Disastrous First Dates

December 13, 2022 | Rachelle Horne

Disastrous First Dates


Everyone has experienced at least one bad date in their lives. From cringe-inducing creeps to full-fledged psychopaths, you never know who the person sitting across from you will turn into by the end of the night. The following Redditors shared their stories of bad first dates and they're so horrible, they'll make you want to stay single. Read on for some messy tales:


1. Bathroom Break

Being totally into my coworker, I was over the moon when she agreed to go out with me. But in less than a minute, the magic went up in smoke. While we were in some back alley, she said she needed to pee but did something completely disturbing instead.

She pulled down her jeans, pooped behind a dumpster, and used a newspaper from it to clean up. After that, I just couldn't keep the conversation going.

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2. Not In The Stars

Our first date happened at a sushi joint. She asked me about my zodiac sign. "Scorpio", I answered. Then, outta nowhere, she reached across the table and gave me a stinging slap. I was totally baffled and managed a "What...?". She just calmly said, "I NEVER date Scorpios".

I darted off to the washroom to gather my thoughts. By the time I returned, she'd vanished, but not before settling the entire bill. Whew, bullet dodged.

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3. Toe Thanks

I was excited to meet this dude at his home for the first time. I was really digging him...until I saw his living room. There was this gross heap of toenail clippings right on his coffee table - not just a recent trim, we're talking a collection here. He knew I was coming over! I high-tailed it outta there.

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4. Not A Gentleman

This dude and I were finally grabbing a bite after a few weeks of talking. Suddenly, he dropped a bombshell that I was never prepared for: "You know, for us to work, you'll need to mingle, right? My friends and I have a thing for sharing girls". I was speechless!

After stuttering a bit, I told him this wasn't gonna fly. I asked for a takeaway box and my half of the bill.

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5. Mutual Attraction

I was on my way to meet a blind date. As she opened her door and saw me, her first reaction was a disgusted "Ew". For some reason, I responded with "Yeah, I agree". Then, I just walked away. The whole date lasted less than five minutes.

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6. Dodged That One

I met this dude on a dating app. Guy shows up, eyes as big as basketballs, acting all kinds of weird. Told me he'd left his wallet at home, so I agreed to cover our first round. We then left for a second place, so we could meet his friends who'd lend him some cash. Important note: All the while, dude was rattling off pure gibberish.

I still figured, "Hey, maybe give him a shot," until he started sharing this freaky tale about chucking his ex's tiny dog in the pool and how it almost drowned. He was laughing the whole time. I knew then, I had to get out. FAST. Just as we were close to the pub, he gets a call. We were already 30 minutes into the date and bar-hopping.

He chugged his drink in record time while he handled his call. I grabbed the opportunity and told him I'd meet up inside the pub since it was just a few steps away. Anything to get a head start. And then I booked it right past the bar and legged it home.

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7. Made For TV

This took me to this Kumdo session on our first day - it's like Korean swordplay. Pretty neat, right? Except it was a high-level class, and I ended up looking like a total moron. Still, good times...until I discovered she'd been pretty sketchy. She didn't bring me just to hang out, but to be a part of this documentary about foreigners in Korea.

I was floored, but what could I do? I was already up to my neck in it. Next, we dropped by her boss's house for some makgeolli, and the whole crew started grilling me. They kept throwing us couple questions as if we'd been an item for ages. I guess they had no clue it was our first night out together.

So here's me, trying to dodge cringey questions without making us both look bad on TV.

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8. The Den

He asked me to chill at his place while he got ready. No sweat. When I got in, he really wanted to show me his "playroom". Aside from a TV and sofa, the apartment was basically empty. His room though, fully decked out. Already got my creep vibes tingling, then he really pushed it. I was totally grossed out by his next request.

Try on the handcuffs on his bed? No, thanks! Luckily, I planned a rescue call from a buddy at 30 min into the date and faked a crisis.

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9. Judgmental

I had to pick him up one night, and he was just nagging about every little thing - my car, how I drove, my song choices, even why I wasn't talking much. But what really got to me was when he said, "My buddies are dying to meet you. I gotta show 'em you're not imaginary". That's when I bolted.

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10. Not A Family Guy

He asked me and a friend to join a dodgeball game with his friends, whom I'd never met. Things were decent—I was kinda sidelining while he was focused on his mates. It was cool though, 'cause I had my friend there too. We were chilling in the parking lot, waiting for the game, when suddenly, dude aimed a ball at my waist and threw it full speed. He then hollers, "Smack, right in the jewels!"

I glanced at my friend, signaling it's time to go. I said my goodbyes then. Got home, saw my phone was bombarded with texts saying I was being "childish".

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11. One Thing After Another

I hit up a bar and vibed with this cute girl. She suggested going to her place, but some friends joined us at the bar. By closing time, they were all a bit wobbly and one friend was stubborn about not leaving her truck in the bar lot.

So, I said I'd drive her truck. We got nearly to their place but the parking was tricky. She wanted to take over (bad idea) and she pulled the "It's my truck" card so I gave in because, well, it was her ride. I never should have let her get behind the wheel.

Within a beat, she knew she messed up - backed the truck into a ditch and got stuck. We all ended up muddy, trying to free the truck, and in the chaos, the girl I'd met lost her wallet. I dived in the mud and water to find it. Back at her place, with the excitement over, we wound up eating deli stuff from Safeway on her kitchen floor at some ridiculous hour.

I crashed on her couch, woke up early, and thought, "She's cool, just the truck drama spoiled it". I looked to leave my number before I left. I couldn’t find a pen and paper...but what I did find was a court date notice pinned to her door for a domestic case. I split and wrote the night off as a weird one.

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12. My Crazy Ex-Boyfriend

Our date started with a nice, casual walk. The dude didn't pause his rant for an hour, trashing everything under the sun. He couldn't care less about me. It was miserable, and it was only going to get worse. We hit a restaurant, where he went ahead and ordered my food without asking. Dude shrugged off the bartender who warned him about the tight lid on his juice bottle. Tried opening it himself and ended up wearing the juice all over his shirt!

He goes off on the staff like it was their fault. I was mortified. Yet, he didn't care about yelling in public. Kept boasting that he'd fire folks like the bartender when he becomes a manager. Um, ok.

When it came time to pay, I offered to split the bill since he'd mentioned he was short on money. Clearly, I didn't wanna see him again and didn’t wanna feel like I owed him anything. Dude lost his mind, causing a scene again. I put money on the table and walked out.

He was still yelling when I left—then he grabbed my hand, telling me to wait up. When I suggested I grab a taxi, he insisted on walking me home to 'protect' me. To avoid a scene, I agreed. The walk was silent until I tried to break away, but he insisted on tailing me for 'safety' reasons.

I was freaked by this point but the worst was yet to hit. At my gate, he tried forcing himself on me, insisting I owed him because we dated, and he 'spent' on me. Pushing him off, I got a $20 bill thrown at me as he spat, "Here, we're done!" I scrambled in and bolted my gate shut.

He didn't leave quietly. I had to threaten him with the law to make him go. The kicker? His aunt was my neighbor and my mom knew his. The gall the woman had to ask how the date went the next day! I gave her a piece: "You should've raised him better". They ghosted me after. Suits me just fine.

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13. I Spy

We were hitting it off online and decided to meet face-to-face. He arrived with a lit-up Bluetooth headset on. Even during drinks, it was still on. I mustered some courage and asked him to remove it during dinner. His response was so much creepier than I expected: He confidently said, "No worries! You have all my attention. It isn't a phone headset. It's a camera".

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14. Expensive Taste

She was all about going to this super fancy restaurant on our first day. Once we were there, she went all out - a $25 starter, $45 steak, and a $15 drink. And she just wouldn't put her phone down, always on a call or replying to a text. The server clocked this and gave me a nod from behind her. Turns out, she had a plan.

When I made an excuse to get up, the server already had our bills split. Server asked if I wanted to pay for my stuff and bounce, leaving her at the table. And I was like, "Sure, that sounds perfect!" So, that's exactly what I did.

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15. If You Invite Two Friends

Rewind to high school, there was this stunning girl, Melissa, in some of my classes. Teenage pregnancy wasn't as prominent in the late nineties, which made her even more intriguing since she had a kid. But that didn't change how attractive she was to me.

Whenever there was an opportunity to be near her, I seized it. She needed help studying? I'm there. She wanted someone to chat with? Consider it sorted. But I lacked the confidence to ask her out. I was no Chris Hemsworth during high school, so it took ages to gather the courage to ask her. When I finally did, she agreed!

Our game plan was simple; I'd choose the dining spot and she’d take care of the entertainment. Then suddenly, our date night took a wild turn. She showed up with her sister. A clear red flag I should have availed to bail, but no, dumb ol' me just went along.

Post dinner, she had a 'surprise' for me which she was certain I’d love. As we entered a small convention center, I had no clue what I'd signed up for. Too late then, as it hit me like a ton of bricks when I saw the sign outside one of the rooms -- a pyramid scheme. Let's not even discuss the sense of drastic failure and misery I felt during the entirety of that lecture and gathering.

To top it all off, they didn't even sit with me. Being fashionably late to the event meant they found seats elsewhere while I handled the barrage of questions from strangers alone. Through the fog of my mortification and disappointment, I don’t even remember spotting Melissa or her sister at the event.

The night concluded with us back home where, with a straight face, she told me she had a wonderful time. I mirrored her sentiment, trying to be polite and bid her sister farewell. I never glanced Melissa's way after that.

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16. Thanks But No Thanks

We started talking online. Back then, I was a "pack-a-day" kinda person and I mentioned it to him. He didn't mind because apparently, he was also a smoker. Then we thought, why not grab a coffee at Starbucks? As I saw him for the first time, he greets me with "Hi. Just so you know, when I said I smoke, I was referring to crack". I was like "Oh. See ya!" and just walked off.

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17. Double Date

She glanced past me, and said, "Hey, my other date is here".

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18. No Game

He was late by about 45 minutes, but it was pretty crappy out, so I didn't care. We got to the cafe and the moment I removed my coat, he makes a cringey comment about my "A-game," or my "D-game", hinting at my bust size. It was so awkward that even the folks two tables down stopped to look at him.

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19. Pet Peeve

She took her pet rat along, chilling in her bra, munching on fries. She offhandedly mentioned having some warrants out for her, but not to worry because they were in other states. So, I pretended there was some urgent stuff I had to handle and bolted.

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20. Slashing Good Time

This dude showed up with two of his friends, totally outta the blue. They were all loaded. Managed to nab a waitress's attention while one of the guys ducked out. Just as I put my food order in, my blind date and his remaining friend told me they'd already eaten. Then, third-wheel-guy strolls back in and I nearly choked - dude's arm is gushing blood from some gnarly gash.

I high-tailed it to my car to get my first-aid kit and gave the wound a quick clean and butterfly stitch. Slapped on some band-aids and told dude to raise his arm while our waitress called an ambulance. Freshened myself up, and when I got back - I'm shook - date and his remaining friend had polished off my dinner. I pocketed my kit and purse and just bounced.

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21. Netflix And No Chill

She was just a mean person. Maybe she was having a tough day, who can say, but she made a comment I didn't appreciate. We went to this hip, affordable restaurant on a Friday night, and it was packed. All she did was complain about the service being slow and claimed they couldn't hear her over the noise.

She bothered other guests, but it wasn't smart or funny, just cruel and small. The last straw was a hurtful comment about how I looked. It might have been playful teasing to her, but it hit me hard. I quickly finished my meal and asked for the bill.

This awkward waiting time of around five to ten minutes followed. I got up, left enough cash to cover my meal and a big tip for us both. Given how she'd treated the staff, I knew she will not leave a tip. I then started to put on my jacket.

She questioned, "Cold much?" "No". "So, where to next?" "Home". She looked lost briefly, then smirked and replied, "Cool, Netflix sounds good". Realizing what she thought I meant, I clarified, "No, I meant I'm heading home...by myself". And, just like that, I left the restaurant and hit the street.

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22. Uncontrollable Urge

My buddy's friend and I went to grab a bite. While we were ordering, he started saying stuff like, "After I finish my food, you're next". I chuckled, thinking he's just messing around due to nerves. Then he asked the waitress for a strong drink.

I declined, mentioning I had to drive. He gave me a weird look and said, "You're not leaving after just one drink. You're staying the night". The waitress seemed shocked. Seeing this, I told him he had to knock it off. He apologized and calmed down, but that didn't last.

In no time, he was back at being creepy. Things like, "I can't hold it anymore. So we leave now, or get ready to join the table". I excused myself, went to the waitress, paid for our food, and slipped out without a word.

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23. Stalker

Things were going smoothly until one afternoon when we went bar hopping and hit a food truck festival. Weird thing was, the same guy kept showing up where we went.

When I tipped off a bouncer about the possible stalker, he politely asked the guy to leave. My date saw this, ran to the bouncer and dropped a bombshell - the 'stalker' was actually her husband! Turns out, they get kicks from watching each other on dates.

Needless to say, I bounced and reported them to the cops.

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24. Weird Pal

I was chatting with this dude who's a math professor. He asked me out to some open-air show where he was the "star". When I showed up, I realized it was a church picnic, and he was playing Satan. He introduced me to his fam, who were all obsessed with Weird Al - like, they wouldn't listen to anything else.

His sister then decided to grill me about why I went to a private school. What I didn't know was that he'd spilled all the beans about me - every chat we'd ever had. To escape, I pretended there was an emergency. Later, he tried to score a second date, planning to drag me to the state fair with his entire clan.

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25. Don’t Cross Streams

I went on a blind date. She brought me to a weird party and wanted us to pee on a dude. I was like, "Nah, I'm good. I'll stick to the urinal," and then I bounced.

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26. Too Casual

This guy rocked up to dinner in joggers, nattering on about only dating nurses because he's a slob and they look after him. But wait, it gets worse. He blabbed about his ex, who, after a hard day at work, came round to do his washing. Now, I'm a chef, but he told me he'd "give me a chance" based on my cooking skills.

When we left, there was a street performer pulling a crowd, and we stopped to watch. I sneaked to the back of the spectators and then made a quick exit.

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27. Mute Date

He was all quiet, didn't say much even when I asked questions. Just shot me this stare. Got the nerve to bail after sitting there for like 20 minutes. Good thing we were at a nearby Tim's, made it a breeze to get the heck outta there and get home.

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28. Not In Your Future

She claimed that she could see angels in three different colors. Apparently, during one of her "encounters," the angel was covered in dark scales, with red glowing lights coming out from her skin underneath. The angel came to her in the middle of the night, crawled to her bed, then placed its hand on her shoulder in order to cast an evil spirit out of her room.

If that wasn't creepy enough, she then said that while I was in the bathroom, an angel came to her and informed her of my chilling fate. She said she knew when I was going to die and how it would happen. I told her I'd be right back, saying that I left something in the bathroom. But I left instead, completely creeped out by her. I still wonder what strange stuff she was getting into.

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29. Great Expectations

I beat her to the restaurant and got us a table. When she arrived, she strolled over, we had a handshake and I helped her settle into her chair. Then our server swung by to take our orders. But instead of answering, she shot me a curveball question: "What's your annual salary?" I sorta stuttered out an "Excuse me?" because it caught me off guard.

She bore into me with her stare and repeated, "What's your yearly earnings?" I shot a glance at our server who looked as uncomfortable as I felt, thanked them for their help, then turned to my "date". I apologized and told her I gotta bounce. So, I stood up and exited stage left.

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30. Three Of A Kind

Met up with a girl for lunch. Nice out, so we sat in the open. She was a bit quirky but no major alarm bells... until she dropped a bomb: "Yo, my husbands on his way with our dog. Come say hi". Totally blindsided me, but before I knew it, they were both there. We made small talk, I kinda ignored the dog, cause the whole thing was pretty awkward.

Picked up the tab, made a quick exit, left them to do their thing. The guy seemed cool, he definitely deserved better.

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31. Not A Match

I swiped right on this chick on Tinder - she was a "furry" and I'm not but she's hot and I was down for some fun. We planned to chill at her downtown apartment, which was mind-blowingly fancy.

Then I walked into her living room and found a dude. Her roomie? Nope. A buddy? Nah. This guy was her boyfriend. Suddenly it clicked - she was polyamorous and hadn't mentioned it. Major no-go for me.

I awkwardly sat through her trying to make nice between me and the guy, but he didn't seem to want to chat. Didn't bother me too much - I wasn't too keen on him either. I split after about an hour. Not a great experience, to say the least.

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32. Stay Inside

During lockdown, I had my first online date. This girl couldn't stop talking about how bad outdoor cats are for the environment. Regardless of the convo starter, we always ended up back there—it did my head in.

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33. Replacement Dad

So, I met this chick online. Her profile looked cool, really fun. We agreed to meet up at Denny's. When we got there though, she dropped some bombshells on me. Turned out, she was a decade older than she had told me and was a divorced mom of two.

Seems like she was on the hunt for a new dad for her kids and thought I might be the guy. She even had a specific income in mind that I should be making. After picking up the bill, I politely peaced out. That was my biggest "No way, Jose!" moment in my dating life.

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34. Chivalry Is Gone

I drove us to the restaurant. As I was about to parallel park, he insisted on doing it, stating that women aren't good at it. Great start, buddy. At the meal, he disregarded the female staff. Met a couple of rad surfer guys when I left the ladies' room; they told me my guy was lousy. Lots of warning signs. I laughed it off before heading back.

As we left, the surfers were outside too. I bid them goodbye, and my guy freaked, shouting, "She's with me!" I asked him to wait outside the car so I could unlock it. But nah, I just peeled out, leaving him dumbstruck. The surfers cheered me on, shouting, "Get it, girl!" What a good ending to a downright cringeworthy date.

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35. Not Ready

On a hot summer day, I was heading to pick up a girl for a date in my cooled-down car. Once I got to her place, she hopped in. Not long into the drive, she requested I turn off the A/C. She felt like she was getting sucked in. Strange, but I shrugged it off and did as she asked.

Few more minutes on the road, she took out a water bottle from her bag. Then, out of the blue, she asked if she could brush her teeth in my car. That's when I realized it wasn't gonna work out. I made a U-turn and drove her back home. Without a doubt, probably one of the most bizarre dates I've ever been on.

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36. Merry Christmas Rusty

The first sign something was off was the guy's age. Apparently, he'd lied about it on his dating app...turned out he was the same age as my dad. Despite this, I decided to give it a shot anyway. Huge mistake. When we were chatting before the date, I mentioned I liked F1 racing, and he mentioned going to the Canadian Grand Prix once. To back up his claim, he even brought an old photo album.

Before he showed me the slightly out-of-focus Grand Prix pictures, he went through aged photos of his ex-girlfriends and ex-wives from the '70s. You know the type, curly perms, bright blue eyeshadow, and cheap, tacky lingerie. He also showed me a photo of a beautiful Irish Setter. My exact words were, "Nice dog". He responded by telling me how he'd run over the dog with his truck one Christmas. What a way to celebrate, huh, kids? Dad just crushed poor Rusty. After that, I decided to call it a night.

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37. Don’t Be Stingy

She kicked up a fuss for free food just because they didn't put ketchup on her burger at a restaurant. Imagine, all that drama just for missing ketchup as if it's the apocalypse or something. There was a ketchup bottle on our table!

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38. Your Insecurities Are Showing

She always teased me. Although we're both 26 and in the same stage of our career, she made ageist jokes, calling me old. One day, I'd had enough and told her, "This isn't fun for me anymore, I'm leaving". I paid the bill and left.

She later confessed she was mean because she was covering up her own failures. She said she felt bad about her age. But to me, it sounded like she insulted others when feeling insecure. Nah, not cool.

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39. Too Excited

My first date with this dude from an online dating site was a trip to the Scientology museum in London. I thought, "Hey, that's different and could be a good chat starter, so why not?" Man, was I off! He was super serious about the whole museum thing, reading all the info at each display and grilling the museum guy about how to join Scientology. He seemed way too curious to be just casually interested. Plus, he was seriously sweating. Like, a TROUBLING amount.

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40. Family First

So, I had my first date with this high school guy. Post-dinner, we hit his place for a bonfire. I met his dad and stepmom, then we chilled on his balcony. His folks could totally see us chillin' from their living room.

Outta nowhere, he says, "I told my dad I'd always score that first-date kiss". I couldn't believe how awkward it was. But what came next was even weirder. He pulled me off my chair, and I was sitting awkwardly, half-straddling him, while he tried to make out with me. I nixed that pronto and dialed up a friend for a quick exit. The worst part? His parents were practically next to us. No way were we going to talk after that drama.

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41. Utterly Delicious

My date couldn't keep in his groans in every time I munched on a breadstick at Olive Garden. When I asked, he nonchalantly said that women eating turned him on. I had my sister on standby at a close-by Target just in case, and I sent her an urgent "Get here NOW" message. I just stood up and split.

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42. Won’t You Be My Neighbor

I didn't even realize that it was a date, honestly. A few years back, after moving into a new neighborhood, the dude living two doors down invited me and my kiddos to a bonfire. He had a daughter, around the same age as mine and reassured me it'd be a family-friendly gig. And so, we headed over.

The kids had a blast, running around together. I planted myself next to a woman, thinking, "Nice! A chance to mingle with the locals". It was fun, until she asked how her bro and I hooked up. After clarifying I just lived next door, she squealed, thrilled that her bro had bagged a girlfriend - me! I mean, what?!

Apparently, he'd announced to everyone that I was his new flame. He thought introducing me to the fam at this bonfire was romantic, or something. I almost wondered if I'd walked into a hidden camera show. It got weirder when he cozies up, hand on my shoulder, calling me someone else's name! Everyone's grinning ear to ear, while I'm red-faced, stuttering, "Uh, no. I just met you a few days back… moved here two weeks ago".

I rounded up my kids, made a quick exit, and kept clear of bonfire guy after that. His daughter could chill with my kids, but only in a neighborhood group. Never found out what tall tale he spun to his family about my jet-speed departure.

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43. Momma’s Boy

So, before I hooked up with my hubby, I went out with this guy I found on a dating app. He seemed alright - kind of sweet and ordinary, so we planned to catch up over a coffee in a park. We'd barely started chatting when he drops the bomb about owning a cat. Being an animal lover, I was like, "Aww, what's its name?" Then comes the stunner - he lists not one but fifteen names! Yup. The dude owned fifteen cats with his mom.

Speaking of, he was still living with his mom, and the wheels he was in? Mom's, but he claimed he was keeping it in check. And he hadn't stopped there, he'd already mentioned our date to her and shown her my pic. The most jaw-dropping bit? His mom thought we'd have pretty decent-looking kids together. I was like, "What?" and bolted.

Fast forward a couple of days, and he manages to track me down on social media, even though he didn't even know my last name. He was pinging me non-stop for like, three weeks, asking why I wasn't answering his calls or texts. So, I just blocked him. I thought I was in the clear and got back to my routine... but he still didn't quit. He snooped me out on yet another dating app and started messaging me there!

His messages were downright creepy, to be honest. He kept yakking about how we'd be this awesome couple and how I'd be a super wife. He even went on about how pretty he thought I was, but then suggested I consider going blonde. Like, seriously? Such a weirdo.

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44. Miscommunication

I met this exchange student while playing soccer at college. He was pleasant and we hung out often. Once, he invited me to dinner. At this point, I was recovering from a tough breakup and wasn't ready to date, and I told him so. He said he was okay with just being friends.

The dinner went fine until he decided to lift me without a heads up. I wasn't comfortable and asked him to put me down. His justification was that he'd seen my old Facebook photos, knew I was once a bit heavier, but now I looked good, hence I shouldn't be self-conscious.

Even though this weirded me out, I brushed it off as a cultural gap since he'd been friendly earlier. Later, he invited me to his place to meet his roommates. Thinking it was all platonic, I agreed.

Soon as we got there, he took me to his room, pulled out a headscarf, claimed it belonged to his mom and his future wife would wear it. Then, he placed it on my head. Taken aback, I tried to hand it back but he insisted I keep it. I was feeling very awkward and responded that I couldn't accept such a meaningful gift from him.

Suddenly, he grabbed me, fell back onto his bed still holding me and tried to kiss me. I pushed him away and yelled at him, but he attempted it again. I quickly ran out while he watered me down with insults. The next day he texted me, calling me cold and overreactive.

I blocked him immediately. A few days later, he was outside my workplace when I was finishing, holding a wireless phone charger. Apparently, according to him, I hadn't been texting him because my phone had charging issues.

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45. Child’s Play

About a year and a half ago, I was in my twenties, recently heartbroken and recovering from a four-year relationship. The dude dumped me while considering popping the question, and frankly, that scared me. During my single life, an adorable former colleague asked me out. I'd been solo for three months, and hey, no harm in dating again, right? I was a tad anxious — first date post big-breakup — but he was a nice guy, so I figured why not.

Just when I was keen, he texted, admitting he hated driving and had let his license expire. First red flag, but anyways, I drove an hour to pick him up. He routed me to a mall which left me puzzled, but I went along — maybe it's coffee, hang out, and chill. But the first thing he did was squeal about a sculpture of questionable shape and gave himself a good laugh.

And then, Rainforest Cafe and his fascination for their robotic gorillas. Strange, but it's just a date, right? I wanted a drink for my nerves, he agreed, and I ordered a spiked cranberry. This guy surprises me by ordering from the kids menu and gets a plastic smoothie holder with a cartoon king of the jungle smiling at me — filled with chocolate milk.

He mumbled he wasn't a fan of liquor and was excited about the toy that came with his drink. Adding to the weird, he tried convincing me to fake a birthday so that we could score a free dessert because he loved sparklers. As he reveled in his strange plans, I found myself regretfully teary, discreetly using my cocktail napkin as a tissue. 

Horrific Blind DatesShutterstock

46. Don’t Dare Compare

My first year at college, I connected with a guy on OK Cupid, leading to our first dinner date. He offered to pick me up, but it felt a bit sketchy because he was older. Over dinner, he chatted about his successful post-college start-up. It was impressive, even if he was a bit boastful about it all.

After ordering food, he propositioned a strange game: comparing our wallets. Yep, it was real. He proudly paraded his credit cards, flaunting their sky-high limits. He finished with, "Obviously, you can't foot this bill but don't sweat, I've got you".

I was mad and tried arguing but he wouldn't hear a word. As we left, he wanted me to check out his car, parked closer to the entrance than mine. It was a white van with no windows. He was quite keen for me to jump in the back with him, right there in the parking lot. Thank god I drove myself!

Customers paying waiter at restaurantGetty Images

47. Eat Fresh

I had a date with a dude I met online. He's like, "Dress nice, I'm taking you to dinner". Ends up at Subway and scores a foot-long teriyaki chicken sub. Looks at me, goes like, "I guess you're cool with teriyaki chicken". We munched on the sub in his car. Needless to say, date number two isn't happening.

Co-Worker KarensShutterstock

48. Nay To PDA

So, I planned to meet up with a lady in her 30s at Starbucks. Once there, I found a woman who looked nearer to 50 and was much bigger than she'd made out on her profile. Right away, she's chatting about super private stuff, like my preferred positions. All this in a Starbucks packed with people, including kids.

Normally I'm chill, but this was too much. So, when she reaches for my hand, I said, "Hey, not a fan of PDA". Made up a polite out and left, telling her I wasn't feeling well. Thought that was the end of it, but nope.

She trailed me out, got a bit handsy, tried to grind against me, even went in for a kiss. I firmly reminded her that PDA wasn't my game and after a few tries, she finally let me get in my car for a restless escape. After that, I mentally hung the 'Closed' sign on my dating life for a while.

Weirdest Date FactsShutterstock

49. Beyond Inappropriate

Swiped right on a guy from an app and things seemed cool, so we got a bite and took a stroll around town. Everything was chill until we hit this alley. Dude stopped, looked straight at me and dropped the creepiest line I've ever heard on a date: "You look so hot, I feel like jumping you now".

I thought I heard wrong so I made him repeat, and he just made it worse: "I want to throw you down and jump you now!" I called him out on his twisted statement and split, but he caught up claiming it was all a joke. However, as my train pulled in, he said it AGAIN, blaming me for looking too tempting.

I ditched him then and there, told him to lose my number. Despite my clear message, he blew up my phone all week, griping about me not getting his humor, calling me 'probably a tease anyway'.

Awkward Crush factsShutterstock

50. Red Flags

So this guy was about a decade older than my 19-year-old self. Since I didn't have a set of wheels, he fetched me from my pad. We had dinner and it was kinda weird, but we had scheduled a bowling sesh after, and I was too timid to ditch the plan. Just shrugged it off and went with the flow. But then, things got dodgy when he claimed to lose his way to the bowling alley.

Next thing I knew, we were in the depths of a pitch-dark forest. I was genuinely scared, I was sure that it wasn't just my anxiety upping its game. The guy was super creepy and there was this outright eerie air around him. Luckily, after an unnerving ride, we did end up at the bowling alley.

Playing smart, I excused myself to the washroom, and when I returned, I faked having puked and asked him to drop me home. To my relief, he obliged without any detours this time. Post that, I went MIA on him, but the creep still found my email and hit me with a guilt-trip for ghosting him.

Honestly, I was just relieved to get out of there in one piece. I relocated ASAP since he knew where I hung my hat. From then, I've always made sure to meet my dates directly at the venue, and I stick to Ubers for getting around.

Creepy DatesShutterstock

51. First And Last Date

I went on a date with an amazing woman I met online. We hit it off while chatting for weeks beforehand. The date was awesome—we clicked instantly, had tons in common, and spent the evening at a fancy lounge, laughing, chatting, and feeling a real connection.

Eventually, we started talking about being single parents to daughters the same age. When she showed me a pic of her kid, I did the same. Then things got crazy. She recognized my daughter, even knew her name. I hadn't mentioned her name. Scrambling, she suddenly claimed that our daughters knew each other, despite living far apart. But then she blew the secret: She let slip that she new my ex.

At the time, things were rocky between my ex and me. Between knowing my daughter AND knowing my jerk of an ex? I don't know WHAT she was planning, but it couldn't have been good. I got the heck out of there.

Couple are drinking coffee and looking at cell phone.gpointstudio , Freepik


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