Real Life Stories of Truly Awful First Dates

Real Life Stories of Truly Awful First Dates June 2, 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.

A Shoe In


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


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 at a local country club for the next afternoon.

So the first few holes went well but then the 7th hole happens. I'm about 230yds from the green so I pull out my 3W. I see the pair of sandhill cranes they were about 150 yards down the fairway so I paid them no attention.

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. We played the last 2 holes with maybe exchanging 10 words. Didn't hear from her again. Story credit: Reddit / rektt



I decided to meet up for coffee with a girl that I had been talking to online. We talked for 45 minutes or so - normal first date topics like family, travel, etc. She then asks, "where did you do your undergrad?"

Now, I have a pretty good job, but that question sets the bar pretty high for a guy who didn't go to college. She is not only assuming that I went to college but is also assuming that I am taking part in some type of post-graduate school.

When I said that I went to technical school and then straight into the workforce she looked at me as if she'd never heard of such a thing. Apparently, I didn't pass all of her minimum requirements to be considered human.

After a brief pause, she broke off her shocked stare, placed her hand on her forehead in a fashion that covered her eyes, inhaled briefly and followed it by a valley-girl, "eew!" She took her Blackberry out of her purse and whispered to herself as she typed, "he ... didn't ... even ... go ... to ... college ..."

I then saw the left thumb hold the shift key as she deliberately pressed the exclamation point key once... ! Twice... !! Three times... !!! In reality, each one of those keystrokes was a simple tapping of a small piece of plastic, but, in my head, it sounded like a metal bank vault door was repeatedly slamming shut.

She pressed a few more buttons on the phone, presumably sending this text message to her total BFF. She put the phone away, looked at me, and after taking a deep breath said, "well that is okay. Not everybody is capable of going to college."

She put on a fake smile followed by an awkward laugh and just stared at me awkwardly. I couldn't believe that she'd react so rudely to something and then try to act as if it didn't happen. Perhaps she still believed that, like a child playing hide and seek, if you covered your eyes you would disappear.

After staring at each other awkwardly for a few seconds, I finally broke the silence by saying, "Wow, okay. So, yea... I, uhm guess it is about time to get out of here?" I stood up and took my trash to the trash can and she followed me out the door.

I turned and began walking down the street and she followed closely and said, "how far away is your car?" This girl was expecting a ride! So, I stopped and turned around and said, "oh, I am about a block this way. Where did you park?"

She replied, "Oh, I took the bus here. I don't have a drivers license." Now, I am normally not a rude person. Even in that situation, I was going to just walk away and let that be that, but I just couldn't pass this opportunity up.

I looked at her right in the eyes and said, "eew!" Pulled out my cellphone and typed, "she ... doesn't ... even ... have ... a ... license ... ! ... !! ... !!!" I then put my phone away, looked up at her, smiled and said, "That's okay! Not everybody is capable of driving a car! Lucky for you, the bus stop is right over there. I hope you don't have to wait too long!"

I wish I took a picture of the look on her face as I walked away. It was priceless. Story credit: Reddit / kid320

Mixed Signals


A regular customer of mine who knew I had a new bike asked if I wanted to go on a cruise with him later on in that week. Happy to have someone to ride with, I accepted.

Friday comes and we meet up at my work (Starbucks) grab a few bottles of water and then we're off. Halfway through the cruise we stop and grab a coffee at another Starbucks and chat for a minute. We continue 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; there was no one else in sight, which was rather odd timing.

He's sitting on my left. There's a long moment of silence. 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. (note to self: stop being too nice to customers) Embarrassed, he jumps on his bike and speeds away. It took us an hour to get there, but since I didn't even know what part of the beach I was at, it took 3 hours for me to get back to my car.

So I guess what I'm saying is that, 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

Of Course She Was a Karen


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

Mocking the American


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. On a lark, I accepted - I was rebounding off another man and my standards were pretty low.

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 (probably about 5 minutes to empty) 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


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


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. No biggie, she was still cute and I hope I am not that shallow. However.... First thing I disliked is she wanted to sit in the front freaking row of the movie theatre.

Still, I decided, people have dealt with much worse. 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 to play some Counter-Strike. Story credit: Reddit / Krypty

Tainted Love


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

Bathroom Break


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

End of Date


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

Clearly Everything Worked Out


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

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

Whine and Dine

Wikipedia / Clotee Allochuku / CC 3.0

I went on a date where the boy planned to take me to some small fancy restaurant. I hadn't seen him in a while, we met at a friend's party, but we had been texting for a few weeks and he seemed awesome.

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, all the while he's still complaining about how terrible that date is. 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!


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 to close off the night properly. When we were going through the exit turnstiles (that only move one way), she got her toes stuck under them.

she started freaking out and yelling at me angrily saying her toes were broken/fractured until the ambulance got there. when the paramedics arrived they untrapped her toes within 3 minutes.

We drove 30+ minutes to the hospital and were stuck there for hours with her badgering me about how much pain she was in as she sat in a wheelchair. 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


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"- his only hobby was weightlifting, which I know nothing about (though I asked a lot of questions).

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" and that he "couldn't date a girl who didn't do sports".

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

Never Let Them Know Where You Live


Just moved to Chicago, was very lonely. This ridiulously hot Russian guy asks me out at the bus stop. 2 weeks later we go on a date. He did tee-shirt designs and I am a pianist so for our first date we were going to give eachother a lesson on our craft.

This was a huge mistake for me. My piano is in my apartment, and I live alone, and I don't know this guy, but Im young and dumb, he is incredibly hot so I let him in. I should have run then.

Fast forward, the boy starts going through my things, he chokes my cat, knocks my closet door off of the track. Now Im scared and I need to get him out of my apartment in the smoothest way possible.

We leave, and go have Thai food. Why I was still putting up with this, I cannot tell you. He sits on the same side of the booth with me, and burps (with purpose) in my ear, he also conveniently didn't have any money and I had to buy his dinner.


As we left and started walking down the street, he flicked a penny at a homeless person, made fun of the sculptures on the street, and screamed at a lady's poodle walking down the street. It was then I took off RUNNING away from him. I ran back home, hoping he couldnt remember where I lived.

He did. Someone hours later, let him into my apartment building. I get a knock on my door, I look out the peep hole, its him. I'm about to call the police, but he runs away when I threaten him with it.

Yeah, he blew up my phone for 2 weeks after that. Thought I was gonna have to move. Story credit: Reddit / [deleted]



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

The Long Dress Story


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


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


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

Accidental Kidnapping


About 4 years ago I went out with this girl I met at a summer camp we both worked at. Camp had ended and I had agreed to drive the hour between our houses and pick her up for a night of teenage romancing.

I had spent a number of hours deciding on which restaurant I would take her to, then where to go after, even down to what time I would take her home. 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 had her hop in and we were off.

Dinner passed and was uneventful, consisting of me trying not to make a fool out of myself so that I would have a chance with her at the end of the evening. After dinner I suggested that we go to a cafe around the corner for dessert.

We ended up splitting a slice of cheesecake, which was how I knew I was doing well with her. It was starting to get more than a little flirtatious, hand holding and that sort of thing. I have noticed the entire time that she kept ignoring a phone call from someone, but once again I still didn't think to question it.

As we turn on her street, we are greeted with four cop cars parked outside of her parents house. Her response: "I didn't think they would do that." I pull up to the house, in time to have 4 armed police officers tell me to step outside of the car with my hands up.

In the next 15 minutes I learned that the girl was not 17 like she had said she was, but actually 15. She had lesbian parents who had disallowed her to see me, so she had snuck out to go on the date with me.

Her parents had called the cops informing them that their daughter had been kidnapped, and so there I was an hour away from home being questioned by the police. Eventually everything was dropped and I was allowed to go. Story credit: Reddit / squaresoccerball

The Goth Litmus Test


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


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

Bravery Incarnate


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


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


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


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


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.

Tl;dr: I got knocked in the head by a low talker and I'm Catholic. Story credit: Reddit / hot_assistant

Prince Charming


I met this guy at a friend's house during a small party and really hit it off, and we agreed to go out later that week.

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 or two before we left to go out, 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. When we got in my car, he kicked his shoes off and plastered his dirty feet against the inside of my windshield. I should have turned around at this point, but we went to the bar.

The bar was nothing special, and I said I was ready to go after one drink. When I got back to my house, he tried to shove his tongue down my throat, and I did the awkward face turn and got his tongue on my cheek.

He then retrieved his four remaining beers from my house and left. We never spoke again. Story credit: Reddit / conundrummed

Overly Attached


I'd have to say my worst date was overly attached guy. I met him in a calculus class at my university. 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 since we just started seeing each other 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


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


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


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


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


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


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


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


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]



When I was a grad student I was a regular at a cafe near my home. Down the street from the cafe were a few retail shops behind glass windows. I used to walk by them on the way to the cafe.

One shop wasn't particularly busy and as I walked by I would always make eye contact with the girl who worked in the shop and give her a smile.

One day she came into the coffee shop. It was busy, so I invited her to sit with me. We talked a bit, exchanged names, and had a nice time for the ten or fifteen minutes we sat together. A few days later, she saw me walking by her shop and she came out of the shop to give me her number.

I called her that evening and we talked on the phone for hours. I kept trying to get off the phone, but she was a great conversationalist and kept the conversation going. It was fun. I don't think I had ever spent so much time on the phone. Before we finally hung up, we arranged to go on our first date.

Friday night and I pick her up at work. She was like fifteen minutes late, which was no big deal, but she was really apologetic. On the way to the restaurant, I try to make conversation, but she is mono-syllabic. At the restaurant, the "conversation" was punctuated with long silences.

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. I thought she looked great, but my only response was, "Why do you say that? It's totally not true." More silence ensued.

The drive home was mostly silent but met with another out-of-the-blue comment. She said, "I don't think I could date someone who isn't close with their parents." It sounded like an accusation. I didn't know what to say to this. My parents and I are quite close, but I didn't want to sound defensive, so I let it go.

When we got back to town I asked where her home was to drop her off. She gave vague directions, then told me to pull into a convenience store. At the convenience store, 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. Some time later the store closed. I never saw or heard from her again. Story credit: Reddit / whittlingcanbefatal

Sk8er Girl


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



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



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



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



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



This happened while I was working at a bar. Had a girl come in alone, 20's, dressed nicely, nice hair/makeup etc 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. Long story short I don't think there was a second date. Story credit: Reddit / clover_01

Snapchat Date


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 and stuff.

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 with his voice shouting the same line over and over 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 with her in it. For like 45 minutes this goes on and then they get up and leave. Story credit: Reddit / Brak23

Trash Date


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


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



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. She didn’t mention anything about that before. 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