“56 Insane Dating Stories So Bizarre You Won’t Believe They’re Real”
Ever had a date so wildly unexpected you just had to rewrite your dating profile? Picture this: your online bio boldly says, “I don’t care how tall you are,” then along comes a dude who looks like he could star in a kids’ show—complete with a lifted truck, a shy demeanor, and a wickedly high-pitched giggle that sends chills down your spine. Suddenly, the rules of attraction get rewritten in real time—because when your date stands at about 4’5”, you start thinking maybe height—and shyness—really are the ultimate pick-your-poison struggles. Welcome to the land of first-date escapades that make you question reality and, frankly, your judgment. Brace yourself for a rollercoaster of anecdotes so bizarre, so cringe-worthy, and so utterly human, you’ll both laugh and wince along the way. Ready to dive in? LEARN MORE
I had a line in my online dating profile that said “I don’t care how tall you are😆”
I had a date that made me change that.
He had a really nice pictures of him at the gym but when he showed up ISTG he looks like he was about 12. I thought Chris Hansen was going to jump out and arrest me. He drove a lifted truck and was VERY SHY. Had a creepy high pitched giggle. I changed my profile to say “you can be short or you can be shy, pick a struggle!”
He was about 4’5″.
Seriously.
He was in a Maroon 5 cover band, which I did not know before our first date. Instead of driving straight to dinner he surprised me by driving around for an hour so I could listen to him sing along to his own cd. An HOUR.
And as cringey and disappointing they may be, most aren’t scared away. More than half (53%) of men and over two-thirds (68%) of women say they want a romantic relationship.
She bit me. And I mean, she CLEARLY saw it as flirty and playful and I do get that. But she broke the skin. And REFUSED to let go when I said she was hurting me. I finally snapped at her to please stop. She deflated like a balloon, then began that silent “I can’t catch my breath” sobbing. I could feel every eye in the restaurant on us. I paid, apologized, and took her home. She was silent the entire ride, then before she got out told me I was making a mistake by losing her.
Yeah, no.
Met a guy through one of the apps. Made sure he *knew* I was an athiest, no interest in religion at all. He insisted he had no problem with that. Get to the restaurant, sit down, and he hands me a wrapped gift. It was a book about coming to jesus. Shortest first date ever.
Went to to go see a girl I liked that I thought was having a mental health crisis. She said she just wanted to drive around and talk. So we did. We got blue lighted coming out of her apt conplex and refused to pull over. Ended up leading us on a high speed chase in 3 diff counties and we got pit maneuvered by a state trooper
For some people, this lack of predictability and security results in an increased need to find a partner, while for others it can create a hesitancy to make decisions and commitments, Ford explains. Which, as we can see from the stories, can lead to a lot of awkward situations.
I woke up, the guy I was seeing slept over but left before I woke up. So I go to the bathroom and see that he had diarrhea all over the toilet, floor, rugs, bathtub, shower curtains, etc. I was so horrified I went back to my bed – pulled back the cover to see he had [pooped] the bed as well.
So many to chose from but my favorite was the time I went to a guy’s house for the first time and he made me watch 40 min of videos of him driving a plow truck through snowy parking lots (I live in Iowa, this is not impressive, and I don’t think it would be even if we lived somewhere without snow). Then he told me that HE STILL LIVED WITH HIS WIFE AND SHE WAS UPSTAIRS, I told him I was no longer interested in pursuing anything with him. He got super offended and told me I was being unreasonable.
Had a blind date. We met, walked around, asked a few questions and realised. That’s not it.
So we stopped the date and each one was going home. I had quite a long way. Nearly an hour of public transport and two switches.
And I saw her every damn time.
Even at my home station.
I avoided to speak to her and fell extra behind to not make it more awkward.
Welp right in front of my house she waited for me and shouted: What’s the matter?! Stop stalking me.
I went over to this guy’s apartment to smoke and chill. I was young and stupid. Please don’t come for me. I get there and we go to his bedroom and start smoking. I’ve been there for five minutes and someone knocks on his door. He goes out to check who it is. 15 minutes pass. He texts me it’ll just be a bit longer. 25 more minutes pass. He texts me telling me that it’s his ex outside and asks if I can please leave through the window.
Had a date off an app 2nd time so brought his overnight sack. Long flowing gorgeous hair, smart medical researcher. He goes to use my bathroom, why this man come out asking why I don’t have any meds in it? Pain pills I ask, nope he wanted hard stuff to steal. Made sure he didn’t come back but regretted it, he was fine all over AF.
Long story short, found out he was married when his wife texted me like 2 days after we became official. He is no longer married and I have a new bestie now
Has been on a couple of dates, wasn’t going anywhere & I called her to end it. Before I could:
Her: I wanted to talk to you about last night, im really upset you didn’t try to kiss me
Me: I didn’t think you wanted me to
Her: I didn’t, I’m REALLY upset you didn’t try.
Best I can tell, she really was very unhappy about it, it wasn’t an act.
His car was filled with garbage and vomit remnants. It smelled like a hot dumpster. He tried to act like it was no big deal. I did not speak to him again. He started working at my job a few months later
Spent the night at his place, in the morning he wakes me up at 7am “you have to leave, my mother will be over soon to clean up”.
I have so very many but let’s go with…first date. I meet him at the restaurant and he is already several drinks in. He proceeds to get blackout drunk. I loaded his 6’4 280 lb frame into the front seat of my Subaru and somehow found his apartment complex. He could barely get out of the car. He then wet himself in the parking lot. Me being 5’2 180 lb pushed his big old self up 2 flight of stairs and got him into his apartment. This fool asked me if I wanna spend the night! SIR!
Mid-80’s. Older woman at the gym fixed me up with her son. He arrives with a red rose and I was gob-smacked. He was GORGEOUS and sweet. He wants to take me to the latest “video bar” for drinks and dancing (it was the 80’s, y’all!). We hit it off on the ride over and I was really getting exited. We weren’t in the bar 5 minutes when he says “I see someone I know, I’ll be right back”. Next thing I know he is screaming and crying at another man and his wife. Turns out it was his boyfriend.
Lady tells me right out of the gate, “I’m a triple Scorpio. I’m intense. I’m deep. You’d better not cross me! Etc.” She wanted Thai so I took her to a noodle spot. I wore a nice black tshirt (nice fit, no graphics), dark jeans and nice boots, had a nice haircut. She was not dressed up. We ate and talked, I paid the bill; no chemistry. I said bye and gave her a hug. She texted me after-said I didn’t look nice for the date, didn’t take her to a nice enough place & she never wanted to see me again
Was invited to a casual party, just people celebrating life.
I’d only met her a few days previous at a friend’s gathering. He told me she was cool, and a fun person to hang with, that she had asked if I was single. So I said sure.
It was an engagement party turned wedding, and she got all possessive when her friends started asking about me.
I freaked out big time and told her I was leaving, that she should get a ride home from one of her friends.
I literally had to block her everywhere.
Met this guy, hit it off, exchanged numbers. Asked if I wanted to go to a movie, sure why not? We had a bit of time to waste, so we walked around a mall that was right next to the theater. This guy took me to a Kay’s Jeweler and tried to get me to try on ENGAGEMENT RINGS. On our first date.
I went on a date with a guy who I thought arrived in an uber. I was sitting down in the restaurant so I didn’t see his driver or see him arrive. Apparently it was actually his girlfriend who drove him! He told her it was for a business meeting. I found out… eventually
Not my story but my friends… she met a guy online. They go out for a coffee date. He’s attractive, articulate, well dressed, funny. They really hit it off but she runs a background check anyway. So turns out he’s been arrested for bigamy more than once. There are news articles about him. We found his Facebook page he’s got loads of friends, but all the female ones have multiples of the same first name… like 20 Amy’s, 15 Jessica’s, 10 Leslie’s…and so on. Yeah she went ahead and blocked him
I’d met this dude in passing at church and said yes to a late afternoon coffee date. As we finished our coffee, he asks if I’d be down for dinner. Yknow what, sure. Guy brought me to his sisters’ joint birthday party (1 year and 3 days apart) at his mom’s. It was 2-3 weeks after their preacher dad passed away. There was a card from dad to one of the girls- they didn’t know which. Much sadness and tears. Then he like ANGRILY insisted we watch Hard Candy. It was supremely, INSANELY awkward.
I went on a coffee date with a guy. He was a reeeeeaaal dim bulb. He kept asking me what the words I was using meant. I have a decent vocabulary but I was just using like, normal English words like “meander” and “mortified.” Then when I finally got away, my car had been towed. Had to get a ride from him to the tow lot to pick up my car so it ended up costing me almost $200 to have a terrible night and be a human dictionary.
Dating app guy. We meet. Cliche- he looks nothing like his photos, is significantly older, and 5’6” maybe- not the 6’1” he claimed to be (idc about height. I do care about multiple lies).
He finds out I’m working in a vet hospital and then shows me dozens of photos of his black lab, immediately followed by asking me about every single condition he thought the dog might have. I suggested he bring her to the clinic with his concerns. He adamantly refuses. “She’s just a dog.”
I walked out.
We finally added each other on Facebook. We had like 40 mutual friends, but I didn’t look through all of them. He asks me how I know this one girl he saw was a mutual. I ask why he’s asking. He said “oh I hooked up with her at a party and never got around to unfriended her”.
IT WAS MY LITTLE SISTER
Not my absolute worst date; it was the late 70s and I was about 20. A guy I liked came over to my apartment and after a while we started making out. I reached over to pull him a little bit closer and it was hard as a rock, and no, not that, it was his leg. His leg was hard as a rock.! I must have looked really puzzled being slightly inebriated and he told me he had a wooden leg. I have to admit to being extremely immature, but an actual wooden leg was just too much for me.
I went on a night date with a guy who showed up to an Italian restaurant wearing white yoga pants. White. Yoga. Pants. At night. To a packed restaurant. And of course — he hadn’t made a reservation. The place was completely full, so he actually begged the waiter to let us keep a table for 30 minutes before the next reservation arrived. That was red flag number one, but unfortunately I decided to be kind instead of smart. We sit down. A few minutes into small talk, he starts talking about his mom
Then… dramatic pause. Full silence. And suddenly he starts sobbing. Not tearing up. Full-on, shoulders-shaking,not breathing crying. I’m thinking, oh my God, this poor man just lost his mother. So I gently ask if it was recent. He says, “It was about 15 years ago.” Fifteen.Thankfully, the waiter comes to reclaim the table. But he is not moving. The waiter asks once. Twice. Three times. Finally I basically order him to get up.
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