck
Honestly, choosing my worst date isn't an easy task. I've had my fair share of disaster-date moments. One time, I had a partner who came off as normal until she led the conversation towards believing we're all part of some grand simulation, like the Matrix.
I also dated someone with a biting issue. Having to show up at work and family gatherings with a bruised, battered neck wasn't exactly fun, and it left me fearing for my life. Once, a date ditched me at a club, leaving me bustling amidst a crowd, way beyond my introverted comfort zone.
To add more flavor to this date cocktail, I can recall one night when, after a long walk home alone, I ended up having an embarrassing pants-incident because I was overly intoxicated and didn't really mind it amidst a downhearted phase. So, you see, navigating through my dating world has always been a bumpy ride.
30. Is That My Ride?
So, a buddy of a few pals once invited me out. He snagged my digits and rang me up for a dinner date. Curiously, he asked me if I'd be cool with him showing up in the vehicle he used for work.
Now, I've been in the business environment for some time, so I figured it's probably some sort of company car. No big deal, right? Looking back, I probably should have inquired about his job.
Fast forward to the evening of the date, and he pulls up... in a trash collection truck. But it gets even better. I tell myself "Why not, I did agree to this after all," and we head off for our meal.
Now, my guess is that poor guy was a bundle of nerves because he ended up getting way too tipsy. So tipsy, in fact, that he even asked me to drive his huge garbage truck back!
Here's the catch: this monstrous machine has four shift levers, and I only know how to drive automatic cars. And yet, this goofy guy ends up driving me back home – yes, in the trash truck. He even dared to ask if he could stay the night.
Needless to say, there wasn't a second date...
31. Playing With Fire
My initial dating experience takes the prize as the absolute worst. The gal I was with began striking matches, snuffing them out using her fingertips, and then chomping down on the charred end of the matchstick.
32. Just Watch Me
My most disastrous date happened back in boarding school on a university campus. We were both rule-abiding nerds, and so we decided to attend a party at the student center. However, he got fed up after about a quarter of an hour, and we slipped away into the campus buildings. I assumed we were sneaking off for a little romance? Nope.
Instead, he ruined his chances with me completely. We stumbled upon a computer lab and he proceeded to spend the next two hours showing me how he played League of Legends while attempting to give me a rundown of the whole game. So, if you come across an attractive, single guy, there might be an underlying reason.
33. It Was Like Watching A Car Crash
Her profile pic online was attractive, and we had around four or five pretty standard chats before we decided on a movie for our date. I'm not usually a fan of movie dates since they limit real-life conversation and getting to know about each other, but I thought, “She seems nice, what could possibly go wrong?”
Be aware that she was the one who picked the movie time and when I would be picking her up, so it's not as if she was clueless about bathroom availability. The cinema was just about 15 minutes from her place.
The moment she hopped into my car, it was visible that she was under the influence. She even warned me with a mock kick-fight if I tried anything silly. All of this barely took 10 minutes.
Exactly at the 10-minute mark, she asked me to stop the car, and what she did next was mind-blowing. She stepped out of my car right there on a rather busy highway, and, within my view, she began to relieve herself…
It was one of those moments that you find hard to ignore. Once my brain figured out what she was doing, I quickly leaned over, shut the passenger door, and left.
34. The Double Date Disaster
So let me paint you a picture of my very first date. I was just turned 16, and the guy from school was decently cute. My expectations weren't high, but somehow, he slipped beneath them.
Trusting people isn't my thing, hence I insisted we go out with another couple. Now, he had many friends who I was familiar with, so he guaranteed me it would work out. But the surprise came when I dropped by his house, the "other couple" was his aunt, with whom he shared his home.
Now imagine this, a 21-year-old aunt, a clueless 16-year-old me, and a guy who had no clue he was scheduled for a date, he thought we were just hanging out.
To elevate the weirdness, the aunt decided to cook Hawaiian haystacks for her Polynesian date who had no idea what they were! He walked into badly burnt rice; he rescued it while the rest of the food came straight out of cans.
As if they hadn't messed up enough, they decided throwing blades in the backyard was a good idea. When I outperformed my date and his aunt hit him with an airsoft BB, he was really upset.
To lighten the atmosphere, his aunt suggested we go bowling. All I had were ballet flats, which meant borrowing his extra-large 2010-style nerdy socks that had mystery stories I'd rather not know.
Before leaving for bowling, he tried to bolster his dented ego by kicking a spider on the wall, only to end up kicking a hole in the wall and getting his leg stuck. His aunt had to come to his rescue. Impressed, I definitely wasn't.
Eventually, we arrived at the bowling alley. It started off well, but tension rose when we found out the manager was the aunt's recent ex. To top it all off, he tried to kiss me in the back seat of the car under the watchful eyes of the aunt and her date. She even gave a cheer.
You might think that was the end of him and me, but as it turns out, this wasn't even the worst date I endured in high school.
35. Taste Test
He dipped his fingers into my dessert, tasted it, and repeated the action! I had ordered lemon meringue pie and kindly asked if he wanted to taste some. He initially refused, but later changed his mind saying, "Actually, it does look yummy." And then he went for a finger lick. So unappetizing!
36. A Night To Remember
A few years ago, I took an extended vacation during a particularly challenging period in my life. I went to Colombia to study Spanish. While out one night with some buddies from my language school, my eyes landed on an undoubtedly gorgeous woman. Even though my Spanish was still rudimentary, I felt a strong urge to ask her out.
So, that's exactly what I did—I mustered up the courage and asked her out. Shockingly, she agreed. Fast forward to the following day, the day of our date. I was feeling a bit under the weather, but the excitement overpowered any illness. True to our plan, I picked her up and we headed to a lovely restaurant. After our meal, we strolled along the beach—a bit cliché, but indeed true.
It was at this moment that my ill feelings escalated. Dizziness consumed me and the inevitable happened. I got sick—not just a little, but dramatically, expelling everything my body could muster. My memory from that point is hazy, but I eventually woke up in a hospital.
Beyond my surprise, my date was there next to me, now dressed in workout clothes because my accident had, unfortunately, caused a mess. She expressed genuine concern and remarked that we hadn't gotten to complete our date. Now, years later, we're preparing to tie the knot,
37. He Got Gassed
So, the absolute craziest date I ever had started off like a typical high school situation. This girl set up a date at her house, taking advantage of her parents being out of town on a weekend trip. I was game for it and everything was shaping up nicely.
As the night wore on, we found ourselves sharing the bed. Suddenly, she just conked out. Snoring and fast asleep, while I stayed wide-awake at 3 am. Then, she stirs a bit and suddenly lets out a fart I swear could have woken the dead.
It was one prolonged session of flatulence… that just wouldn't stop. Initially, I mistook it for her ancient pooch. But then, nope. When the smell hit me, I nearly choked. With my shirt serving as a makeshift mask, I could only wonder what she had for dinner.
The cherry on top? The satisfied little noise she made when it was over. It was just too much. I couldn't stick around. I quietly got dressed, hoping not to disturb her, and crept down the stairs and out the front door towards home. My luck? She lived nearby, so it wasn't a long walk, at least.
Naturally, she caught up with me the following day, curious about my sudden disappearance. But I just couldn't bring myself to spill the beans. I felt it would be just too mortifying for her.
38. Three’s Company
I was planning on taking a girl to the cinema when she asked, "Could my best friend join us?" There went my romantic prospects, but trying to be obliging, I responded, "Absolutely!"
And so, she arrived with her friend who, surprisingly, turned out to be a guy. It's at this point when I discover that this 'best friend' is actually her ex, but they've somehow managed to maintain a tight-knit friendship and nothing more. I think to myself, "this date has gone off the rails, yet let's do what we can to make it enjoyable." I proceed to pay for our tickets, even though she kindly offered to cover her own.
After I've paid, she spins around and handles the ex's ticket. Oddly enough, we all got along and the atmosphere seemed pleasant, but it felt like a constant tug-of-war contest for the rest of the evening, as I tried to get her attention. It's no surprise that I lost, given that they're best friends.
Once I got home, her guy friend added me on Facebook and felt the need to say, "Don't even attempt to make her your girlfriend, she's no good at it." I finally got the chance to take her to the movies alone one more time, but our relationship sort of disintegrated. While I genuinely liked her, it was evident that I didn't make a significant impact on her. I guess that's life.
Word of advice for those planning future dates: steer clear of movie dates. They may not pan out as you'd expect.
39. Clownin’ Around
Certainly not my most horrible date, but it tops the list for strangest. I found myself out with a girl who was my type: attractive, funny, and enjoying similar hobbies. We were at a bar she frequented, getting to know each other, and the typical first-date questions began to crop up.
"So, you've mentioned you're in an office job, but is that your dream?" I ventured to ask, "Did you study for this field?" She responded, rather bizarrely, "Actually… I'm currently attending clown school,” and proceeded to pull out a bright red clown nose from her bag and put it on.
Had this been our third meetup, the surprise would have been slightly softer. But since this was our premiere outing just a week into knowing each other—when impressing is paramount—I was taken aback. But the fact remained—she was appealing, and I was intrigued.
So, I responded, "Wow! That's really interesting. I wasn't aware clown school existed!”
"Indeed, it's quite competitive!"
"I'm surprised. Do you attend a clown university, college, trade school?"
Apparently, she misunderstood my light-hearted jest as an offensive comment. Despite being a clown, her humor meter seemed faulty.
40. Equality At Any Cost
I went out once with a fella who wasn't really my type, looks-wise, but he seemed friendly enough. However, he spent our WHOLE outing boasting about his hefty income. We split a pizza—I had a single slice while he wolfed down half a dozen. His lack of chivalry didn't end there.
When it was time to settle the check, he suggested we split it down the middle "since that's how it's done these days". Afterward, he attempted to plant a kiss on me when he drove me home, and trust me, his breath... it was as if he'd dined on roadkill.
41. Got Milk?
Some years back, I found myself on a coffee date with a guy who was studying nursing. He shared an intense story about how he and his previous girlfriend had helped an elderly woman use the bathroom at a party. He mentioned it wasn't the first time he had done this, he just happened to have his girlfriend there to assist him.
The story was far from comfortable and I quickly made up a reason to take my leave. The funny bit came a few days later. He texted me asking for another date. I didn't respond. Then, the next day he sent another message: "It was because of the bathroom story, right?"
42. An Awkward Introduction
So there I was, all alone at the coffee shop. She dialled me up, explained she had a sudden crisis and couldn't show up. I'd only been waiting for about three or four minutes and I was cool with it. So I thought, "why not catch up with a buddy?" and gave him a call.
Long story short, he was on the other side of town, at a bar. So, I decided to join him. As it turns out, he'd just met this lovely lady over a game of pool and introduced me. That's how I ended up meeting my date for the night.
43. An Icy Encounter
During my university days, a girl I was fond of invited me to join her for ice skating along with some of her mates. I had no idea how to ice skate and struggled to grasp the skill swiftly.
However, I was keen on impressing her somehow. My ice skating efforts were unfortunately not successful and I ended up clinging to the barriers around the ice rink the entire time, making a complete spectacle of myself.
The apparent highlight of this ordeal was when I stumbled and fell flat in front of a group of people, just as someone clicked a photo. The timing of my fall resulted in my embarrassing moment being forever preserved in that picture.
Following the disastrous ice-skating experience, she escorted me back to my apartment and our blossoming relationship was abruptly halted. But, as the saying goes, every cloud has a silver lining.
Interestingly, my now-wife was also present at the ice rink that night. We didn't connect the dots until a couple of years into our relationship, when she unexpectedly exclaimed, "You were that guy who couldn't ice skate! Yeah, that girl didn't seem too interested in you."
44. Bragging Rights
During our second meeting, he took pride in sharing several things with me. First, how he had managed to receive unemployment benefits for a long period.
Second, how he could always convince his mom to let him back in the house, even after she had asked him to leave. Lastly, he mentioned that he had essentially financed a dancer's $3,000 implants, despite not receiving anything in return.
But the worst part came after—he admitted to having served approximately four months in jail for threatening some teenagers with a gun, but insisted he had no intention of using it. This was expressed more as a half-boast rather than a full-blown one. It was quite unexpected given his pleasant demeanor on our first date.
On this second outing, I found myself internally amused and contemplating how to conclude the date. Luckily, this wasn't an issue as he had plans to meet his friends at the video store after dinner.
45. Laying All Her Cards On The Table
The worst date I've ever been on? The girl I was with had Crohn's disease. In the middle of our dinner, she took out her urine bag and told me I should look at it to fully grasp what dating her could involve. Unfortunately, her catheter tube knocked over her beverage. It was a less than ideal situation. I really felt for her.
46. Momma’s Boy
On our first date, he decided to charm me with a dinner at his mom's place. Add to the mix, his brother and his mom's eccentric roommate. Post dinner, we all ended up watching Iron Chef, and due to a short supply of chairs, we gathered on the floor. Amidst the show, a rather unique conversation involving his mom discussing the utilization of vibrating appliances in house chores came up, suggesting it could make things more fun.
Here's the kicker: He didn't even reside at his mother's. Go without saying, that was the beginning and the abrupt end of our dating saga.
47. The Ole Switcheroo
My lousiest date began like a typical date, yet wrapped up as a multi-level marketing proposition. The silver lining? I still have those Cutco scissors, which aren't half bad.
48. The Stench Of Success
This story takes place on my third date with a woman. We decided to attend a Poison-Def Leppard concert. Since we hadn't planned on eating before the show, I picked up a chicken salad sandwich from a nearby gas station to fill my empty stomach.
In the middle of the concert, I was struck by an urgent need to use the restroom. However, the bathroom stalls were in a sorry state. Remembering our VIP status, I decided to postpone my visit and make a pit stop at the VIP bar on our way out.
Once inside, the powerful smell from my visit caused a commotion amongst a few guys nearby, which I couldn't help but find amusing. After the concert, we maneuvered our car out from the front parking spot to relax and take a breather. But then, the second wave hit me, and this time it was more liquid than the first.
I found myself gripping the steering wheel tightly and working up a sweat, much like being in a crowded all-you-can-eat buffet on a hot day. Suddently, I had a thought. A modest release of gas might alleviate some of the discomfort. Unfortunately, this idea backfired dramatically.
My pants turned into a disaster zone. I dashed into the nearby woods to finish up the unpleasant episode and used my undershirt as a makeshift toilet paper.
Despite this early misadventure, we've been happily married for 12 years and are the proud parents of three children.
49. Showing Off His Creepy Side
I once had a slight blackout at a nightclub where I quickly encountered a man in a suit whom I later learned was named Willis. The following morning, I found a message from him on my phone. Funny enough, neither of us had a vivid memory of the other. Willis seemed like a good guy over text, so we decided it could be quite a humorous endeavor to set up a date.
At our lunch date, my initial impression of him, unfortunately, wasn't too promising. He was somewhat socially inept and felt somewhat overbearing. Nevertheless, he seemed decent, so we settled down for pizza and began to familiarize ourselves.
In our conversation, I shared with him that I was pursuing a path in public policy. I was pleasantly surprised when he took a genuine interest in my specific focus area—this isn't something people usually pay attention to.
I passionately shared my interest in improving educational policies as I fervently believe that education holds the ability to significantly transform lives, particularly for the underprivileged.
After my fervent spiel, he dismissed it with, "That's interesting but I really don’t see the need for education for the economically disadvantaged. When I'm older, I'll want my household staffed with maids and butlers – somebody's got to do those jobs."
I sidestepped his comment with a diplomatic "Everyone is entitled to their own views" and began brainstorming ways to wrap up the date. Little did I know, the worst was yet to come.
Once we’d finished our meal, I thought of an excuse to depart an hour earlier than I’d intended. He seemed disappointed and jokingly said, "I ought to just kill you and keep you here with me." Insensitive. I admonished him that it wasn't really a good idea to jest like that. His comeback? "I’d hide your remains right there, haha."
Needless to say, I flagged down a taxi right after that.
50. Just Pop A Squat
I found myself in France, sharing a delightful evening meal at an outdoor cafe with a woman I'd just met the day before. But in the blink of an eye, things took a crazy turn.
She politely excused herself to use the bathroom, stood up, walked a few steps away, dropped into a squat, and proceeded to urinate right there in the street gutter. Needless to say, there was no second date lined up after that.