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Real Life Stories of Truly Awful First Dates

Real Life Stories of Truly Awful First Dates August 6, 2022Leave a comment

Let's be honest: first dates can be really scary. Things don't always go according to plan, and opening up can be embarrassing. Some first dates, though, are worse than others, as these true stories of terrible first dates make very clear.

End of Date

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We arrive at a nice restaurant for dinner. Idle talking while we're waiting to be seated.

"Oh that's a nice ring." "yeah I love it. My boyfriend gave it to me for our anniversary yesterday." LOLNOPE. Story credit: Reddit / Uncle_Oj

Romance at Walmart

Wikipedia / MikeMozartJeepersMedia / CC 3.0

I went on a first date with a guy and after seeing a movie he told me he really wanted to go to Walmart. So we drove over there and before we got out of the car he asked me if I wanted to make it "official".

Even though I said no we still ended up going into Walmart together and I watched him shop for DVDs. Story credit: Reddit / Retawekaj

The Long Dress Story

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She complained about every other girl that walked into the restaurant we were in, and then the bar afterwards. She also told me about her inability to choose what dress she wanted to buy when shopping the week before...for 20 minutes.

She also told me everyone she had ever gone out with and why she had split up with them. I cut the date short by saying I was tired, put her in a cab, deleted her number and went and got drunk with my friends. Story credit: Reddit / KrazyEyezKilla

Two Hours

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I went on a date with someone I knew for a total of two hours. I was his first for everything. He told me he wanted to marry me. TWO HOURS. Story credit: Reddit / aishaaa

Oh Deer

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First date, dinner with a girl I really liked. When leaving, I back my car into another persons car. Embarrassed, but I handle the situation, exchange info, etc. While driving her home, I hit a deer. I got out of the car to evaluate the damage and discover that the deer is alive and suffering.

No animal control to euthanize, so I did the humane thing and ended its suffering (in a quick and respectful manner). Awkwardness ensues. We never had a second date. Story credit: Reddit / dinnertainment

The Goth Litmus Test

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When I was in college, I had a blind date with a guy from out of town. I wasn't overly familiar with the area's attractions and relied on him to pick a place. BIG mistake!

He offered me pizza for lunch, but wanted to eat it somewhere romantic instead of inside the pizza shop. Apparently his definition of romantic was a cemetery, so for my very first ever college date I had pizza in a cemetery. Story credit: Reddit / bootchker

Lactose Intolerant

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Didn't end bad, but on my first date with a girl I asked what she wanted as an appetizer and she said she didn't care, anything's fine. So I went the safe route and ordered the combo/sampler of mozzarella sticks, potato skins, hot wings and a spinach and cheese dip.

She's lactose intolerant and also unable to eat spicy food (she literally thinks Italian dressing is spicy). So I ate the whole thing and we celebrated our 5 year anniversary last month... Great girl, and easy to cook for. Grilled Chicken. Story credit: Reddit / DirtyMonday

Tainted Love

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First date I ever went on was when I got my first kiss. After we smooched I looked at her and said "… I love you". After that we just stood there for 30 seconds and then I just said good night and left in the most awkward way possible.

The next day I explained that my response was a "heat of the moment" kind of deal; and things were fine after that. I was 15 at the time. I still look back on it and think to myself what the hell were you thinking?! Story credit: Reddit / yahtz33

Clearly Everything Worked Out

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I fainted on my first date with my husband. And I hadn't showered before the date, after a five mile run. Story credit: Reddit / oddfell

Of Course She Was a Karen

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In 4th grade, I used my birthday money from Grandma to take the lovely Karen H. roller skating - not just a 1st date - my first date, ever.

Once we got there (thanks for the ride, Mom) we went around a couple times, then she started skating with an older boy, I fell down (1st time skating, too) and somebody rolled over my fingers.

She never said "thanks for a lovely time" or anything. Story credit: Reddit / Leatherhead_jarneck

A Shoe In

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A guy I work with had an awkward one. He's recently divorced and this was his first date since the split. After dinner they decided they were going to walk around the city. She says she wants to drop into this shoe store real quick.

The woman then proceeds to try on shoes for 45 minutes, and then my friend just decided "I guess this is is my cue to leave". Says his goodbyes as the woman continues trying on shoes, completely unfazed. Story credit: Reddit / VisitChechnya

Hitting a Birdie

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Met a girl in a college class and noticed she was looking at golf clubs on Ebay. Being a golfer myself I figured it was a perfect conversation starter and went with it. After an exchange of numbers and some conversation we had a golf date.

So the first few holes went well but then the 7th hole happens. I take my swing and to my surprise the ball was a low line drive that got no more than a few feet of the ground. And to my surprise one of the birds was in the way of the ball. It was a direct hit to the neck and the bird went down for good.

Sandhill cranes mate for life so when one of them dies the other will sit there for hours crying for the other one. It was sad, but little did I know she LOVED these birds and the look on her face was horrific. She broke down in tears. Didn't hear from her again. Story credit: Reddit / rektt

Mixed Signals

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A regular customer of mine who knew I had a new bike asked if I wanted to go on a cruise with him. Happy to have someone to ride with, I accepted. We start the cruise and wind up at this beautiful part of the local beach I didn't even know existed.

Things began to feel a tad bit off at that point, but I didn't think much about it. We parked the bikes and chill out on a log overlooking the water. I look over to my right, gazing at the scenery, and I feel a hand on my leg. When I look back to my left he plants a wet one right on my lips.

I stand up and scream out of shock. For some reason, he thought I was gay. Embarrassed, he jumps on his bike and speeds away. The worst thing that happened to me on a first date is not knowing that I was on a first date. Story credit: Reddit / ViciousMountainGoat

Mocking the American

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After months of trying to text me late-night and me laughing him off with the 'Yeah, you can buy me dinner first" he offered to take me out for drinks. His friend 'just so happened' to be drinking at the same pub we went.

They stood at the bar not ten feet from the table we were sitting at, and every time this guy drained his drink he'd go up to the bar and chat with his friends. This was obnoxious enough, but on his third little chat, they were all drunk and started talking about me - my looks, my accent.

I was 10 feet away and it was not loud enough to drown out their conversation. He was so distracted complaining about this American girl that he didn't notice me walk by him and out the door. Story credit: Reddit / [deleted]

There's a Reason He's an Ex

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I once had an ex who refused to accept our breakup. He saw me at a bar with some other guy and tried to tell my date he was still my boyfriend.

I tried to explain that we were broken up, but the date was pretty much ruined once my ex showed up, sloppy drunk and screaming about how I was cheating on him in front of his face. There's not much you can do to really salvage a date under those circumstance. Story credit: Reddit / geebsterlove

Front Row

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The only time I went on a date with a girl I met on the Internet was a fantastic failure.

As I imagine in most cases, when I saw her in person, she wasnt as attractive as her pics let on. She was still cute and I hope I am not that shallow. First thing I disliked is she wanted to sit in the front freaking row of the movie theatre.

But then it got absolutely fantastic - a friend of hers shows up, and these two are pointing, laughing, and screaming their heads off and calling random characters 'gay' and whatnot. At this point I had decided my time had come, excused myself to the bathroom, and went home. Story credit: Reddit / Krypty

Bathroom Break

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I was on a first date with a cute girl that was going really well, when suddenly I was overcome with a violent case of Montezuma's revenge. I calmly excused myself and walked to the bathroom as fast as I could without it being obvious that I was sprinting.

I managed not to destroy any of my clothes, but it took me about 10 minutes to clean the bathroom up and douse myself with the air freshener spray they had in the bathroom.

When I came back, she was gone and the waiter was standing next to the table. He had asked my date where I went, and she started crying and stormed out. She never returned my calls or texts after that. Story credit: Reddit / showboats

Whine and Dine

Wikipedia / Clotee Allochuku / CC 3.0

He picks me up, spends the entire time driving to the restaurant complaining about his day. We get to the restaurant too late and its closed, so he complains about that. His friend calls him while we're looking for a new place, he answers and complains about how this date is so bad.

We ended up eating at IHOP. Now I know he meant it was terrible in that we didn't get to go to the other restaurant and ended up at IHOP, but in my opinion a date is good or bad based on if you have fun with the other person, so I took it personally.

At the end of the night he drops me off and tells me he had a great time even though it was a terrible date and he would like to see me again. Didn't happen. Maybe if he hadn't whined the whole time I could have had fun too. Story credit: Reddit / Blue_no_Yellow

Oh, The Pain!

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Took a coworker of mine to a baseball game - we had a great time. Got pretty drunk and took the subway back to my house. When we were going through the exit turnstiles, she got her toes stuck under them.

She started freaking out and yelling at me angrily saying her toes were broken until the ambulance got there. When the paramedics arrived they untrapped her toes within 3 minutes. We drove to the hospital and were stuck there for hours with her badgering me about how much pain she was in.

Once we got the x-ray back at 6am we found out there was absolutely nothing wrong. I paid for the expensive cab across the city back to mine and put her to bed in the guest room so I could wake up in 2 hours to go to work. Story credit: Reddit / chooeybacca

Track Doesn't Count

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I go to a large university, so it can be hard to meet people in class. Luckily, I had a couple of small discussion sections one semester and hit it off pretty well with a guy in my Shakespeare class. We decided to go on a date to a local cafe.

He and I had nothing in common outside of liking Shakespeare. He only talked about weightlifting and "bulking up." He started berating me for not weightlifting and asked what sports I played in high school- I was a cheerleader and ran track, which he said "didn't count."

I can run a half marathon, know all sorts of elaborate jumps, and I'm pretty flexible... but no, those aren't sports. Story credit: Reddit / coldsandovercoats

Creep

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I went on a first date with this guy (also the first real date I've ever been on) and it was totally creepy! The majority of the time he spent talking about his home town and how he couldn't get a girl friend.

He then continues to tell me that his roommate went home for the weekend and asked if I wanted to go hang out in his dorm and drink. I then texted one of my friends to call me and acted like I had to leave right that moment. It was the scariest thing ever! Story credit: Reddit / jjawesomesauce

Bravery Incarnate

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I was on a first date with a guy who pooped himself. He did manage to tell me what had happened, and we handled it effectively.

We were at the beach, I instructed him to get in the water, away from everyone else, and get himself a bit sorted out. Then I went and bought some alternate shorts for him. It was awkward, but I appreciated that he just plain told me what was going on, rather than trying to cover it up or something.

Seriously, he got major points for manning up and telling me what was going on. Other dates followed, though the relationship didn't work out. Story credit: Reddit / oddfell

All's Well That Ends Well

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I'd been friends with a girl for a while through high school and college. We'd hung out at school/parents' houses/parties so we knew each other well. I eventually convinced her to date me. Being 19 and in suburbia, the Olive Garden was the nicest place I could think to take her.

The dinner was uneventful and pleasant. As we were driving back to a friend's apartment, we sense that something is greatly amiss in our stomachs. We're just kind of looking at each other nervously as I'm driving and I know she's thinking the same thing I am: "hurry up and get to the apartment."

As we run through the door, we're greeted by a single, unoccupied bathroom. We spent the rest of the night taking turns delivering relatively undigested salad, breadsticks and chicken parmesan to the Clayton County sewers. Six years later, we married. Story credit: Reddit / semisimian

The Waiting Boyfriend

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I liked this girl when I was in high school. We talked and joked around all the time. Well, I finally worked up the nerve to ask her out to concert. We go to the concert and everything's going pretty cool, she leaned up against me for a while and we hugged a few times.

When we left, I asked her if I could take her to get something to eat, and she says, "Nah, my boyfriend is waiting for me." My stomach dropped, and it took everything I had not to let my anger show. I never talked to her again. Story credit: Reddit / ChuckZombie

Unexpected Double

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First date back in high school with a girl I barely knew. We were meeting at a movie theater I wasn't familiar with, and at the last minute she told me she was bringing a friend (WTF), and asks if I can bring one. So, I convince one of my friends to come, and so begins the most awkward date ever.

Her friend and her completely ignored my friend and me, we ended up being late to the movie (their fault), awkward conversations the whole time, never talked to each other again. Story credit: Reddit / [deleted]

Catholic Guilt

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I had just graduated from high school and it was the summer before college… I met a very shy guy who worked at the ice cream parlor next to the restaurant I worked in. After a few flirtatious meetings, he finally asked me out to a movie.

He was a very low talker so I basically nodded and smiled after so many "excuse me's?" and "huh's?" during the movie he tried to put his arm around me and knocked me in the face with his elbow.

To top it all off, we had to leave the movie early because of his 10:00pm curfew and I couldn't come hang out at his house because I wasn't a Born Again Christian. Story credit: Reddit / hot_assistant

Prince Charming

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I met this guy at a friend's house during a small party and really hit it off. On the first date, he showed up to my house and rang the doorbell with a six-pack of PBR in his hand. He then told me that he needed to use my porch to smoke a cigarette, and by the way, "what do you want to do anyway?"

I sat on the patio with him while he chain smoked and suggested that we maybe just grab a drink somewhere. He then pounded two beers, threw the empty cans on the patio, and walked back inside. I was flustered at this point, and just went with it and followed him back into my own house.

He then told me that he couldn't drive because he rode his scooter, and I'd have to drive. The bar was nothing special, and I said I was ready to go after one drink. He then retrieved his four remaining beers and left. We never spoke again. Story credit: Reddit / conundrummed

Overly Attached

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I'd have to say my worst date was overly attached guy. We hit it off talking about random stuff and found out we lived relatively close to each other. We went on a couple of dates one being at the Zoo.

Mind you it's mid July and around 90+ degrees Fahrenheit out. He insisted upon putting his arm around me after I asked him to stop because it was so grossly hot out and we were sweating. After a couple dates I decide he's not too bad and have him over for a party with my friends.

He spends the entire party at my side including having his arms around me while I cleaned up. Deciding he's too clingy, I call him and break up with him. He then starts yelling at me how I was just using him. Note we never did more than make out. Story credit: Reddit / RoriPanda

My Date with a Vampire

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I went on a first date with a guy I had met online. Everything was going really well - we were just sitting next to each other, talking, and drinking coffee. well, that's not true - he was drinking chocolate milk. In hindsight, perhaps this should've been a red flag.

the conversation is going really well, we've got a lot in common. all of a sudden, he just stops, looks at me, leans over, and BITES my neck. not in a soft nibble sort of a way, we're talking full on vampire chomp.

I jump away, fully expecting to need stitches or something based on how much it hurt. Thankfully, he didn't break the skin. If I hadn't dropped my coffee when I jumped away, I probably would've thrown it on him. Story credit: Reddit / patchworksheep

Whole Lotta Nope

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I went to a "theater" performance she was in where they brought people on stage and did things to them as part of the "act" but really that was the whole thing. They made me close my eyes strapped me into a chair and then tried to put a cockroach in my mouth repeatedly.

I blew it out of their hands and it fell on me and then they picked it up and tried again. After a few minutes they asked me "how scared" I said 10/10 and they let me out. Story credit: Reddit / Apostolate

Locked Out

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It wasn't so bad seeing as we still laugh about it to this day, but in February, I locked us out on my balcony at 2 in the morning. It was cold, he ended up having to climb down from my second story balcony, trudge through two feet of snow, climb a fence, go up to my door to unlock it.

He had a hard time unlocking it because it's a difficult to open one. He thought it wasn't the right door, so he went back outside, back out around the back of the building to ask me which apartment it was. Went back and finally opened the door. Story credit: Reddit / jangutigirk

Slip of the Tongue

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Went in for the kiss and didn't know if she wanted open mouth or closed. So I did both awkwardly. It was the worst kiss of both our lives. There was no 2nd date.

8 years later she sent me a Facebook message saying she was sorry for not going out with me because of that. I'm scared to make out now. I married somebody who thinks tongues are gross. So I never have to worry about this ever again. Story credit: Reddit / [deleted]

Free Puppet Show

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Date met me at the restaurant. Proceeded to tell me his dream of doing a comedy puppet show (ala Crank Yankers) and then does all of his characters he's come up with. Got the voice, the hand movements, everything sans puppets. He's really loud. People are starting to stare.

I'm feeling increasingly awkward. He starts talking about what we should do on our next date. At the end of the date, he asks for a ride home because he doesn't have a car and the bus ride back to his apartment would "take a really long time". I declined. Story credit: Reddit / sweetcorny

Bad Timing

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Girl and I had been trying to see each other for a while, live 100 miles apart and both pretty busy, and finally got a chance for a first date.

Fast forward to the day. It's going well until after a few hours her mum calls and continually redials when she ignores it the first few times. She ended up answering it only to be told her dad had just had a heart attack and passed away. Date ended pretty quickly. Story credit: Reddit / [deleted]

A Smashing Date

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Worst thing I've done on a first date was swerve between lanes through construction cones very suddenly, causing my date to smack the side of her head into the window in the passenger seat. We both laughed pretty hard about it, but I felt realllly bad about it. There was no second date.

I told the next girl I dated the story and told her as she got into my car for the first time, "I'll try not to smash your head haha" and she replied "I'll try not to be an idiot and let you". Had to laugh. Story credit: Reddit / kingofspoonerisms

Locked Out

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On my first date with my current gf, when I picked her up I got out of the car (left key in ignition to keep car cool) and knocked on the door, then i walked her to my truck and when I tried to open the door for her it was locked!

Worst feeling ever! Locked myself out of my truck and had to call my brother to bring the spare. Story credit: Reddit / [deleted]

Sk8er Girl

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I knew a girl who told me she'd been "skating" forever, that she was on the national skate team, etc. I'm like, cool cool, tell me more. She talked about her friends skating with her, all good. After no less than 7 months of regularly talking, she invites me to a "skating performance".

I'm asking, what will they perform? She says, "the nutcracker". And I go, 'oh wow. That's… Interesting. So will you make up for the dancing with a skateboard performance?'. She looks at me in disbelief, bursts out laughing. Obviously, she was an ice skater. Not sure why that never crossed my mind.

I totally imagined her to be a sk8er girl, from her personality, that'd have been a fit. Oh well. The nutcracker performance was dope, though! Story credit: Reddit / rhababerbarbara

Understandable

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One girl started crying when a certain song came on and demanded to be taken home, maybe 20 minutes into the date. I guess it reminded her of her dad that had passed.

No hard feelings on that one, obviously. I did my best to cheer her up on the way home. Never heard from her again. Hope she's doing alright these days. Story credit: Reddit / roachezmo

Moneybags

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Had a girl try to convince me to cut off my long hair for the date. The first date. She knew I had long hair, it wasn't a blind date. She also brought her dog unannounced, insisted it go into the bar with her, then only talked about money for the next hour or two, constantly pestering me about how much I made.

The second I caved in the date was over. Ms. Moneybags still let me pay the tab. Story credit: Reddit / roachezmo

Chaperone

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I asked a college girl out for dinner and to see a play and she invited her mother along. It was so awkward. Story credit: Reddit / airmaildolphin

Moose

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I was walking past a rickshaw one night with a dude and a lady in it, and the lady says, "I always feel bad for these guys, I feel like I'm too heavy."

And instead of reassuring her the guy says, "Oh don't even worry about it, these guys could carry a moose!" I think he knew as soon as it left his mouth that he wasn't getting anywhere on that date. Story credit: Reddit / BigShoots

Mismatched

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Had a girl come in alone, 20's, dressed nicely, you could tell she'd gone the extra mile. She ordered and waited for her date at the bar, looking nervous. Then this guy strides in through the door wearing full grey tracksuits, looked like he just got outta bed, and boldly exclaims "YOU ALRIGHT LUV?!".

I wish I could describe the look on her face. It was over before it started. Lucky for me they took a table in front of the bar so I could watch how it all went down. She was already somewhere else, and her bathroom breaks became longer and more frequent.

Each drink the dude had took 2 years off his age and increased the ferocity of his hand gestures, by the end of it we had a beautiful, uncomfortable and angry girl with a drunk child in man's clothes. Story credit: Reddit / clover_01

Snapchat Date

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I was in Maui for vacation and walked over to eat at a restaurant near my hotel. I sat next to this couple who were just sitting down as well and they had some light small talk and ordered drinks and food.

He pulls out his phone and records a snapchat video of her and saying "This is my friend from Utah" and it all seemed like they were hitting it off, then it got weird. He appeared to lose his ability to strike up any conversation, he kept re-watching the video he just took and ignoring her at the table with him.

She kept trying to talk to him and keep things going, but he just wasn't responsive or talking and just kept watching his own video. For like 45 minutes this goes on and then they get up and leave. Story credit: Reddit / Brak23

Trash Date

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I picked up this girl and she gets in the car and before even saying hello or anything she asks me: “Do you recycle?”

I’m so blown back by this question, and pause for a second. “Of course! Who doesn’t recycle?” And she just says: “We’re not gonna get along.” Should have kicked her out of the car lol. Story credit: Reddit / SheilaFromAccounting

Third Wheel

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Good date. Having fun. Good conversation. Enjoying the nice spring weather on the porch of a Mexican restaurant. We have just asked for the check and then a woman shows up and threw her keys at his face.

He pretended it didn't happen. It comes out (pretty quickly) that this was his girlfriend. They get into a right proper fight in the parking lot and the cops show up. I can't leave because my card is inside with the server and it's taking 1000 years. Story credit: Reddit / mophilda

Nope.

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Went to pick her up. Pull up to the house and walked to the door. Rang the doorbell. Nothing. Rang the doorbell again. Nothing. Texted her saying I was there. “I don’t see you.”

Turns out her parents were divorced, and she was staying at another parent’s house that night. So I drive 45 minutes to her other parent’s house. Did she apologize? Nope.

Took her bowling. Apparently, you’re supposed to go a little easy, or whatever, to make it more enjoyable for both people. I didn’t know that. After bowling, we just kind of...drove around. Asked if she was hungry. “Nope.” Asked if she wanted to see a movie. “Nope.” Just took her home. Story credit: Reddit / spwf

Eew

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I decided to meet up for coffee with a girl. She asks, "where did you do your undergrad?" I have a pretty good job, but when I said that I never went to college, she looked at me as if she'd never heard of such a thing. She placed her hand on her forehead and followed it up with a valley-girl, "eew!"

Then she said, "That's okay. Not everybody is capable of going to college." I decided that it was time to get out of there and began walking down the street when she said, "how far away is your car?" I stopped and turned around and said, "I am about a block away. Where did you park?"

She replied, "I took the bus here. I don't have a drivers license." I was going to let that be, but I just couldn't pass this opportunity up. I looked at her in the eyes and said, "eew!" I then smiled and said, "That's okay! Not everybody is capable of driving a car!" Story credit: Reddit / kid320

Never Let Them Know Where You Live

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This ridiculously hot Russian guy asked me out. He did tee-shirt designs and I am a pianist so for our first date we were going to give each other a lesson on our craft. This was a huge mistake. My piano is in my apartment, and I live alone, but I'm young and dumb so I let him in. I should have run then.

The boy starts going through my things. Now I'm scared and I need to get him out of my apartment in the smoothest way possible. We go have Thai food. He sits on the same side of the booth with me, and burps in my ear, he also conveniently didn't have any money and I had to buy his dinner.

As we started walking down the street, it was then I took off RUNNING away from him. I hoped he couldn't remember where I lived. He did. I get a knock on my door, its him. I'm about to call the police, but he runs away when I threaten him with it. Thought I was gonna have to move. Story credit: Reddit

Accidental Kidnapping

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I went out with this girl I met at a summer camp we worked at. When I arrived to pick her up, I was surprised to see her out on the side of the street, rather than in her house, but I paid no mind and we were off.

Dinner was uneventful, consisting of me trying not to make a fool out of myself. After dinner I suggested that we go to a cafe for dessert. It was starting to get more than a little flirtatious. I have noticed the entire time that she kept ignoring a phone call from someone, but I didn't question it.

I pull up to her house in time to have 4 armed police officers tell me to step outside of the car. In the next minutes I learned that the girl was not 17, but actually 15. Her parents disallowed her to see me, so she had snuck out. Eventually everything was dropped and I was allowed to go. Story credit: Reddit

Monosyllabic

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I was a regular at a cafe. Down the street were a few retail shops. One shop wasn't busy and as I walked by I would always make eye contact with the girl who worked there and give her a smile. One day she saw me walking by her shop and she came out to give me her number. We arranged to go on a date.

She was like fifteen minutes late, which was no big deal, but she was really apologetic. At the restaurant, I try to make conversation, but she is mono-syllabic. After one of the silences, she suddenly blurts out, "I'm fat. I look like I'm pregnant." I was taken aback and didn't really know how to respond to this.

When we got back to town I asked where her home was. She gave vague directions, then told me to pull into a convenience store. Then she got out and said she'd walk home from there. I continued to walk by the store she worked in everyday, but never saw her there again. Story credit: Reddit