Ever been on an awkward date before? Maybe it seemed like there wasn’t a spark, or the romantic comedy y'all both watched was more problematic than funny. Well it probably wasn’t as horrendous as these dates. These stories feature some of the most insane and awful outcomes for people that really just wanted a peaceful, romantic outing. Single people, enjoy the feeling of avoiding these wild events. Already have a partner? Then hopefully they aren't one of the people featured here. This content has been edited for clarity.
“After A Murder, Everything Else Just Seems Lame”
“I asked a girl out in late spring, so we decided to walk around outside. It was nice out and she went to a different school than I did, so she showed me around campus for a while. We decided to grab a bite to eat at a place in the nearby bar district and sat outside. Halfway into the meal, a hobo wanders down the street playing a harmonica and just rocking out. We barely even noticed him because things were going pretty smoothly. We had just discovered that we enjoyed the same kind of music.
All of a sudden, we hear a lot of shouting and swear words and look over to see that another homeless man had appeared on the scene, angry at the other homeless guy over who actually owned that particular spot. It got pretty heated. We tried to ignore it, but it was slightly impossible as they were about 10 feet away from us.
All of a sudden, the second homeless guy pulls a knife and stabs the first guy in the neck. He died really quickly and blood was EVERYWHERE.
We were questioned by the police, had to make statements and everything. Basically ruined the evening and I got one more date out of it where we struggled to make conversation. After a murder, everything else just seems lame.”
The Worst Time To Run Into His Mom
“My worst date was a 12 hour marathon date that included a trip to the hospital, questioning by police, and ended with her crying. It was followed up by a call from her lawyer 6 months later asking if I would be willing to defend her in court.
She was driving and I was in the passenger seat. She was looking at me instead of the road, like they do in movies when they drive.
Me: ‘WATCH OUT! THERE IS SOMEONE IN THE ROAD!’
My Date: ‘Haha, you are so funny.’
Me: ‘STOP THE CAR THERE IS SOMEONE IN THE ROAD!’
My Date: ‘OH NO!’
She slammed on the brakes. We hit a woman who goes flying across the hood of the car and lands on the side of the road. We get out and go check on her and she is not moving.
My Date: ‘Oh God, she is dead!’
About this time a crowd starts forming, police are called, a bunch of people are standing over the woman when she starts to move and say something. She begins to mumble what sounds like the name of the woman I am with.
That can’t be what she said. I look over at my date and she has a dumbfounded look on her face.
The woman then clearly says the name of my date. The person she just hit with a car is now pointing at her and saying her name. It is like something from a teen horror movie.
My Date: ‘Oh no I know her. She is my ex-boyfriend’s mom.’
You just ran over your ex’s mom while on a date with another guy? At this point I am wondering what she will do to my mother after we break up.
We go inside and call her mother to pick her up. After talking to the police, her mother asks me to drive her van and she would drive the daughter’s car home with her. I then find myself driving a van of a woman I have never met with her two children in it.”
Well That’s One Way To Reject Someone
“I was out dancing and noticed a girl not being all too subtle about her interest. Eventually my friends even picked up on the vibe and keep pestering me about approaching her. Having just gotten out of a seriously long-term relationship, I wanted to play the cool card and strung it out so I wouldn’t have that air of rebound desperation about me. When I did go over and introduce myself, the woman in question give me a quick look over, stopped at my shoes, and said, ‘Oh, wrong pay scale, forget about it,’ and walked away. It was a great way to get back into the dating scene.”
The Trail Of Blood Seems To Be Getting Thicker, And I’m Getting More Freaked Out.
“It was grade 11 and I had just moved to a new town. I quickly became attracted to this one girl. We got paired up to be partners in our Food and Fabrics class, and I totally pulled out all the stops. I was doing whatever it took to get a date with this girl. In the class, there were a couple projects where you would have to sew a pillow case, or a pair of pajamas, etc. My family didn’t have a sewing machine, so we would do the projects at her house. Upon these visits, I began to question how badly I wanted this girl. She lived in what appeared to be a wood cabin, and her father seemed legitimately insane. The walls were lined with animal skulls, the guy was a hardcore hunter. He had bear-skin rugs, and antlers all over the place. He would always walk around with his shirt off, drinking a Budweiser and carrying a weapon. He never spoke a word to me.
By this time I was starting to gain some friends at the school, and one of the guys I met (Neil) noticed that I’d taken a liking to her. He then asked me if I’d heard about her parents. He then proceeded to tell me, that her dad killed her mom and got away with it. Her body was found in the middle of town, pumped with a couple of rounds. He got off on the charges from lack of proof, and his daughter had to live with him because he was her last living relative.
The story made no sense, and I wasn’t about to believe it. But it definitely kinda rattled me. But there was no way that I was going to bring it up to her.
A little time passes, and I ask her out. I go to her place to pick her up, and she’s gorgeous. Her dad makes a comment about, ‘You know what’ll happen to you if you touch her,’ and suddenly the story is the only thing I can think about. We went skating, then to a movie, but I was terrified the whole time. I just couldn’t get the thought out of my head, that her Dad was going to kill me when we got back to her place.
So after a sub-par date, I start the long drive back to her place. We get to the end of her long driveway, and she gets me to park and turn off the lights. She wants a kiss. At this point, I forget her Dad. I lean over, and put some moves on. We stop, and I turn the lights back on. There’s blood in the snow at the end of the driveway. I wanted to say something, but didn’t want to sound scared. Her dad was a hunter, right? I’m sure there’s a logical explanation.
I put the car in drive, and start the winding drive down her driveway. The trail of blood seems to be getting thicker, and I’m getting more freaked out. She still says nothing, as she’s fixing her hair in her mirror. I keep driving. More blood. I turn the last corner of her driveway, and see my headlights shift from the trees to her father. Standing in the middle of the driveway. Covered in blood. Blood all around him with a huge knife in his hand. And there was what appeared to be a bare human body lying at his feet.
I start hyperventilating. Suddenly, I’m crying, and don’t know why. I pee my pants. Her dad takes me to the hospital. Turns out, I have had mild-asthma for my entire life, and had a panic attack. The dad found a bear at the end of the driveway, shot it, took it down the driveway, and skinned it (or, at least the part I saw) before we got back.
Anyways, that was a little over 3 years ago, and I’m still with the girl. Her dad calls me a scaredy cat all the time, except we’ve gone on hunting trips together, and I’m pretty sure he’s a fan. Neil was just a jealous ex trying to scare me off.”
Talk About Phoning It In
“I recently took a girl out and she spent all night on her phone. She was on the phone when I picked her up and got off right before we got out at the restaurant. Then right when we’re about to walk into the restaurant, she takes a call from someone else and talks for about 15 minutes while I’m just standing off to the side waiting. At dinner, she was having about 5 different texting conversations and I had to repeat everything I said because she was constantly looking down at her phone texting.
On top of that, she didn’t eat anything she ordered and drank a ton. By this time, I was way over this date. Of course, she took another call as soon as we got in the car and she was still talking when I dropped her off. I think she was expecting me to walk her to her door, but I just drove off without saying anything.
All together, we may have had three minutes worth of conversation in the hour and a half that the date lasted. She texted me a couple of weeks later asking if I wanted to take her out again. No thanks.”
Your Son Has My Quarter And I Want It Back!
“In high school, I took this girl out to dinner and a movie as a first date. We finish up the movie, and I am driving her home when she says to take a turn here. Turns out, she had decided that it’d be prudent for me to meet her grandparents. This is fine enough with me, as I have an easy time mingling with the golden oldies, but it is about 10 minutes before her curfew when we arrive at her grandparents’ house.
Before we even walk in, I tell her to call her parents and let them know. She puts up a fuss and says they won’t care and to not worry. Time goes by, and we end up at her grandparents for an uncomfortable 30-45 minutes, all the while I am saying that it is past her curfew and her parents don’t know we are there.
We make the 15 minute drive back to her house and it is COMPLETELY UNCOMFORTABLE. The mother rushes her to the next room and mumbled yelling occurs. I’m sitting at a table when the father comes into the house and gives me a death look and yells some more. This is just a bit much for me, but I handle it alright and go home.
As soon as I walk in (within my own curfew) my mom starts yelling, ‘WHERE HAVE YOU BEEN!’ and I’m wondering what is going on. Well it turns out the girl’s father drove to my house and started banging on the door yelling at the top of his lungs that I have his daughter and he wants her back. My mom doesn’t know who this man is, and in the panic from beyond the locked door, she incorrectly hears, ‘YOUR SON HAS GOT MY QUARTER! YOUR SON HAS MY QUARTER AND I WANT IT BACK!’.
My mom freaks out thinking there is a psycho at the door and gets her forty-five, and all the time, my mom is yelling back through the door that, ‘IF MY SON HAS YOUR QUARTER, HE WILL GIVE IT BACK TO YOU TOMORROW!’ to try to appease him. The girl’s dad eventually leaves, and I finally convince my mom that the family is crazy and we have a good laugh about it later. However, this has to be the WORST DATE EVER!
He Did Nazi This Coming
“We were both about 19, and this interesting Greek girl liked me. We’d been talking for a few weeks, and she’d just broken up with her boyfriend, so she asked if I wanted to come over to her house at about midnight.
So I sneak in through her back bedroom window, and this girl has pulled out all the stops. There are candles and rose petals everywhere. This was going to be a good night.
Before things go down, she decides to show me a little about herself, so she’s showing me things in the room. It’s all traditional girl stuff, but then suddenly she pulls out a knife with a swastika on it.
‘Interesting,’ I think to myself. This was a bit of a head scratcher.
Unfortunately I seemed a bit too interested in this, because she then opened her closet and the whole thing is full of Nazi memorabilia. I mean like old war uniforms, tons of knives, whatever she could get her hands on, apparently. She was seriously into this stuff.
At this point, everything in my body is screaming get out, except for what’s in my pants. So guess who won? That’s right, I was 19. So she takes her clothes off and jumps my bones, and I immediately notice that I’m starting to feel kind of weird. The bed starts making noise so we go to the floor. As soon as we get to the floor, I start getting nauseous. I tried to feel better, so I ask her to blow out the candles. I think this is the problem, but it didn’t help. I tell her maybe it’s the rose petals, so she gets rid of those. At this point, I just kept feeling bad, and on the verge of vomiting.
So I made a break for it, just jumping out the back window and leaving. The whole drive home, I’m on the verge of vomiting in my mouth. I get home, barf all night, and end up with food poisoning for the next 3 days.
I never dated Nazi girl again. She stalked me for a while after that. Occasionally she’d past my house, which was in a dead end neighborhood on a court, 25 minutes from where she lived.”
Love Not Actually
“A friend of a friend drives from NYC to my city, Toronto. We talked on Facebook and chatted for a couple months before he comes to see me. Just friendly stuff. But he’s nice and I have fun talking to him, so why not? We do the usual first date stuff, dinner and a walk on the beach, and he stays the night at my place. I ain’t no floozy! But he drove eight hours to see me, what was I supposed to do?
He tells me he wants to move to my city, we should get married so he can become a citizen, I won’t have to work because he’ll support me. He talks about kids (a boy and a girl). Explains how he thought about it on the drive up, and decided he’s going to sell his house because he hates his life and I’m the best thing to ever happen to him. He left that day to make it for work the next morning, then half way there decided to drive back because he missed me. He stayed in a hotel near my house for two days just to be closer to me.
When he finally went back, he called me pretty much every day before he went to bed and told me my voice made him feel safe. He asked me once if it would be okay to keep our webcams on while we slept, so he could watch me sleep and feel like he was with me. Got upset and cried on the phone when I told him I didn’t want to webcam-sleep with him.
I feel like if it had gotten any more serious (i.e, another ‘date’), and then I broke off all contact, he might have started stalking me. He mailed me two handwritten letters after I cut all online contact with him, and on the odd occasion when I sign on to AIM (to this day) he has cryptic away messages about me. ‘You were the best thing to ever happen to me, [my initials]’ kinds of things. Tip of the iceberg.”
No Wonder She Wouldn’t Let Him In The House
“Six months ago, I started talking to a girl from an online dating site. She was sweet, kind, and pretty. After a few weeks of chatting, we decided to meet and go see a movie, her suggestion. Turns out she only lives a few blocks away from me. I pull up in my car and wait for her. Normally I would have gone to the front door, but she asked that I text her when I was out front and she’d meet me at the car. I sit there waiting for 10 minutes and she finally comes out. So does her cousin, and her cousin’s boyfriend. She tells me that they’re coming along. Great.
Her cousin is loud and, I’ll be frank, ugly as sin. And her cousin’s boyfriend is pretty trashy. He and her cousin like to smoke a lot of ‘doobies.’ I know this because all the way to the theatre that’s all those two would talk about. The girl I was meeting was pretty quiet the whole way through. We get to the 3D movie, and 20 minutes in, her cousin has a panic attack over the 3D giving her a massive headache. Her cousin then proceeds to leave and re-enter the theatre about 50 times. She smells bad, is loud, and has no respect for the people trying to watch the movie at all. The movie ends and we all go outside. Her cousin then proceeds to grind on her boyfriend on the bench out side while they share a smoke.
Fast forward 30 minutes and I drop them off at home. I say good night and speed away. This is where the story should end. But half way home, I get a call from the girl asking that I come over and chill out with them. I honestly wanted to say no, but I figured I wasn’t doing anything and this might turn out to be something funny to tell one day. I go back and enter her house. I now know why she had me wait outside when I picked them up.
The main floor of the house looks like an episode of Hoarders. It was filled with trash. EVERYWHERE. I keep my shoes on and ask where the washroom is, having a big drink at the movie had me wanting to pee pretty bad. I find the washroom, flick on the light and there is urine and poop all over the toilet. On the seat, on the tank, around it. I pee and flush with my foot. I touch nothing. I even managed to turn the door knob with my elbows.
Anyways, after that I sat for an hour watching TV and playing with two very cute cats. I ignored everyone for the most part. I caught bits of conversation between her cousin and her boyfriend. Lots of dirty talk. It made me sick. So after the hour was up, I tell the girl that I have to go. I have to be up early to do make an appointment at the bank (lie).
She walks me upstairs and as I’m saying good bye at the front door, about 10 cats that I hadn’t seen before literally EMERGE FROM THE GARBAGE IN THE LIVING ROOM. I left, and hadn’t talked to her for about 6 months. Last week, she messages me on MSN. She asks me how I’ve been, I tell her I’ve been ok. She tells me she has good news, I ask what. She tells me she’s getting married. ‘Oh that’s good. To who?’ I ask.
She says ‘John.’
I say, ‘Who’s John?’
She says, ‘The guy we went to the movies with.'”
This Was Just The Kick In My Pants I Needed
“I took a girl out for sushi as a first date. About ten minutes in my boss calls. Ordinarily, I wouldn’t have taken the call, but this is not the kind of guy you ignore. I went outside to take the call where the guy berates me throughout the entire conversation. He ended it by saying he’s sorry he interrupted my dinner but, he’s not sure I get what it takes to be his assistant. I walk back in, my confidence utterly destroyed and proceed to be completely in my own head for the rest of the date. As I dropped her off outside her house, she says, ‘You might be the most awkward person ever.’
The next day I was fired.
Getting fired was actually one of the best things that could have happened to me. It lit a fire under me to pursue my dreams. I was ready to move on, and this was just the kick in my pants I needed.”
This Guy Was Way Worse Than Scatterbrained
“I was on a date with a guy I knew from class. We went to a local bar to see this Nirvana cover band he loved. I wasn’t half as excited about a Nirvana cover band but sure, why not?
The band is taking a long time to set up and he suddenly decides he wants a candy bar. Just out of the blue, he says, ‘I want a candy bar.’
I’m a bit confused and ask if he wants me to go with him. He says no, he’ll be right back. I was already getting the, ‘Well, I’ve been ditched’ vibes as I watched him walk out and head to the gas station right across the street.
He did not come back after about an hour and did not answer his cell phone. I decide to head home and, of course, my car won’t start. Thankfully, my friend came to pick me up and listen to my woes.
Cue to the next time I have class. He actually approaches me and acts as if nothing happened. I ended up asking if he ‘went all the way to Hershey’s for that candy bar’ and he brushes it off as just being scatterbrained. Yes, his excuse for never coming back was that he forgot he was on a date.
About a year later, he had a complete mental breakdown, thought he was a middle aged marine, bought a Ferrari he couldn’t afford, and he killed a friend while driving under the influence.”
This Must Have Been Beyond Uncomfortable To Sit Through
“I talked to one guy for a while over messages and text and he seemed pretty cool. Decent enough looking photos, seemed a bit shy and nerdy but that’s okay. He was into gaming but then again, hey, so am I. Finally, he asked me out to coffee just to meet and I agreed. So far as I understood and we agreed upon, it wasn’t a date. It was just meeting.
I dressed as I usually do. Clean, not ratty, regular looking clothes, showered, hair brushed, teeth brushed that morning. He showed up in the rattiest looking clothes I’d ever seen full of holes and stained, full neck-beard, looked like he hadn’t shaved in a week, smelled like he hadn’t bathed in 2 weeks, with discolored nasty looking teeth with bits of stuff between them. We showed up at the coffee house and went to the counter to order. I ordered something and the barista took his order as well. When she asked if they were going to be on the same check, he blurted out, ‘Yes,’ then walked away to a table, leaving me to pay for both drinks AND carry them back to the table.
I placed his drink in front of him, he looked down at it then back up at me and flatly informed me he took his coffee with 2 sugars and cream, then sat back in his chair and glared daggers at me. I should have told him to shove it and left, but I stupidly took his drink back and doctored it up for him, assuming that maybe he was just very socially awkward and brought it back to him. He took a sip, gave me a disgusted look, and pushed his drink away from him towards my side of the table.
For the next 15 minutes I tried to initiate conversation about something, ANYTHING. He just grunted one-word answers like, ‘yes, no, maybe, I dunno’ as he looked around the room at walls, paintings, other patrons, and my chest, still sitting back in his chair with his arms crossed.
At that point I got up and left. I didn’t say a word, just took my coffee and walked out, drove home, and had a shot. I got a message from him the next day online asking me why I had been “such a witch to him.” I deleted my account and blocked his number from my phone. I still to this day have no clue what all that was about.
The whole time he acted bored, completely uninterested, and annoyed. It felt like I was wasting his time, and it definitely felt like he was wasting mine as well. I really did feel very bad for him until I got his email the next day calling me a witch.”
“The Cat Dies In My Arms”
“I met a flight attendant at a local bar and hit it off. The next week, we met again and went back to her place, which she shared with a roommate and the roommates’ boyfriend. We were there all alone. The roommate had a new kitten, really cute and sweet. While massaging the girl, the kitten kept on jumping up on her, being a pain but in a cute way. She was going on and on how much she loved the kitten.
Anyway after a little while, I figured I was going to get lucky that night when her roommate and boyfriend came home. I’m not sure what started it anymore, but the girl I was seeing and the roommate started fighting and screaming at each other. At one point, the girl I’m seeing decides to leave. She runs out of the apartment and slams the door behind her.
Little did she know the kitten was following her. Yup, she slammed the door on the kitten. The kitten starts twitching. The roommate is freaking out over her cat. A few minutes later, the cat dies in my arms.”