The dating landscape is a battlefield. You’d think with dating apps and online communication people would be able to weed out incompatible partners more easily before they arrive on their first date. However, if these stories are any indication, that is certainly not the case.
1. Might Be Too Early For That Conversation
Gotcha, he's got two of his exes who've put restraining orders on him. Plus, he asked to move in with me on date one!
2. Looks Can Be Deceiving
So basically, this guy's got a fancy law degree from a top-tier university. But delve a little deeper, and you'll find out the twisted truth about him. He's got six kids from five different women. One of his exes couldn't bear him any longer, so she took the kids and fled to Germany. And that's not even the wildest part. He's got a baby who's just six months old and he's stuck crashing on his ex-girlfriend's couch.
3. Oops, Did I Say That?
Before our first date, he said he didn't have any kids. But on the drive home, he griped about his ex messing up his car settings. That's when it hit me—he's a dad.
I was fresh out of high school and kids were the last thing on my mind. His disrespectful attitude didn't help either, so learning about his child was my cue to exit.
Yet, he wouldn't stop ringing my phone or blowing up my inboxes. I blocked his number, but he kept popping up on social media trying for round two. He thought he could lure me in with his big paycheck, but I wasn't biting.
4. The Creepy Hairstylist
My date wouldn't stop hassling me about braiding my hair, right out of the blue! I thought it was odd but hey, not a total dealbreaker. But he wouldn't quit! The first time he popped the question was when we were chatting and walking through the park. He chimes in, "Can I braid your hair, please"? I chuckle, give a polite no, and get back to my story. But it didn't end there.
He keeps cutting me off with this hair-braiding biz. I question his motive and all he says is, "I just like braiding it," while consistently trying to grab my hair. I had to fend his hands off a couple of times. When that didn't put him off, I decided it was home time.
Creep alert!
5. A Cheater With Poor Road Safety Behaviors
So, the girl I met was actually married. We bumped into each other at a pub and then hung out. Grabbed food, caught a movie, and she crashed at mine. In the morning, she's like "Hmm, think my husband noticed that I didn't show"?
Next, she needs a lift to her job, and I end up with a ticket 'cause she skipped buckling up.
6. A Crypto-Pusher
He blew a ton of cash on crypto and NFTs. Yet, he was still trying to persuade me to invest my own bucks in it.
7. This One’s On… My Mom
This all happened after our second date, and I couldn't help but be impressed when he took us out for sushi. You know, the friend who introduced us came along too. I was only 18 and he was 27. Let's just say, not many 18-year-olds have the means to lavish sushi on others.
But, here's the kicker. Later on, he revealed that he'd footed the bill with his mom's credit card. He was jobless, on the path to recovery from addiction, and he'd been living off his mom's credit cards.
Needless to say, that was a deal-breaker for me.
8. Court Fees and Chases
He wanted me to cover his court costs—that was a buzzkill. I decided it was time to bounce but when I tried to, his reaction was bizarre. He threatened to spill to everyone in the restaurant that I was cheating on him. So, to avoid any public humiliation, I played along.
I made some lame excuse about needing to use the bathroom, which was my chance to bolt. As I was leaving, I spotted him through the window, so I picked up my pace a bit. When I looked back, there he was, right on my tail.
9. Probably Should Avoid The Word “Duty”
He excitedly said he was pumped for us to have kids and that he already had names in mind. I reminded him it was just our first date and I wasn't all-in about the kids thing yet, plus it was kinda weird. He was all like, having kids is a must for women and would bring me happiness.
Needless to say, I didn't sign up for a second outing.
10. Drove Her To Another Guy… Literally
So, she had another date lined up right after ours, with her steady guy! Not even the following night, but literally five minutes later. I had to take her straight to her next rendezvous. Seriously, why go out with me if you're taken!?
I didn't even attempt to make a move, yet she still smacked a fat kiss on me to say bye.
11. This Date Included Toenails
My date confessed he doesn't trim his toenails. He lets them grow intentionally, claiming they're his leg scratchers.
He said, "Saves me from bending all the time".
When I saw those claws, guys, I bolted. Boy, did I run!
12. Can I Eat My Pancakes First?
So, this guy I met who seemed totally chill, we decided to meet up for a breakfast date. Just before our food came, out of nowhere, he blurted out something that made my blood run cold. He told me I was beautiful but that I would look even better with his collar on and his baby in my stomach. Totally off guard, not even close to whatever we were chatting about then.
I got right out of there, said the breakfast wasn't happening, and bolted before he could add more to the awkward. Blocked him the second I got home.
13. He Did Magically Make A Second Date Appear
My date totally bombed at magic. He had all the cards, but none of the tricks. I felt kinda bad and gave him another shot with a second date, but that was all.
14. Bossy Pants
He kept bossing me around. It felt okay at first, but when it happened again and again, I thought, nah, I'm not up for this anymore.
15. The (Married) Date Next Door
I hooked up with this cool person on a dating site while I was in the middle of a move. We texted on and off during the week, he mentioned living near this lesser-known park. Wouldn't you know it, my new place is just a short walk from that same park.
Guess who my new neighbor is? Yep, that guy from the dating site. But there was a disturbing twist. He's been married for over two decades and has three kids and a dog. So, I do my best to keep our interactions to a minimum.
16. (Shouldn’t Be) Looking For Love
I reckon she was actually in love with her bestie but just didn't know it. She used to say she lived in this one-room place with her childhood mate and her baby—she liked to call her "wifey". They were close as anything, always putting each other first no matter what. The duo seemed to bounce from one pad to another, getting booted out a few times.
One time, we were out on a date and she had to split early. Apparently, their landlord was putting the heat on 'em, threatening to toss them out. That was the last we seriously chatted. If you ask me, she probably shouldn't be dating anyone else—she's already in deep with someone, only she doesn't realize it.
17. The Unnecessary Lie
They lied about their age to get me to go on a date. I wouldn't have minded the age gap, but the lying didn't sit right with me.
18. Height Doesn’t Matter
I once went out with a guy who fibbed about his height, just a few inches. Honestly, his real height wasn't an issue, but if he can blurt out a lie about something so visible right off the top, what else would he lie about?
Public Domain Pictures
19. The Online Person Vs. The Real-Life Person
The story goes: So, I had these buddies who told me that this chick I'd been DM'ing on Facebook was into me. Our chats were always fun and engaging, and she seemed totally invested in our convos. I thought, "Sweet, maybe I'll ask her out to lunch". But before I could, I find out she already knows I'm kinda smitten, and she's all hyped up to ask me out instead.
When I met up with her, I was surprised. She was dressed in a huge jacket and a sour face—in April, mind you—she met me for our date. We headed to get pizza. But the entire time she was glued to her phone, texting away, and droning on about her cats—like, the whole freaking time. No joke.
When the pizza arrives, she didn't once look up from her phone or stop her cat monologue to even take a bite. Tried as I might to be a polite sport and veer the talk to something else, it was clear she wanted me as her captive audience to her infinite cat tales.
By the time we got back home, I was so over the whole ordeal. I bade her goodnight, wished her well with her furballs, and told her to hit me up if she felt like it. Spoiler: she never did. Instead, I hear from our friends that she's been accusing me of ogling her all through the date. To this day, that accusation baffles me even 13 years later. Absolute waste of time, zero out of 10.
20. Cool Story, Bro
This guy was broke, couldn't get home, and asked to crash at my place. No way, dude.
21. You Never Want To Know What’s In A Woman’s Purse
The first date went well, but the second date? Not so much.
I found out she had morphine in her bag, swiped from her workplace, a hospital in the Bronx. She said it was just in case she had a bad hangover from our date. Oh, and she watched a stabbing victim die that day as part of her job, but she she was super nonchalant about it.
But the worst was yet to come. At the end of the date she says something like, "If you'd been meaner to me, I might've hooked up with you". So, if the theft and the cool-as-a-cucumber attitude about a dying patient wasn't enough, that last bit really sealed the deal. No thanks.
22. Moving WAY Too Fast
He asked me to call his girlfriend to tell her we would be together now.
23. Interesting First Greeting
So, this guy walked into the bar. He was the same guy I'd been chatting with on the dating app, you know? Instead of a normal 'hi' like a handshake or hug, he did something I'll never forget. He randomly licked my face. No kidding. And then? He wouldn't shut up about wanting to hook up. I was so freaked out that I bolted.
24. Fashion Choices And Forward Requests
She rolled up dressed like she was just popping out to the gas station to grab some milk, and she was super late. First thing she did was ask if we should get a room. Uh, no.
25. Who Am I?
She told me she was a Christian life coach. She then asked me what my personality type was and proceeded to try to tell me about who I was and why.
26. Excellent Table Manners
He accidentally knocked over his drink on the menu, then casually sucked it up.
27. One Word: Negging
It's crazy how many dudes still believe playing the negging game will help them flirt better. Despite what WikiHow might tell you, tossing out insults at a gal doesn't make her want to win your approval. It just shows her you're a jerk.
28. Definitely Not A Foodie
He only liked a few foods. Although he was cool, I couldn't picture another date because I love eating out. On our first date, we already maxed out the only local joint where he could stand any of the food.
29. Money Talks
They wanted to know my income and what's in my savings.
30. Is This A Date Or A Pitch?
She was really into multi-level marketing. She was all about me dropping money into this tech company which was supposed to bring out internet, cable, and cellular services. But, she also told me to check out their top-notch health supplements and skincare stuff.
31. Too Fast And Furious
They were driving like crazy and super fast when I was in the car, probably trying to impress me. I didn't agree for another date but we kept talking. They ended up wrecking their car the following week.
32. Not Ready To Move On
They couldn't stop chatting about their ex, so it was obvious they hadn't moved on from their old romance.
33. When Complimenting Becomes Othering
If they keep labeling me "exotic" or can't stop complimenting my skin tone, it gets annoying. It's even more frustrating when they mention that they've never dated anyone from my ethnicity.
And then, if they've only ever dated women who look like me from a specific ethnicity, it feels like I'm being patronized.
34. She Thought It Was Complicated, But He Didn’t
So, this happened back in college. Met this girl at a friend's birthday bash—she was friend of a friend's friend. From the get-go, there were signs of trouble brewing, like her lying about being a sophomore when she was really a freshman. But, eh, no biggie.
Our first date was dinner, followed by ice cream, and she invited me over to her dorm for a movie. With her roommate gone for the night, we ended up hooking up. She was a wild mix of fun and hot—an irresistible combo.
Fast forward to two days later, she's at my place for dinner with me, my roommate, and his girl. After dinner, I chauffeured her back because she had a test the next day. As I went to see her to her room, she stopped me outside her building and revealed the truth. She has a boyfriend who lived eight hours away. Her roommate was in the know, so I couldn't walk her up to her room.
Yeah, that was the line. Took it cool, told her to hit me up if things didn't work out with her guy. She tried getting back in touch the next weekend. Checked if she was still with her boyfriend, she gave me this "Yes...no...it's complicated" stuff, so I hung up. That was it, never saw her again after that.
35. Table Manners
If you chomp loudly or eat with your mouth wide open, that's it. I doubt I would last till the end of the meal.
36. A Difference of Worldviews
So, I went on a date and let the guy pick me up. We hit the driving range, had dinner, and had tons in common. I was having a great time and was pretty excited about him.
I liked it so much I suggested we grab dessert. On the way, though, things went sideways. Suddenly, he's going on about women being destined to be with one man, while guys are meant to be with lots of women. He insisted he was different, but still, "304s" were exceptions to the rule. Then he started talking about women who dress provocatively (all while I’m wearing a skirt).
Once I got over my surprise, I spoke up. Realizing this wasn't going anywhere, I tried to steer the conversation to something else. But he wouldn't drop it.
To top it all, he kept going for an hour, rambling about men's and women's "biology" and chucking in some religious stuff I can't recall. In hindsight, I should've hopped in an Uber, but in the moment, he was my lift, so I just nodded and smiled.
The next day, I texted to say our views were too different and it wasn't going to work. He tried to persuade me that we had fun and what did worldviews matter? "We could’ve been happy". Yeah, I'll pass, thanks.
37. Smoking and SoundCloud
He parked his ride in a lot that shut their gates after hours, so he got trapped. He needed it to get to work next day and was a solid hour drive from his place, so I drove him back.
He wondered if he could light up in my car. Not really my thing, but he had a tough day and I felt for him, so I agreed. Big mistake. He then spent an hour chain-smoking on two packs. To top it off, he had the nerve to ask to jam his SoundCloud raps in my ride. After an hour of that, and my car’s inside forever damaged, we were done.
38. Fight, Fight, Fight
She enjoyed seeing her dates get into fights. She'd lure some random guy with flirty eyes, expecting me to fight when he chatted her up. Nah, she can maybe hitch a ride home with him instead.
YAKOBCHUK VIACHESLAV ,Shutterstock
39. Should’ve Swiped Left, Not Far-Right
So, I went on a date with this really hot 25-year-old chick I matched with on Tinder. Probably should've seen the red flags sooner but, you know, she was seriously hot. After only like 10 minutes into the date, I could tell she was into all that astrology stuff.
She finished school at high school level, had a kid, and an ex-hubby who apparently needed a restraining order against him. Also, she had a ton of views that skewed extreme. I booked it right after we finished eating. I texted her, plain and simple, saying that we were too different and I wasn't interested in date number two.
She clapped back, calling me ugly and cocky before blocking me. Huh, go figure. But the ordeal wasn't over yet. Few weeks later, funny enough, she adds me on Instagram. It kinda seemed like she just wanted me to see her post that she's back with her "love of her life"—her ex-husband. What a world, huh?
40. Too Close For Comfort
This might not sound like a solid reason, but back then, it kinda was. She lived in the same apartment as my ex, the one I tried so hard to forget about for two years, therapy sessions and all. She was great, really, but each time I had to drive to her place, the feels just poured in. Too much, man.
41. Interesting Eating Habits
We met at a restaurant. Everything went nicely, but when we were ordering, he insisted I go first...and then declined to order at the same time. Then he watched me eat, and he ordered his food when I was about half-finished. I got up from that table so fast.
42. Should’ve Listened To The Warning
We had a great start to the first date. We’d been chatting online for quite some time, and then we met at a mutual local pub, and we really enjoyed each other’s company after the nerves wore off.
He invited me back to his place, with the warning that he hadn’t tidied up. I’m tidy, but not even remotely picky about a bit of a messy house. I had no idea what I was walking into.
Yeah, no. Not only was every inch of the kitchen counters covered in bottles, but it looked like I walked into a place 15 years after a zombie apocalypse. The layer of dust on every item was shocking. He had some really nice belongings, but all of them were just rotting under the mess.
I actually felt really bad, and I asked if he was okay and had considered getting professional help. His answer was, “Nope, this is how I live”.
I politely excused myself.
43. There Was No Need To Lie
She told me she didn't have kids. I said I was cool with it if she did, but she stuck to her story. Turns out, she's got a 5-year-old. We're both pushing 50 and I wouldn't mind her having a kid. It's her lying that's the problem.
44. High Expectations
Guess what? She assumed I’d be a chauffeur for her kids—whom I hadn't even met—taking them to school and back. On top of that, she expected me to drive her to the hospital for an unplanned surgery, babysit her kids at my place overnight, and then play housekeeper/nanny while she recovers.
And this weird expectation came up after just ONE DATE! No surprise, a second date was off the table. She didn't get why I backed off, saying, "you're my boyfriend now, and that's what boyfriends do".
45. A Hot Mess
I went out with this girl who seemed normal...but on the date, she let her true colors shine. She was kinda all over the place, getting her food in her hair, everywhere really. Constantly on her phone, too. Heck, she even jabbed herself in the face with her fork—wasn't paying much attention, I guess. Haven't seen her since.
46. Sometimes It’s NOT Mansplaining
I had a first date in college. I have a truck and I live in the city, so parking is a squeeze—this one especially. I warned her, "Be careful opening the door, we're crammed in here". Her reaction was brutal.She shot back, "Are you really telling me how to open my door"?
Well, she wasn't really listening and, sure enough, smacked the door right into the car next to us.
47. One-Way Conversation
They kept cutting me off, especially when I was answering their questions. It seems like they're not really paying attention to what I'm saying.
48. A Different Type of “Scoring”
I've got this friend, right? She's only 23, still asks every dude she dates about their credit score to see if they're good with money. Funny thing is, she can't even pump her own gas.
Pakpanat, Shutterstock
49. Downers
They put themselves down to the point where everything ties negatively back to them. Seriously, everything. When we talk, it's even clearer. You'll spot the constant sad expressions, catch them calling themselves "stupid," and saying they don't deserve the good things in their life.
50. Trying Too Hard
I really can't stand folks who think they know everything. Like, I had lunch with a dude who insisted on calling table salt "sodium chloride". He used the bread to give me a whole lecture on complex carbs, some of which was just wrong, and their link to evolution. I felt like he was just trying to prove something.
51. When You Have To Ask If They Know Your Name
So, picture this—I once went on this blind date, right? And oh boy, she only ever talked about herself.
I kid you not, we sat there for like 2 hours and I swear I knew everything about this chick. All about her pet cats, even their favorite movies. Crazy, huh?
Not once did she ask me anything. Just bounced from one thing to the next, just like that.
As we were wrapping up, she's like "Hey, we should exchange numbers"...and it just slipped out. I asked her, "Do you even know my name"? She didn't have a clue. Ended up just paying for my food and ducking out.
52. Clingy Poets
I've got a total dealbreaker for you—making me read your lousy poems. It's happened more than once, would you believe it?
Now don't get me wrong, I kind of enjoy poetry. But on a first date, there's a massive gap between "Hey, ever read this poem? What do you reckon about it"? and "Check out my entire collection, read it all, and hit me with your thoughts".
The first time this happened, I was just 18. We met through buddies of ours. The poetry wasn't actually the worst, it wasn't emo level cringe or anything. The problem was—he ended up spamming me with poems all about me, after meeting just once! Even started calling me his muse, and turned into a total stalker. Big nope from me.
A few years on, it happened again. This guy's poetry was pretty terrible, but I didn't wanna be rude about it. We kept chatting, said our goodbyes in a friendly way, and that was that.
But then, he went from being all nice like, "Had a great time, give me a ring," to "You're probably busy, but do get back," to full on bitter mode, "You're obviously ignoring me, so let's call it quits," within a three-hour texting nightmare. I was stuck at work, didn't even check my phone until lunch!
53. The Job Application Date
One time, I was set for a blind date with a girl. We got each other's emails, chatted a bit, and planned our first meet-up.
On the day, she sent me an email in the morning with an attachment. When I opened it, I was stunned. It was a survey with around 25-30 questions. She asked if I could fill it out before our date. After a quick skim through, I replied, suggesting maybe we should not meet.
I can't say much about her traits, but that was a mood-killer.
54. Opinionless
I went on a date with a girl who appeared pretty indifferent about everything. Honestly, it felt like she didn't have any thoughts of her own. Here's how our chats would go:
Me: "What are you studying"?
Her: "History".
Me: "Any specific era you're into"?
Her: "Not really, just studying it because my folks thought I'd like it".
Me: "Got any career plans after you graduate"?
Her: "My parents think I'd be a good teacher, so I might consider that".
Every single time I tried to find out about her likes, hobbies, or views, she'd always talk as if everything was someone else's idea. And, honestly, it felt like it always was.
55. Their Choice Of Me
If someone wants to date me, that's where they mess up. It really shows they're not making the best choices.
56. When Jerry Springer Is Involved, It’s Probably Bad
So, I once had dinner with this really good-looking guy I met at my apartment complex's pool.
He mentioned his dad was a minister and showed me photos of his church—it was massive and stunning with a wood-paneled interior and high ceilings.
Even though he didn't say anything about his religious beliefs, he made some pretty racist comments throughout our date. I ended the night as smoothly as I could and never saw him again.
Fast forward a few years, these shows like Jerry Springer and Geraldo were all the rage. That's when I found out the truth about the guy I'd been on a date with. During an episode, they interviewed this nutty prejudiced group called the Christian Identity Movement. Surprise, surprise—his dad was kind of a big deal in the group. The church he'd shown me even popped up on Jerry Springer.
It was a big surprise, realizing something can look so pure and gorgeous on the outside but be rotten to the core.
57. Twitter Never Helps
I thought he was a nice guy...but then I stumbled upon his Twitter. Turns out, dude is full-on posting about trashing women and his love for soccer. Caught a tweet where he's dissing me over some opinion I had about an artist. Thought I was dumb, didn't he? Needless to say, I clicked off and dropped him like a hot potato.
58. He Thought He Had It All Figured Out
I met this guy online and after chatting for about a week, he asked me out for sushi. Our text convos had been pretty cool, so I felt good about meeting up.
He picked me up and on the ride we hit it off...or so I thought.
At the sushi joint, he started off by ordering a ton of sushi. I mean, about $100 worth. I kept it light with a roll and some sides, total around $30. But then, things went south...
He spent most of his time texting and taking pics of the food to post online, completely ignoring me. Every single sushi roll...gone. Yep.
It dawned on me what was happening.
The waiter brought the bill while he was still busy with his phone. He didn't even acknowledge the bill or the waiter. I gave the waiter a look, then glanced at my digitally consumed date who was still glued to his phone.
I had the waiter split our bills, 'cause clearly my 'date' was too engaged with his phone to notice the bill. The waiter brought back separate bills, and the expression on my date's face when he was handed a bill for $100 was worth a snapshot.
I paid my bill, gave the waiter a big tip and waited for his excuse. And boy, did he have one: "Oh no, I forgot my wallet! Can you cover me"?
What did I do? I pulled a him on him. I got on my phone, left him at the table and went out the door.
I had already called an Uber, 'cause remember, he was my ride there.
Oh, and don't worry, the waiter got a big tip. I tipped him the same as my bill. I mean, it wasn't his fault my date was an epic fail.
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Sources: Reddit,
