Ah, dating. We get all dressed up, do our hair, maybe put on a little makeup, and head out into the world hoping we’ll meet our soul mate sitting across from us at a table. If we’re lucky, maybe that actually happens—but most of the time, disappointment reigns.
1. Coming On Strong
He asked me to meet him in this bar, tucked away in a strip mall, the kind of place just for drinks, not meals. We were meant to be having dinner. I had spent time getting dressed up, doing my makeup and such. My heart sank when I laid my eyes on him.
His jeans were torn and his hoodie splattered with paint. It was in that second I thought, "Oh boy, this might be a disaster". But, I had already walked into the trap, so to speak. We took a seat, and without even taking my order, the bartender poured him his usual tonic in a pint glass. It was obvious he frequented here.
We tried to strike up a conversation, but he was just too... strange. He kept interrupting me mid-speech with irrelevant remarks, playfully hitting my arm, and constantly rushing me to finish my drink to keep pace with him. I just had a single light drink, which I paid for, much to his annoyance, and then decided to head out. But things took another twist.
He downed his final drink quickly, flung a $100 bill onto the counter, and trailed after me into the parking area. I tried to politely get out of the situation, but he blurted out, "Come over to my place. I go like a racehorse".
I fumbled out a "Uh, no thanks," but he was already behind the wheel, revving the engine and speeding out of the parking lot, almost tipping his car in the turn. The world of online dating was full of fascinating folks back in its infancy. Truly, 2004 was a modern-day wild west.
2. Too Close For Comfort
Here's my tale about dipping my toes into the quirky dating pool. I had this brief encounter with a girl—a friend's acquaintance. She once sauntered into the bar where I had a job during a $10 steak night event, accompanied by her mum and a guy who kept us guessing—boyfriend or brother?
It was revealed later, he was indeed her brother, but their bond was oddly intense. We finally went out together on a date, but she appeared horribly uneasy all through our time together. The conversation went absolutely nowhere and her disinterest was palpable.
Regardless, after the date, I drove her back home. She then extended an invite to step inside. Throwing caution to the wind, I decided to tag along. Their living room had two couches. I found myself uncomfortably perched on one while she opted to cozy up and spoon her brother on the other. That's when it hit me—maybe I shouldn't have come.
After this weird encounter, every time she left the bar, she always tightly clutched her brother's hand—always.
3. Doing An Ex A Solid
I connected with a woman on Plenty of Fish. As we chatted, we discovered she knew a colleague from my past. I inquired about her, and he claimed she was decent, not unhinged—turns out, this was a spiteful scheme. Apparently, he harbored resentment toward me due to my superior performance at work and had decided to deceive me.
We decided to meet for coffee halfway between our homes. She lived just 10 minutes away from the nearby mall where we arranged to meet. Upon my arrival, I spotted a woman who was significantly chubbier than her profile picture, pushing a baby stroller.
She joined me nonchalantly, as if strolling in with a baby was expected—even though she had mentioned having a two-year-old daughter. Interestingly, I had shared that I too had a two-year-old son. Then a surprise—her "two-year-old" was barely two months old. This glaring discrepancy was never addressed previously.
Moreover, she promptly asked me to purchase baby formula for her. Glancing at her, I realized she was genuinely in need, so I purchased it. I wasn't about to let her child go hungry. Maintaining my composure, I politely expressed that I couldn't continue our relationship due to her dishonesty.
She acknowledged this and departed. However, the drama didn't stop there. A couple of months later, I found myself conversing with another woman on Plenty of Fish, who happened to be acquainted with my previous date. This new woman seemed ordinary, unlike the suspected eccentric from the first debacle.
My past date (who had kept tabs on me) phoned me, warning me about the supposedly volatile nature of my new interest. Skeptical, I dismissed her warning, leading to her abruptly ending the call.
Shortly, my inbox was bombarded with videos and news reports sent by my past date, revealing my latest interest in the midst of a mental breakdown, setting her ex's car alight—all captured on a mall security camera. So, thanks to woman #1, I evaded an even greater disaster with woman #2.
4. A Blank Slate
I once went on a date with this guy who, astonishingly, had no hobbies whatsoever. Seriously, he wasn't into movies, TV shows, music—nothing. And he didn't have siblings, friends, or a job either; he seemed to focus solely on his university studies. Activities as basic as cooking, cleaning, or even taking a stroll didn't appeal to him.
I can safely say it was the most awkward social encounter I've ever had. He was pursuing a degree in Economics and lived by himself, completely jobless. We connected on Tinder, and his profile pictures along with our initial conversation painted a picture of an average individual. I shrugged it off as him being timid. Boy, was I wrong.
He was, hands down, the dullest person I've ever come across.
5. You Again
A few months after parting ways with my college sweetheart, I decided to dip my toes back in the dating pool. I matched with a seemingly interesting girl on Tinder and we exchanged a few messages. However, one peculiar warning sign came up. She was overly interested in my ex and my feelings post-breakup.
Despite this, I decided to let it slide and set up a dinner date with her. This, unfortunately, was a colossal mistake. So, I walk into the restaurant and guess who's waiting at the table reserved under my Tinder match's name? My ex.
I pivoted to make a quick exit when a chilling message from my supposed date on Tinder popped up saying, "You'll never be able to get away from me". With hindsight, I should have stayed home that evening and should definitely keep a wide berth from blind dates in the future.
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6. Seeing The Light
So, I ended up going out with this dude I met on Tinder. The connection? He works with one of my buddies. I thought, "Hey, he can't be all bad then," and gave it a shot. Our first rendezvous was pretty okay, so we decided to meet again.
Everything on our second outing was running smoothly until the moment I pointed out his pentagram pendant. I casually asked him if he wore it for the look or if he was a follower of Paganism. Wondering why I hadn't noticed this before, I figured either he didn't flaunt it during our first meet or it was just hidden under his clothing.
Upon hearing my query, he confirmed he’s Pagan. I expressed my fascination with Paganism and wished to know more. Boy, I didn't expect what was coming. The rather quiet guy I was getting to know did a full switch, launching into a wildly passionate speech.
He regaled me loudly in a fairly upscale eatery about his mom's unique healing capabilities and his friend's painless gunshot wound experience, thanks to their mental link across continents! I was like, "WHAT IS HAPPENING??" I somehow survived till the end of the date, and once I was home, I texted him nicely.
I told him that I didn't feel the spark after a couple of dates and I wish him the best. The response? A swift block. Noticing this, I texted my buddy—you know, the one who works with him—asking if this Pagan spiel was a regular occurrence for him. I couldn't believe his answer.
He started laughing and explained how everyone at work knew about Mr Tinder's unique behavior. Apparently, they knew he was harmless but quirky and were curious to see my reaction. A bit of a low blow from my buddy, right? He knew I was seeing this guy and could've given me a heads-up.
Anyway, no harm done and I'm just glad there won't be a third outing.
7. Three’s A Crowd
So, I bumped into this girl at a local pub and we hit it off pretty well. We decided to meet up for a date a few days afterwards. To my surprise, she came along with her "sister".
I didn't overthink it then—I just figured she wanted some safety, especially since we'd only just met. However, the same thing happened again, not once but twice. Eventually, I asked her if we could hang out without her sister around, and oddly, she seemed taken aback by the suggestion.
After a few months, I learned the truth. She didn't even have a sister. It was just her close buddy who was always by her side. Gotta say, it was extremely weird.
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8. The Only Living Girl In San Francisco
We'd attended the Burning Man holiday gathering since I volunteer and thus received an invite and a couple of beverage tokens. However, she was not a fan and persuaded me to whisk her off to a lovely eatery nearby. This cozy spot was located in the Dogpatch district.
Over time, the workers there began to develop a dislike for her and express concern for me. She wasn't really impressed with anything and barely acknowledged the staff. After I drove her home, she claimed I was a cult recruiter, which just didn't make any sense.
Regardless, I asked her out once more for reasons I'm not quite sure of. When I arrived to pick her up for our second date, she’d totally forgotten about it, so we ended up at a nearby sandwich shop. There, she started talking to another guy right in front of me.
My interest dwindled when she started passionately ranting that she was the only San Franciscan against aggression. I politely disagreed with her—but her reaction was wild. She just abruptly turned away from me and left. Why does this always happen to me??
9. Secret Messages
While still on our date, she sent me a text apologizing. Here's the rundown: she showed up late, then her pals "coincidentally dropped by" and tagged along. It was pretty clear their plan was to have me foot the bill for their drinks, which they started downing as fast as the waitstaff could serve them.
Catching on to their scheme, I took care to pay for my own drinks in cash thus avoiding any bar tab. I tried to cut my date some slack, hoping her friends would take a hint and depart, leaving us to our date. But, she seemed more occupied trying to impress them.
At one point, she was engrossed in her phone, then out of nowhere, my phone started buzzing. Normally, I wouldn't check my phone mid-date, but given the circumstances and the fact that she was also on hers...I thought, why not?
Looking at my screen, I found a text from her, reading just "Sorry". I glanced at her, then back at my phone, then I just shrugged it off. Full of indifference at this point. When I rose to take my leave, there was a collective gasp. One of her friends caused a fuss because I hadn't covered the bill for the group.
I retorted, "I've handled my own tab". Then I just strolled right out.
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10. He Almost Fooled Her
I went out a few times with this guy who appeared generally nice. Around the third or fourth date, he asked me to go tailgating with his family, who were strangers to me. I agreed, since I've never experienced tailgating before. Soon, I realized I may have made a mistake saying yes.
Visiting his place, he led me into his room, which was in quite a state: no bed frame, no sheets, food crumbs littered about, clothing half-folded on the ground, dim lighting and a carpet so grubby it felt hard underfoot. Totally gross.
His family turned out to be nice, but when it was time to leave that night, he behaved like a sulking child and first declined to drive me back. Looking back, I really should have driven myself. During our journey home, he started talking about his plan to spend $10k on an engagement ring and his longing to marry me.
Then came the news that his ex-girlfriend's father had threatened to involve the authorities if he didn't stop bothering her. The very next day, I sent him a text saying it wasn't going to work out. I had to block him after he sent me some inappropriate messages, claiming he was "just trying to get a reaction" out of me.
It irks me that I missed all these warning signs during our earlier dates.
11. Dr. Jekyll And Mr. Hyde
I once matched with a guy on Tinder who seemed really interesting. Fast forward to a month of exchanging text messages and we decided to finally meet in person at a local pub. The venue was packed that evening, so it took me a while to spot him. When I did see him, he appeared to have had a few drinks, but wasn't totally gone, he seemed alright.
In the loud and bustling environment, I attempted to engage him in conversation.Despite having initiated the meet up in this new place to me, and being just a breath away, he had difficulty grasping my words or responding to my questions. This was meant to be our first date.
He then orders me a drink and starts smacking my backside, rather harshly to be fair. He buys me a drink and soon after, surprisingly, he repeatedly asks me, "Do you want a drink?" The alarm bells started ringing at this point. I reminded him that he had just bought me one.
He kept repeating this question, seemingly forgetting that he'd already asked multiple times. This carried on for an hour or so. During this time, I sought to embrace the situation. I tried to play some of the pub games, attempts at making the most of the date.
His repeated question was, "What are you doing here?" My baffled response was always the same, "I'm on a date with you?" He kept revisiting this question too.I found it puzzling that he was so disjointed. He hadn't appeared heavily loaded and the texts before we met had been quite normal and kind-hearted.
However, all through the night, he just inquired the same two or three things, over and over, and continuously smacked my backside. At some point, we were supposed to join his buddies. I took advantage of the jam-packed crowd to leave. His behavior had been absolutely troubling and strange.
Later, he had the audacity to call me, questioning my whereabouts. I informed him that I had gone home. He expressed a desire to get to know me, and I replied, "maybe another time". I thought to myself, you had your shot all night, but didn’t seize it. He showed no signs of serious efforts. After that encounter, I blocked him without a second thought.
12. Honesty Isn’t Always The Best Policy
We had a fantastic dinner and went for a casual post-dinner stroll in the park. We enjoyed good conversation as we walked. Unexpectedly, she revealed something that took me by surprise. She confided that she was officially engaged to another man, but had only agreed to marry him because she had become pregnant.
She went on to share that she had recently experienced a miscarriage, something she hadn't informed him about yet. Now, with no baby in the picture and our burgeoning relationship, she planned to break the news and end things with him. Needless to say, we didn't go on a second date.
13. Don’t Follow Your Dreams
During our date, he launched into a tedious monologue, criticizing my job as an assistant welder. He called it "meaningless" and advised me to pursue a career in dental hygiene—something I have zero interest in—simply because he believed it had "better prospects". That date was HORRENDOUS overall. It was then that it hit me—we were anything but compatible.
14. Never Gonna Get This
I had a no-show for a date once, and I've never been more thrilled to have listened to my hunch. I was set to meet a fellow at a pleasant location downtown that we both agreed upon. But then he dropped a last-minute change—we were to meet at a different venue.
A quick search revealed the place was a somewhat shabby bar situated amidst seemingly endless fields. Red flags immediately started waving in my head.Despite really liking the guy, I knew I had to listen to my gut. So, I tried to call him, only to be greeted by his voicemail.
I left a polite message, apologizing and suggesting we reschedule, promising that this time I would be the one to choose the venue. The warning signs didn't let up, so when he returned my call, I let it go to voicemail. I was simply grateful I didn't pick up the call because his response gave me goosebumps.
I played the message back a couple times just to make sure I wasn't hearing things. The mature man I was excited to meet was suddenly hurling insults at me in an outburst of anger, even resorting to calling me a witch. Amid his rant, he expressed how fortunate I was to have missed out on the best date of my life with the best guy ever.
That’s when I knew I had made the right choice in trusting my instincts and skipping that first date.
15. A Lie Of Omission
The strangest date I've ever experienced? Likely, it was the time she concealed the fact that she was a mother. She conveniently left that out of our text conversations in the preceding days. However, that wasn’t the primary issue. The real deal breaker was her being a mother coupled with an inability to control her drinking problem.
To top it off, she subtly hinted that her ex, who happened to be behind bars at that time, hadn't officially broken up with her. It gave me the impression she was just stringing me along as a backup option.
16. Now Let’s Talk About Me
I can't pinpoint the exact moment when it hit me that coming on this date was a mistake, but the feeling struck me somewhere in the first 10 minutes. She arrived half an hour late, then shrugged it off with, "Sorry, I'm always late".
To make matters worse, she started the conversation with a fifteen-minute monologue about her recent breakup from three days ago. That's when I knew things were headed downhill. Throughout the date, she made no effort to get to know me, choosing instead to focus solely on herself and her issues.
She chatted about the antics of her friends—none of whom I was familiar with. Then, she spent a solid 20 minutes showing me all the pictures and videos of her cat. Normally, I wouldn't mind but by that time, I was more than mildly irritated.
She actually had the audacity to complain about the ice in her soda. And for the final ten minutes, she babbled on about needing to use the bathroom, but then refused to use the public restroom. When the night finally ended, I was so relieved.
17. Am I Bothering You?
I had a movie date, which seemed initially fine. After the film, we decided to go for dinner. However, straight away, my date got engrossed with her phone unlike anything I've seen before. After a couple of uncomfortable silent minutes and uneventful small talk, I politely asked if she was busy or if she needed to leave earlier.
"No, I'm okay," she said, "just staying updated on my social media and juggling a few chats. That's how it is". Well, I didn't relate at all. We had already ordered food though so I just remained quiet for the upcoming 20 minutes until it got unbearable for me.
At that point, I politely said, "Excuse me," and asked our waiter to pack my food for takeaway. I sat in the waiting area, but she never once looked up from her screen. I paid the waiter for my meal and made my exit.
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18. The Wrong Kind Of Double Date
We had reached about the halfway mark of the movie, when she mentioned she needed to take a bathroom break. What surprised me next was seeing her return with her boyfriend, whose existence was unknown to me till that moment.
Unexpectedly, he sat right between us and they started to make out, leaving me sitting awkwardly on the side. Without uttering a goodbye, I just up and left, heading straight home.
19. A Mountain Of Lies
I once met this lady who couldn't stop talking about her love for mountain biking. Seeing that as a common interest, I asked her if she'd be up for a mountain biking date, to which she agreed. A few days later, we were on our way.
As I picked her up, her roommate threw me a knowing look that seemed to say, "Good luck, buddy!" I got the feeling from her words and expressions that this date might not go as planned. Once we hit the biking trail, it didn't take more than five minutes for me to realize that she was definitely not as into mountain biking as she claimed.
To say the least, she sulked through the entire ride. When the ride was over, I dropped her off at her place. She casually mentioned, "I had a good time," which left me incredulous. Was she even on the same date as I was? Needless to say, there wasn't a second date.
20. Child’s Play
Something strange happened when he found out I worked in childcare. He kept talking about children and infants with unusual enthusiasm. Then it took an even weirder turn. Gradually, he expressed his desire to have a lot of kids and for me to stay at home to care for them.
I don't mind the concept of being a housewife, but his demeaning approach wasn't appealing. At some point, he even mentioned he wouldn't take part in parenting until the children were toilet trained, implying that would solely be my responsibility.
That's when I realized I'd made an error in judgment. The issue was that he was my only way home since a friend had dropped me at his place. I had no choice but to ride back with him.
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21. Getaway Car
She requested that we swing by her mother's place, as she had to "pick something up". After I spent ten minutes idling the car, she came bolting out the door, with a baby in her arms and a woman—yelling loudly—hot on her heels.
She threw herself into the car and started to shout, "Go, go, go!" I knew exactly what the situation called for. I turned off the engine and stepped out of the car. Turns out, the child was hers, but she had surrendered custody to her mom due to her struggles with addiction.
We had connected online via a dating platform and she assumed I'd support her scheme to reclaim her child. That night, she ended up behind bars.
22. He Should Have Watered Himself Down
He strolled into our designated meeting place, a quaint café, lugging along a 4L jug of water. He marched up to the counter, unloaded his jug, and requested that the barista brew his tea using his particular brand of filtered water.
Turns out, he peddles these water purifying machines that tweak the pH level, a venture he adamantly denied was anything close to a pyramid scheme (it absolutely was). I sat through his excruciating sales spiel, only for him to confess that his previous career was in dealing illicit substances.
He claimed he transitioned to water sales because of his "selling addiction". But that wasn’t the worst part. Then came his revelation of his “deep-rooted traditional beliefs," as he put them. He admitted to being a highly domineering individual and acknowledged his inability to change. His big gripe? Time-wasters.
In his quest for a wife, he detested any disregard for his time. Each time I attempted to engage in a conversation, he would bluntly interrupt and shift the focus back onto himself. He insisted on offering me a drive home after our encounter. I declined as politely as I could and made a discrete dash the moment I was out of his view.
23. Dads Always Know Best
About a quarter of an hour into our meal, he started going off on a politically charged diatribe. It caught me off guard when he declared, "If only minorities would put in more effort, their situations would improve. It's not like opportunities just land in white people's hands".
I quietly excused myself, ducked out to the restroom, then swung by the hostess stand to settle my share for a meal I hadn't even had the chance to enjoy, before exiting the restaurant. Once home, I shared the episode with my dad.
In the comforting manner dads have, he whipped me up a mouth-watering grilled cheese sandwich and gave me a reassuring hug. He advised that I should have stuck him with the entire bill. Though I kind of agreed, I just couldn't bring myself to do it, my own nature getting the better of me.
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24. Don’t Just Be You
A few years back, I took my first shot at online dating. It was a total flop. The woman I matched with was really lovely and seemed stunning from the photos she'd shared with me. From our conversations, I knew that she claimed to be 5’2, physically active, and had an average to slim figure.
I didn't question her height as it's tricky to gauge from pictures, especially since she asked mine. However, her saying she was fit and slender seemed unnecessary as it was evident from her photos. After chatting for a few weeks, we planned to meet at a park near a gazebo she suggested.
But when I arrived, all I could spot was a fairly tall, heavy-set lady standing inside the gazebo, dressed in pajamas. This woman towered over me; she had to be around 6’4” or 6’5”. Thinking she hadn't arrived yet, I called her. To my shock, the tall woman's flip phone started to ring. It was her.
After answering with, “I see you,” she immediately ended the call and began striding towards my car. At that point, I realized that my hour-long drive had been for nothing. Before she could reach the door, I locked it and rolled down the window, asking, "Do I know you?” All she responded with was, “Yeah, I’m a bit taller than I said".
After politely apologizing, I made a quick exit. Lies, especially easily verifiable ones, are a huge red flag for me in the beginning. Not long after, she sent a text expressing that it wasn't fair for me to leave her after she'd prepared for an outing. But her version of "ready" was worn-out, unwashed pajamas.
Luckily, I spent the rest of the day reconnecting with old pals who were nearby, so it wasn't a total waste. Dodged a bullet there!
25. When Dating Is Free Therapy
She was a self-confessed kleptomaniac. At first, I wondered if she was over-exaggerating or simply going through a rough patch. Then she presented an enormous stack of legal documents. Surprisingly, she was familiar with the judge due to her frequent court appearances.
She then asked me to feel her back, mentioning she was extremely sweaty from taking her MCAT exam. She also revealed her method of needle disposal because she was battling addiction. In retrospect, I should have distanced myself earlier, despite the sweetness in her.
Clearly, what she needed was professional help from a therapist, not a relationship.
26. Putting Out The Wrong Signals
I had a coffee date with a girl who seemed really charming and attractive over our text conversations. However, when we met up, things were quite different. She resembled her photos a little, but I couldn't help but notice her visibly decayed teeth and unpleasant body odor. Additionally, her breath was extremely off-putting.
On top of this physical unattractiveness, she acted pretty peculiar. She wasn't impolite or unkind, but I felt her personality lacked substance or uniqueness. What truly turned me off was her poor hygiene, which I found quite distasteful.
As our date came to an end and we were heading towards our cars, I gave her a polite goodbye hug. To my surprise, she inquired when I was planning to kiss her. I tried to politely decline, stating that I don't typically kiss on the first date.
However, she was not dissuaded by this and initiated a kiss, even going so far as to stick her tongue directly into my mouth. She ended the night by saying she's looking forward to our next date, with an implied suggestion for more intimacy.
Afterwards, I sat in my car seriously reconsidering my dating life, while repeatedly chewing on gum. Her taste lingered in my mouth despite several attempts to rinse it out with mouthwash.
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27. Making Small Talk
Back in late 2011 to early 2012, when Plenty of Fish was still a big deal in the online dating scene, I experienced my second (and final) online date. I had been chatting with a woman whose profile piqued my interest. We shared common hobbies, and her photo made her look attractive, so naturally, I was intrigued.
However, on the eve of our meet-up, she confessed that her profile picture wasn't actually her but of a friend instead. She did send me a snapshot which only showed the top half of her face. Her eyes were lovely, though, and I empathized with the discomfort of sharing a full picture online, so I didn't cancel our date.
During our night out, I discovered that her face was rather pear-shaped. Her build was somewhat slim yet, unique because she was chubby in places one doesn't typically associate with being "chubby".
Over coffee, instead of discussing our shared interests like video games, music, and favorite TV shows as anticipated, she chose to vent about her mom and younger brother, particularly about how she was "unfairly" prompted to look after him the night before.
I attempted to shift the conversation topic, but she was relentless. We were both 21, yet her topics felt completely unrelated to our online chats. I called it quits afterward, informing her that we weren't a good fit. That same evening, I removed my profile from the dating site. From then on, online dating was a no-go for me.
28. Food For Thought
I was meant to retrieve him from his Airbnb for a dinner and drinks rendezvous. Shockingly, it turned out to be his folks' home. I found it peculiar that he fibbed about his exact location but assumed he was just mortified, so I didn't fuss over it. His reply, when I recommended a spot for dinner, gave me a really eerie feeling.
He disclosed that his parents had cooked dinner, hence his preference to dine at home and maybe hit the bar later. The idea of having a meal with his family on our first date seriously unsettled me, but it escalated. He dished up a plate for me, directed me to a table in the garage, and promised to return promptly.
Then, he disappeared inside to feast with his family while I was isolated in the garage. I wish I could claim that I abruptly exited, but sadly I endured what ended up being the most appalling date night of my life.
29. Crazy Cat Lady
My disastrous date: I unfortunately indulged in too many drinks before my date arrived and chatted excessively about my beloved cat. I ended up coaxing him to come inside, despite my initial plans to keep the date out. Upon disrobing, my cat-themed undergarments were on display, much to his amusement, bolstering my eccentric cat woman image.
Following an unimpressive intimate encounter, he fumbled to find his clothes, only to discover my cat nonchalantly seated beside his clothes, now tainted with discernible cat urine. Definitely a tough night for the chap.
30. Getting Back In The Game
This is a story about a buddy of mine. After breaking up with a long-term girlfriend, he wanted to start dating again but without spending money on a dating app, so he stuck to the free ones. He arranged for a girl to come over to his place for a hot tub date. The girl showed up and asked for a specific drink, lets say goldschlager, which he didn't have.
She insisted they get some from the store. She seemed a little shady, so my buddy, suspecting he might get robbed, decided to leave his wallet and phone at home and asked her to drive. To his surprise, her car had no passenger seat because she has a big dog and had removed it, so he had to sit in the back.
The hour was late, so the closest store was closed. She suggested she knew another store which was open late, ignoring his argument that state stores all close at the same time. As they hit the highway, he started to get worried about where they were headed.
When he asked, "Where is this store?" she screamed, having completely forgotten he was in the back seat. He realised then that she'd already had quite a few drinks. She refused to stop or let him drive. The late-night store ended up being a half-hour drive from his house, during which she forgot about him in the backseat twice more.
As he had predicted, they arrive to find the store closed. She flipped out, started tugging at the locked door and yelling "HELLO!" repeatedly. He watched her from outside the car as she began yelling at some dubious-looking guys drinking in the parking lot. She began asking "why is this store closed" and quickly moved on to swearing.
My buddy took advantage of the situation, walked away and didn't look back. Now, he was stranded a half-hour drive from home, without his wallet or phone as a result of his own "brilliant" plan. Eventually, a sympathetic convenience store clerk let him call his brother to come get him.
He worried the girl might show up at his house, but she never contacted him again.
31. Off The Deep End
She was speeding through rain, heading away from our planned destination. As she shared her mental health history—of her parents' insistence on psychiatric care that she refused to comply with—I managed to persuade her to eat dinner at a local Chinese place instead of a coffee shop. Shortening our evening seemed like a good idea then.
After dinner, I needed to head back to my car as my mom was visiting. But in the parking lot, she argued that I should spend more time with her instead of my mom who's been in my life forever. Ignoring her calls didn't help—she began stalking me for months. She tailed me around town, even when I was just running errands.
Unexpected visits to my house, midnight knocks on my window, leaving meals at the doorstep, and leaving sweet notes on my car became a norm. I was on the verge of placing a restraining order, but after an incident where I had to physically drag her away from my home, my roommate's stern warning deterred her.
She took her obsession to a more manageable level—and limited herself to stalking me on campus.
32. Shooting His Shot
So, I connected with a girl on Tinder (I'm also a girl). We'll name her Cecelia. Our plan was to catch up over a cup of coffee, aiming for a slow, relaxed first interaction that goes against the "U-Haul" stereotype. Upon arriving, a guy approached me. "Are you Kate?" he asked. "Yes, I am," I replied, "I'm Brent," he said, "I'm Cecelia's cousin".
I asked why Cecelia hadn't been able to join us. "Actually, those were my photos you saw. You were chatting with me on Tinder," he admitted. "But why?" I wondered—and his response really stunned me.
"You see," he begins, "straight girls tend to be judgmental. So, I thought it might be simpler to try and 'convert' a lesbian. You liked me when you thought I was Cecelia, so why not give it a try?" Needless to say, I didn't give it a try.
Later, I managed to find the real Cecelia through social media and informed her about Brent's actions. Regrettably, Cecelia wasn't actually a lesbian, and I'm still single. Adding to this saga, my most recent two dates only wanted to discuss astrology and cryptocurrency, respectively.
33. The One That Got Away
A guy once invited me out for lunch. That day, I put on a nice outfit to make a good impression. I met him at his workplace on my lunch break. We found ourselves in a messy combined break room and storage area, where he told me to take a seat on an upturned bucket. He started to whip up a bag of microwavable cheesy pasta.
He served up this lukewarm mush in a disposable foam bowl. During our meal, he spent the whole time reminiscing about his ex, who was as beautiful as a sculpture from the Renaissance era and penned admirable poetry. Fast-forward a few years, I ended up becoming friends with his ex.
When I shared our unconventional "lunch date" story with her, she was taken aback and quite embarrassed.
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34. She Didn’t See This One Coming
While using a dating app, a lady, who said she was 35, struck up a conversation with me. I relished our delightful chats. In time, she proposed we meet for dinner and see how things evolve. I drove to her place to fetch her, and as I bided time in my car, a woman in her mid-60s approached. That's when I started to get a bad feeling.
Her introduction matched my chat partner's, yet when I queried her age, she kept repeating it was 35, a claim that seemed farfetched. She waved off my request to verify her age from her ID and pressed for us to proceed for dinner. Nevertheless, I underlined how honesty stood as a cornerstone for every friendship or relationship.
However, her insistence on being 35 remained unwavering. Even as I was driving towards the eatery (actually going in loops), I strove to get to know her better. Our conversation received an interruption from her work call. She asked me to stop the car so she could handle it.
She stayed inside and I eavesdropped on a spectacular revelation. She worked as a phone psychic. She was providing assistance to a distressed lady, informing her about the rate system; it started with a $10 charge for the first minute, escalating thereafter.
Post conversation, she cheerfully proclaimed, "Easy $12". Then, I hit the road again, this time rerouting back to her place, unbeknownst to her. As our chat about her life continued, she accidentally let slip about her 31-year-old son. I burst out laughing, saying, "So, you became a mom at four?"
Caught in her weave of lies, she tried to backpedal but by then, my car was parked in front of her house. I requested her to get out, stating that dishonesty was uncompromisable.
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35. Game Night Gone Wrong
A so-called friend suggested that a colleague of hers and I would hit it off, and proposed a double-date at a festival with her and her spouse. My date-to-be proposed that we should get acquainted the night before at a bar, one that offered video games—an idea I instantly warmed up to.
When the date night arrived however, he was nowhere to be found. He finally appeared, late, with an excuse about having to stop by his place to let his dogs out to avoid any potential messes. He then presents me with a photo of a floor smeared in dog poop and says, “Guess that didn't go as planned".
He’s still in his work gear, despite having had three hours to freshen up after work when he went home to attend to his dogs. He goes on to polish off the charcuterie platter I'd ordered without a second thought, before ordering some wings just for himself.
We eventually decided to try out a game, as I had purchased extra game time. He initially suggested a shopping-themed game that wasn't really meant for two. We compromised on a game, though it wasn't the best choice.
As we were winding down, he casually mentions that his previous date ended up being a parking lot rendezvous. He stares at me, clearly implying a repeat performance. I quickly let my friend know I won't be attending the festival. My date, inexplicably, seemed surprised; he assumed we had chemistry.
36. All Over The Shop
He picked me up a bit early and let me know via text he had arrived. So he definitely had time to tidy up the front seat of his car. Unfortunately, it looked like a bookstore for right-wing literature when I opened the door.
He saw my eyes widen and quickly said, "Hope I'm not going to hear some wacky liberal opinions from you," as he swept the pile of magazines onto the floor. The encounter had me swerving into awkward town right off the bat. This was my first attempt at dating after a devastating breakup and it didn't get much better from there.
Halfway through the date, I was crying in the restroom. And believe me, the irony of his political joke versus his choice in car, a Prius, wasn't lost on me. Throughout the evening he seemed to have a knack for devaluing my interests.
When I said I enjoy scuba diving, he boasted about his breath-holding ability and mocked the need for supplemental oxygen when free diving. I responded with a noncommittal nod.
And when I admited to being a rather poor cook, yet didn't mind due my lack of pickiness when it comes to food, he romanticized his mother's "southern values" and insinuated I was missing out. At this point, he let off an underlying tone of sexism boiling down to outdated expectations for women.
Perhaps realizing we didn't exactly mesh well, he suggested his friends join us. Expecting them to be around our age, I was surprised when a group of 60 something-year-old fisherman showed up. Honestly, they turned out to be an unforeseen lifeline in a sea of dull conversation and lack of shared interests.
It painted a clear picture of why he didn't hang out with many people our age.
37. A Family Affair
It so happened that when I arrived, her closest friend was already there. No one had given me a heads-up that she'd be tagging along. But that was only the beginning. Following this, her brother turned up. Not long after, her father made an appearance.
Then her mother and three of her cousins between the ages of 3 and 5 joined the party. At that moment, I discreetly excused myself for a restroom break. THANKFULLY, this is the kind of establishment that offers a discreet escape for patrons in middle of an awkward date situation.
Apparently, I was the first guy they helped make an early exit.
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38. Fancy Meeting You Here
Before our inaugural outing, he had insisted he desired to make arrangements. Having brought up my several years-long vegetarian lifestyle, I stressed that regardless of the location, as long as it had veggie-friendly dining options, I wouldn't object. What does he do next?
He takes me to a steakhouse, confessing he'd disregarded my vegetarianism. So, I spent all evening snacking on fries. However, to his credit, it genuinely seemed like he inadvertently overlooked my preference, and our chat was engaging, so I was swayed into a second meet-up.
Presently, I'd also divulged my caffeine intolerance to him—no coffee, Coke, most teas, etc. Guess where we found ourselves next? At the campus coffee kiosk. Soon after, I skedaddled for my archaeology lecture, where my study partner informed me of an impending tutor change due to our current one falling ill. Can you guess the identity of the newcomer?
It was Mr Steakhouse turned Coffee guy. Even today, I'd say it was totally worth the experience, just for the sheer surprise on his face when he walked into our classroom. I really wish I were joking.
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39. Moving Fast
I once traveled 50 minutes to a quaint town for what I thought was a movie date. To my surprise, it was actually at her home, and the film was a sequel to a trilogy I hadn't even begun watching. The girl was somewhat awkward, which I could deal with, but then she began to overshare excessively.
She disclosed personal information such as her chilling past and that her mother was an addict. At that point, I realized the situation was a huge mistake as she had been less than truthful to secure the date. As the evening drew to a close, she put the nail in the coffin.
She actually expressed that she loved me. Bewildered, I decided to leave shortly after her confession and gently let her down via text when I arrived home. To top it all off, she fell pregnant three months later with her new boyfriend, who had been in her life for just five months.
40. Kind To Be Cruel
I was patiently sat on a park bench beside a girl for nearly half an hour past when I was meant to meet my date. Turns out, I'd been next to my date the whole time. I just didn't recognize her, as she was significantly larger than she appeared in her photos and did not resemble them at all.
Apparently, her good-looking friend had lent a hand by creating a Tinder profile featuring her own pictures, carried out the matches and charming chats, and allowed her less appealing buddy to be the one present at the meetups. Her attempt at helping out her friend wasn't quite successful.
41. Joking Around
After a couple of encounters at my neighborhood store, I decided to join this guy at his house for a game of Magic. When nature called, I excused myself to use his bathroom—that's when things took a rather grim turn.
He positioned himself outside the bathroom, doing a rather eerie rendition of the Joker's laugh while expressing sentiments that seemed very peculiar. He said he's been waiting for someone like me and made other unsettling comments about how I am "perfect for him".
The moment I concluded my bathroom duties and stepped out, oh boy, the awkwardness was palpable. Trying to alleviate the situation, I repeatedly praised his Joker impression and giggled nervously, but he persisted with the Joker act.
That subsequent walk down the stairs was probably the lengthiest and most tension-filled moment I have ever had to endure. I made my exit soon after that. The experience continues to unsettle me.
42. Only One Woman For Me
He shared that he misses his mom and tears welled up in his eyes because the music brought back memories of her. She's not gone, however, she just wasn't present with us at the restaurant.
43. Tell Me How You Really Feel
When she posted on Twitter about being on a date and revealed that she didn't feel like being there... this happened right at the start, while the date was just beginning.
44. Dress The Part
The moment I stepped into the restaurant where I was scheduled to meet a "Doctor" marked the most disastrous date I've ever experienced. I first connected with him online, only to find him at our rendezvous spot, donning a white lab coat... to a dinner date... our very first and, definitely, the last one.
45. From A Yes To A No
He popped the question—would I go out with him? I happily said yes. Then came the inevitable question about dinner, specifically, which cuisine I favored. I was pretty open, except for sushi. Yet, guess where he decided to take me? Yup, a sushi joint. He was sure he could sway my dislike for sushi.
46. A Real Winner
I once proposed a Tinder date meet me at DC's Hirshhorn Museum. He arrived and declared, "I despise art". However, he ironically proceeded to poke his fingers at every artwork until museum security spotted him.
47. Disappearing Act
We swiped right on Bumble and things clicked instantly. She suggested carrying on our chat on Snapchat, to which I agreed. We were constantly engaging, and I went on to invite her out to dinner later in the week, to which she gave a gladly positive response. Instead of us meeting halfway, she recommended a cosy Italian joint in her locality.
I didn't object and our conversation carried on smoothly until the day of the anticipated date. Given we were swapping snaps, there was none of that catfish business. We acknowledged the genuineness of our identities in advance. Thus, on the day of our date, I find myself undertaking a 55-minute drive to her town.
We met at her preferred dining spot, displaying our excitement with dinner table chuckles. Upon sitting, the server arrives to take our beverage orders; we both choose water. I sought her advice on menu favourites since she was a regular. She suggested a few items, even sharing her own choice.
To avoid distraction, I opted to try her proposed dish. We dive into discussions about work-week dramas. She's in cyber-security, which brings about the question of how she ventured into such a field. Our chat spins around her academic background and flips to mine, revealing my full-time grad studies and part-time security guard gig.
A light-hearted joke on our shared relation to security roles sparks a shared laugh. Little did I know, there was a surprise in store for me. Our drinks arrive, and the server takes our meal orders. As he departs, she abruptly announces a restroom visit, leaving her belongings behind and exiting composedly.
I recall having friends and relatives preferring home bathrooms over public ones, so her wish for a nearby date venue made sense. About 15 minutes in, the server delivers our plates. Optimistically, I comment that she's temporarily stepped out and will be back shortly.
Some ten minutes pass before I indulge in my cooling dinner, attempting to check in with a text—"Hey, is everything okay?" Her delayed response is an easy-going "Yeah!" followed by a shocker of her not planning to return, accompanied by another one-word, exclamatory reply.
The oddness of this situation sinks in, stirring a mix of confusion and frustration. After my hour-long commute, I was facing the prospect of settling the bill for an untouched dinner. Doing my best to keep my cool, I text her, asking if she wants to reschedule and if something urgent had arose. She replies stating the absence of a spark between us.
Recalling that our pre-order chat lasted no more than 10 minutes and majorly comprised her career anecdotes and office gossip, left me perplexed. Why would she stick around to order, only to promptly make an exit? Regardless, I polished off my dinner.
Later, as the server cleaned up our table, I informed him of my unusual dine-out experience. He empathised with my situation over a free drink, and it turns out, he even took her meal off the bill. Gratefully, I tipped him the approximated cost of her meal. Thereafter, we lost contact completely, leaving me puzzled about that bewildering date night.
48. This Is A Girl Who Can Multi-Task
When I was 18, a girl reached out to me via MSN, saying a mutual friend had passed along my information. She wanted to go out with me. My friend vouched for her attractiveness, so after a chat, I decided to take her up on the date.
All I had to go on was one appealing photo. I arrived at the arranged café, but things veered off the script instantly. A woman I didn't recognize approached with a baby in tow.
She asserted that she was my date, even though she looked nothing like her photograph. She admitted to using a different photo since she didn’t think I’d accept her real appearance (she wasn’t wrong). But the surprises weren’t over.
She dashed off to use the restroom, leaving her baby with me. After waiting for her return for fifteen minutes, I sensed something was off and asked a waitress to check on her. The waitress promptly returned with a shocking revelation—the restroom was empty.
I scanned the café, but she was nowhere to be found. By then, she had obviously left unnoticed. Lacking her contact information and with no internet on my pre-smartphone, I had to rely on my friend to reach her on MSN.
My friend was just as taken aback as I was, as he too believed her pictures were authentic. Another worrisome 20 minutes slid by. I edged closer to panic, leading me to ask the waitress for help. She called the authorities, who arrived to assess the situation.
With only spotty information about the girl, I couldn’t offer any significant help. They instructed me to have her contact them if she reached out. Once released, I walked back to my car, passing by another café a few establishments down.
I was stunned to see her there, sitting with another guy. I rushed back to inform the authorities and deliver the baby. Parked outside and peeking through the window, I waved at her when she looked up. Turns out, I'd inadvertently become a babysitter for her actual date.
49. Emily Post’s Long-Lost Brother
As we skimmed through the menu, he asked about my choice of meal. I began, "Well, I'm considering..." but he interrupted and jested, "They don't serve WELL here". I laughed it off, persisting, "So, I suppose I'll choose the er...chicken".
Correcting me once more, he said emphatically, "There's no CHICKEN on this menu," and dismissed me with a condescending shake of his head. I was left just staring at him, incredulous.
50. Bait And Switch
So, I matched with a girl on Tinder. She greeted me with "Hi, fancy joining me at my parents' house?" We exchanged a few messages. She made it clear she wasn't interested in anything serious, just having a bit of fun. Though it seemed a bit too straightforward, I couldn't resist as she was attractive.
When I looked up her given address, I was seized by a feeling of unease. The location was in a familiar neighborhood that I had worked in previously. Even more disturbing, I recognized the house as one that was up for sale due to the original owner's demise. His children had intended to refurbish the place for resale.
With this knowledge, I was sure I was being set up, but my curiosity nudged me on to check it out anyway. Before I went, I informed her I'd be arriving in a different vehicle. The address was situated in an upscale, sea-facing neighborhood. With a sense of adventure, I drove my work truck there.
Upon arrival, a large man emerged from the house, eyeballed my truck, and went back inside, not before I noticed a handful of others in the house. Immediately, I hightailed it out of there. The situation just screamed scam. Maybe they planned to rob me or perhaps it was all a prank. Either way, I wasn't interested in sticking around to find out.
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Sources: Reddit,
