Dating Gone Wrong! 28 People Share Their Worst Dating Experience.
Dating is a wonderful experience. Planning outings, dinner, movies, long drives and all other creatively romantic ideas. Two people get to know each other, their likes/dislikes and preferences while having a good time together. However, dating is not always fun. Going out with the wrong person can lead to a lifetime of a bad memory. From being bailed on to bailing out of them, getting super drunk and embarrassing ourselves to being stuck with weird heavy drinkers, we have all been on at least one bad in our lives. But how about the worst date ever, no one forgets their worst date ever. Here are 28 such Redditors sharing their worst dating experience.
Chatterbox At The Coffee Shop
First date, coffee shop, I’m expecting it to be <1 hour. The guy talks about himself nonstop, without asking me one question about myself. Every 20 minutes or so, he’d finish a topic and launch into the next one, all of them in a tone of wanting to teach me about each topic. The guy talked about D&D for 20 minutes straight. He starts talking to me about circuits, I tell him I studied electrical and computer engineering, and he still proceeds to try to teach me about circuits.
Around the 2-2.5 hour mark, I feigned being tired and needing to be up early the next day to get out of it. He wanted a detailed description of what I was doing so early the next day. Ironically, that was the most interested he looked towards anything in my life.
Nightmare With Neighbour's Co-Worker
Just before my junior year in HS, our neighbors (upper middle class neighborhood) hit a rough patch and the wife took a second job at McDonald’s. She was kind of a surrogate mom to me and so I’d stop in and say hi every now and then.
One of her co-workers was a Navy guy who decided he needed to go out with me. He was very much NOT my type, but he seemed nice and kept begging my neighbor for my number, so I succumbed to the pressure and said yes.
The evening started by him running late. He called me from a pay phone saying he had a flat tire and asked me if I could help change it. I mention this to my dad and he’s basically like “I’ve got this” and goes to help. They show up an hour or so later and my dad (also a Navy guy) makes it clear that he does NOT like this dude (find out years later that he’d mentioned “her perfect little ass” as a reason for wanting to date me) and sends me off against his better judgment with pepper spray.
Head out to a local Mexican place where he proceeds to eat like an absolute pig, talk with his mouth full, rattle his glass of ice at the servers and curse…well, like a sailor.
I give him a slight pass on the bad manners considering he’s been on a boat for a while, hoping it gets better. It doesn’t.
He takes me to see Mr. Bean and spends the entire movie laughing so obnoxiously that the people a few rows behind us start throwing QUARTERS at us. Not pennies, not popcorn or candy, but actual freaking quarters.!! I expect him to maybe stop, but he doesn’t. In fact, it’s like it isn’t happening at all and it continues. slouch down in my seat and pray the movie ends soon.
He drives me home and insists on walking me to the front door even after I politely decline. We get to the porch and kisses me. This disgusting, gropey, completely unwanted kiss and then says “let’s go inside.”
Just as I’m saying no thanks and reaching for the pepper spray, my dad swings the front door open and says “get within ten miles of my daughter ever again and I will make sure nobody ever finds you.”
Guy ran so fast back to his car he practically rolled downhill. Never heard from him again, thank God.
A Date So Bad, It Actually Sounds FAKE!
I went on a date that seemed to get worse and worse and worse, I honestly felt like I was on a prank show. I’m on mobile and I’m not an excellent storyteller in writing so I apologize in advance. Also this story is LONG.
I met this guy on OKC- fairly handsome dude and he seemed fine. He lived near me in LA but worked in Torrance and wanted me to go to Torrance to meet him during weekdays. This is fine if I have advanced notice- at the time I was working 8 hour work days as a physical therapist and I just started and launched a clothing brand with friends in the SGV and started training for a powerlifting meet (think 3 hour gym days) so I was really, REALLY busy and driving long distances all the time. He asked for my number pretty quick but I just gave it to him because he seemed normal. He chose to go to PFC (super Americanized Chinese food) and I said fine- so I’ll just list the things he did in order because there’s so much:
- Hostess asked where we wanted to sit and he said anywhere and when she sat us he changed his Mind and picked the BIGGEST booth table in the corner, the one shaped like a horseshoe.
- I sat down on one end and scooted in on one side of the horseshoe booth and he was just standing there for three minutes taking off his jacket and sweater and messenger bag off, and put it on the back of the booth behind me, not next to him. He then goes to sit and enter the booth on the other side of the horse shoe but he goes ALL THE WAY AROUND so he’s sitting right next to me, not across or corner/corner, but next to me.
- Wouldn’t let me order what I wanted because he doesn’t eat beef. So I just ordered what he could eat too- chicken lettuce wraps. When it all came, he scooped a tiny spoonful for me on my plate but took ALL the big nice pieces of lettuce leaving me with scraps.
- General rudeness to the waiter throughout the entire meal
- Horrible conversation: he said he makes music which I thought was some topic I could grab onto and explore because he was so boring. So I’m asking what kind of equipment or what kind of music he likes to make- he says that he makes “all kinds of music” which doesn’t make sense to me. Turns out that he meant he makes PLAYLISTS and burns them on a CD. Breh. Then I try to be nice and ask what genre of music and he couldn’t answer that. So I told him to name ONE artist- any artist. Or any song. He couldn’t name one. Also he was overall very whiny about everything- family and his job it was VERY unattractive. He didn’t ask me any questions.
- He would randomly move his face really close to me and go “heellllloooooo” in a high pitched voice throughout the dinner.
- He’d also call me “______bear”. So if my name was Sarah he’d call me Sarahbear. Throughout the ENTIRE date.
- This is the worst: While we’re eating, he asked me if I was a woman. WTF. So I reply, “uhh… you mean was I born a woman? Yes. Do I look like a man to you?” I was certain I wasn’t going to have another date with this guy but i was being nice and tolerant to his weirdness at this point. But this was rude. Also, I’m a thick asian girl but I have no features that are masculine besides my personality lol. So I’m done at this point. He goes on this tangent about how OKC has a lot of trannies that pretend to be women and it’s really hard to tell now, etc. So I told him that even if I were transgendered, that’s not the way you ask people that. He also went on a anti-gay and lesbian rant, even citing that if Russia was a more Christian nation, they would have won the world war. Then he says, “I’m not against gays or lesbians but that is disgusting” and I cut him off just laying it into him- by calling someone disgusting he is definitely against them and all this other bullshit. Now I’m mad.
- I’m done, but I still feel bad for just walking out on a guy. I try to do the mature thing and sit it out and never talk to this mufucker ever again. But he takes his time. He orders tea. Asks for it for free and the waiter does, bless him. Drinks it ALL by himself and doesn’t offer any to me despite having two cups. I’m talking like he’s taking his time and he drained the entire teapot to the last drop.
- I was clearly uncomfortable and it was cold and I was wearing a shirt that showed a little cleavage and would close my sweater because I didn’t want him to see my any more and he told me to just take the sweater off and to not hide myself all the meanwhile looking at my chest. At this point I was no longer nice- I told him I’ll do whatever I want to do and I’m wearing my sweater because it’s cold.
- He kept touching me during the date- my ear, my hair and I told him to please stop touching me. He kept doing it though and when he said all the anti gay stuff I was so pissed so when he did it again I swerved his hand and kind of blocked it and just talked to him like he was a child- “I TOLD you to stop touching me but you keep doing it do you not know what consent is? Do. Not. Touch. Me”
- He then later comments on my legs/thighs and asks if he could touch them/massage them and I told him absolutely not. Don’t. Touch. Me.
- I go to the bathroom and decide whether or not to ditch him but I come back to the table and throw $30 (because I don’t want to owe him anything at all) which is more than enough for my share. He looks at the bill and calculates it and says oh this should cover it- and proceeds to say that he’ll take care of the tax and tip. BITCH I PAID FOR PART OF YOUR FOOD TOO AND YOU ATE ALL OF MINE. I can’t confirm though but I don’t think he tipped my waiter either.
- At the end he wanted to go to a movie but it was too late and a workday and I didn’t want to so i said no. I tried to walk away as fast as I can but he walked me to my car and tried to give me a hug but a side hug and said something along the lines of wanting to give me a side hug because he felt closer to me. Gag.
- I get out of there ASAP, even taking random turns so he doesn’t follow me. The next day I text him something polite- that it’s not going to work because we have such different views of life and beliefs and we shouldn’t see each other again. Then he goes off on me- saying the ways of the world is wicked and G-d (his typing) is not pleased, something about LGBT is a mafia and some other crazy batshit stuff. I just lay it into him, and at this point IDGAF about hurt feelings. I tell him that I absolutely don’t want to date and he says, “that’s okay we can be friends.” I tell him no, and he says we can still talk, and it just goes on and on. He’s delusional. I have the screenshots I should share this shit.
My whole story sounds SO FAKE because there’s so much wrong with it but if you see the texts you’ll realize the rest of the story is completely true.
Sorry for being so wordy, there was a LOT to write. Thanks for getting to the end of you read. Also, he said he was 5’9” on the profile, I’m 5’7” and he was way shorter than me. What a freaking liar.
Double Date With Boyfriend's Friend
So my boyfriend and I went on a double date with his friend and his friends incredibly racist, attention seeking, psycho fiancé. We’ll call her Becky. We went to dinner and then we were going to go back to their house to watch a movie. Everytime a black family walked past us at the restaurant, Becky would say something like “oh wow, look, the father hasn’t left yet!”. My boyfriend and I tried our absolute best to quiet Becky up which just lead to her talking about how PC culture and liberals are taking over freedom of speech. Anyway, we get back to my boyfriend’s friend’s house. Me and Becky went to the basement to set up the movie on the TV while my boyfriend and his friend were upstairs, I forgot what they were doing. Becky opened up a two liter bottle of soda and spilled it everywhere on a nice carpet. My boyfriend’s friend asked Becky to clean it up which made Becky say “what am I, a dog? You’re talking to me and commanding me like a dog!”. Lots of yelling went on over spilt soda while I ended up cleaning it. Becky walks out the door and I go after her. Becky is hiding behind a tree and peering over to see if her fiancé will chase after her. He comes out and they fight some more, she throws the engagement ring into the street. All over spilt soda.
Ex-Girlfriend Shows up With A New Man During Date.
Went on a date with a guy who insisted we have dinner at his favourite steak house.
We ordered our food (I noticed he ordered the most expensive meal on the menu) and I suffered through boring conversation with him.
Suddenly, his ex-girlfriend walked in with her new man and the two of them were shown to their table. They didn’t see us but my date saw them and he broke down crying. They split up 4 months prior but he was a mess. Our date suddenly turned into some kind of awkward therapy session where he sobbed about how much she broke his heart.
Our cheque came and my date said he left his wallet in the car. My eyes widened and he said “No, nothing like that! Don’t worry, I’m not gonna bail on you, you’ve been so good to talk to. I promise I’ll be right back.”
He never came back. I had to pay for our $120 dinner and walk out alone.
A Date Who Probably Showed Up For Free Food.
Went out for a date with a girl who didn’t understand what conversation was
Keep in mind, I have Asperger’s so I’m not great at conversation to begin with
Me: “So what do you want to be when you’re older”
Me: “Oh cool, why’s that?”
Her: (With a tone as if it should be obvious and I’m an idiot for asking) “Because I want to be one…”
Me: “Yea, but what got you into law in the first place? Do you want to help people, or get loads of money, etc.”
This was basically the entire date. Me bringing up different topics and her basically refusing to answer any question with more than a single word answer.
It was as if she was trying to make awkward silences on purpose.
When the bill came she just said “Can you pay?” I mean I was gonna offer to pay for the bill anyway but it’s a bit rude to just ask like that
So I paid, drove her home, and she got out of my car in complete silence. I said goodbye and she completely blanked me
Either she was a complete psychopath or she wanted a free dinner. Seriously though, her meal was only like £8 I think. Why would anyone sit through hours of that to get a free £8 dinner.
Co-Worker's Creepy Nephew.
Set up on a blind date with a co-workers nephew. I was around 19 at the time, and according to her we’d “really hit it off.” Fast forward to the date, he brags half the time about his gun collection and entire family’s redneck traditions and gun-toting heritage. Literally looked like his family could be on a Jeff Foxworthy TV Special. Good for you, but not my kind of thing. Other half of the date he thought it would be a good idea to list off all his illnesses/disorders. Seriously. Full list, including the family history of diabetes, muscular dystrophy, M.S., developmental issues they’ve all had, etc. Who the heck reads off their medical history on a first date?! A blind first date?! You’re trying to attract someone, aren’t you?? Needless to say, I haven’t agreed to blind dates since then.
Date With A DJ Gone Wrong.
Let’s set the stage: I was Nineteen, a Freshman in college and had a boyfriend who was still a Senior in high school.
I was reconnected with a long lost elementary school friend who happened to be in my religion 101 class. She had gotten my name on some list to enter a club that weekend, underage, but hey, it’s cool……….looking back on it all, she may have been working as some sort of escort during her college years, but I digress.
I had a few, and started dancing. The DJ noticed, and struck up a convo. Honestly, he probably isn’t what you are picturing. He wasn’t some slick looking club DJ, he was a regular looking white dude with super long hair in a low ponytail. He was 29, which was essentially ancient to my 19 year old mind. He asked me if I wanted to hang out sometime. He seemed nice, I accepted and gave him my digits.
I know what you are thinking, ‘What about your high school boyfriend?’…Well, in my naivete I had accepted this invitation with the Dj with zero intent of it becoming romantic. I thought he was nice, I was a kid, I was in college, I should have not stayed with my high school boyfriend for that time period, and I was just like, living my life. Believe me, it barely reflects who I am as a person.
DJ picks me up from my apartment, and since I am 19 I suggest we head back to the club of our meeting. Known for letting in underaged chicks, oh god.
I start slamming drinks, even though they almost always make me sick. He buys, I slam. I tell him I have a boyfriend, making it clear that this is not a date.
I start to feel sick after being out for about 45 minutes. He offers to drive me home. We pull over twice on the drive home so I can puke on the side of the road. He drops me off, I puke once more and head inside.
He did send me one text after that. It read, ‘I hope you are enjoying this beautiful day. You are beautiful’. I was like dude, I am a kid who puked all over your night and took you on a weird, platonic trip.
This was a story about the DJ’s worst date. It was all me.
Date With A Guy Who Looked Like My Dad!
I was set up on a blind date with a guy who looked like my dad. The whole date was a train wreck so that was just icing on the cake. Here’s what happened:
It started off with me accidentally being an asshole and semi standing him up. I was in a concert that went on way longer than I expected so I missed the start of our date by like an hour and a half. We were texting though (during the concert but I was at the very back and no one was near me) so once I managed to describe where I was (didn’t know the name of the hall), I convinced him to sneak in. He was stopped by security immediately.
Eventually we did meet up in a Tim Hortons near his place. This is where I learned of a massive difference in expectations between us. You see, I thought we were on a date. He, on the other hand, had an interesting interpretation of my previously laid out boundary: needing-to-get-to-know-people-before-going-intimate.. Without ordering anything, he sat down and said, “What do you want to know?” He had no interest in getting to know me at all, he just wanted me to fulfill the minimum requirement of knowing him so that I would have sex with him that night.
Towards the end of the evening, when he realized that maybe I wasn’t going to let him have sex with me in exchange for basic facts about him, he started reviewing my reasons for not wanting to go home with him and tried to counter them logically.
Once this inevitably failed, he tried to guilt trip me because I “stood him up” at the beginning of the evening.
All the while I could barely look at him without laughing because of the striking resemblance he bore to my own father. Needless to say, this was not a great night for either of us.
First Date After Break-Up Turns Out To Be Horrible
Long story… My boyfriend and I bad broken up and I was heartbroken. My boss decided that she should set me up with a nice and rich man. I think what’s the harm. I haven’t been on a first date in years at this point and I didn’t know what to do. I brought a few dresses to work to figure out what to wear that night and put a lot of effort in to looking nice. I was living with my boyfriend before we broke up so I was back at my mom’s house until I arranged another living situation. I also went to rehab in 2011 (it was probably 2014 at the time of this story) so I don’t drink and I told the guy that. I also told him to pick me up from my mom’s house. He shows up in an uber (which freaked my mom out because there were 2 guys in the car) he did this because he had done a couple of shots of vodka because he was nervous. Also he was wearing a track suit. Great start! We get to the restaurant that I thought we were eating at and it turns out that he didn’t make reservations because he “knew the owner” unfortunately it was December and the entire restaurant was rented out by a company for an office Christmas party. So he gets another uber and we try to find somewhere else to eat. He stops the uber randomly and then we walk like 6 blocks in the cold (he is walking very fast so I am basically running in heels to keep up with him). He asks if I like seafood and I say no. He decided that an oyster bar was where we were going to eat. Awesome! I am very good at holding a conversation. This guy was not. Every time I would ask something to get the conversation started he would throw in a conversation stopper. I started to run out of topics. He kept asking me if I was bored which was very awkward. He also eats like a stereotypical girl and basically just pushed his food around on his plate which is always weird. While we are at this restaurant he has the equivalent of 2 bottles of wine. Again I am not drinking. We get to the point of dessert and he got banana pudding or something and since he can’t hold a conversation I start spewing off random facts about bananas and banana trees which was weird. I usually don’t give out banana knowledge until at least date 5. After we are done he asks me if I want to go to a cool bar “it has a great atmosphere” I tell him again that I don’t drink but if he wants a night cap then we can go. So we walk/jog to this bar and it was really cool. It was getting late-ish and since I was living with my mom I wanted to be respectful and get home at a reasonable time as to not worry her (again I was enough trouble to go to rehab so it was the least I could do). We didn’t really talk at all at this bar because it was kind of loud and he can’t hold a conversation to save his life. I tell him that I have to get up for work early in the morning and that I’m living with my mom so I needed to get home soon. He started talking about how my mom was a hardass which is a big no for me. Don’t talk about my mother she went through hell for me and still loves me. I tell him that was not okay and that I needed to go home. He said he would get an uber. So I patiently wait for the uber to arrive and he walks me to the uber (I assume that he is getting in it at this point so I open the back door) and he says that he is going to stay but that he will pay for my uber home. He gives me a hug and we part ways. I get in the front seat of the uber and as we start driving I start hysterically laughing and telling the uber driver who is old enough to be my dad about the horrible date I just went on and we laughed the whole way to my house. When I got home I received a text from this guy that said I had a really great time and I’m sorry if you were bored. I tell my mom about this date and we stay up laughing about it for the next hour. I told my boss the next day that it was horrific, but that I appreciated her trying. I will never forget this date even though I cannot for the life of me remember that guys name.
Matrimonial Service sets Up A Disaster Date.
I was 18 and my mother signed me up for a matchmaking service. This was 1996, and she thought I should be married or something already. Anyway they set me up with this dude and we agreed to meet at a local burger place. I got there and went in, and things were ok. Decided we should go to a movie , and since things were going ok I rode with him. BAD MOVE!!!
We get in his car and on the ride there, he’s trying to sell me his Christian music CD. Told him I was not interested, he started playing it and he can’t sing at all…but his sales pitch didn’t stop. I was miserable. He kept going on about his love of God and Jesus, it was frightening the way he spoke about it.
Get to the movies and he doesn’t have money, so I buy tickets and we go in. It’s some comedy with Jim Carrey. Previews start and he looks at me and says “You know “local meteorologist” ? “Well, I cast 2 homosexual demons out of him last week. Then I cast 6 out of my sister”. and turns around to the screen. I. Am. Terrified!
I spent the next half hour trying to figure out what to do, this is something I’ve never encountered and sheltered me doesn’t want to hurt feelings. His laugh was terrifying, and I got some balls and left for the “restroom”.
Bolted, called my mom on the first payphone I saw and never looked back. I called the dating agency the next morning and they said he had red flags on his record to never be set up with anyone normal and they apologized.
He Had No Clue She Was Terrified Of Horror Movies
So I (M) had just turned 16, so I had not taken my drivers test yet. This girl in my friend group who I had a huge crush on, (also 16, had her license) and I were talking about movies, and I asked her if she had seen the new IT movie yet. I had already seen it, and thought it was really good, so when she told me that she hasn’t seen it, I suggested that we go see it together. She said yes! For the rest of the day that was the only thing I could think about. “Did I just ask this girl out?” “This is a date?!” “Does she think it’s a date, or just seeing IT with a friend?!” The next day, we met up at the theater, I gave her a hug. I couldn’t stop smiling and blushing the whole time, wondering if this was the start of a potential relationship or not! We flirted a lot in the past, but never did anything just the two of us without the friend group! She told me that she doesn’t like scary movies, and she would feel better if we held hands, the butterflies in my stomach turned into goddamn pterodactyls, that’s the only way to describe it. I told her that the movie isn’t really very scary at all, and I don’t like horror either. AAAAANYWAYYYYYYYY. She REALLY does not like horror movies. She was gripping my hand like a vice, we only made it a quarter of the way through the movie before she told me that she can’t watch it anymore and she was going to call her dad to pick her up. (She had her license but no car yet, and I had neither). We left the theatre, and as were waiting, my mind is just racing, wondering what the hell I did wrong, could she actually be that scared of this movie, or does she want to get out of this situation? Her dad arrived, and she asked him to drive me home… that was the most awkward car ride of my life. Her dad trying to make small talk, while me and her are just sitting in the back seat…
Bet you’re wondering what happened after that awful first date. We just celebrated our 1 year anniversary in October! That’s another story on its own, maybe I’ll tell that one later. It’s not as cringey as the last one I promise, it was really fun.
Fractured A Foot While On A Tinder Date
I had a tinder date. I had a huge night the night before and was severely hung over, but he had called to check if we were still going, so couldn’t bail.
We were to go to Bounce with a few people that were on holidays staying at his place. He asks me to pick him up, which I do.
We get to Bounce and all is well, he goes to the bathroom and I’m on this long jump type trampoline that you jump into a pit.. well, I ended up fracturing my foot in 4 places.
He finds me, and I say I need to go to hospital, he drives my car, and that’s where I learn he’s actually lost his license
We get to the emergency room where I wait around for X-rays and all that, he eventually goes off to find food and I keep him updated on what’s happening.
While I’m waiting, my ex’s sister is also sitting in the emergency room (as if that could make the day worse)
Basically, he stops messaging back, I’ve been bailed on, I can definitely not drive my manual car back home and manage to get 2 mates to pick me and my car up
Forced To Meet His Mother On First (Disaster) Date
I show up at a thai restaurant for a date with a guy I met online. When I arrive he’s waiting at the bar. We grab a seat and order, then he asks to for me to go outside with him so he can smoke a cigarette. Once we get outside he starts complaining how he doesn’t want to eat there and we should leave. At this point it’s apparent to me he’s had a few drinks so I try and roll with it. I agree but tell him he needs to at least go back in to pay for the drinks and let them know so they don’t put our order in. A few minutes later he comes out with the waiter yelling at him as he’s leaving. We decide to walk around downtown and a tourist (obviously middle eastern, traditional clothes and all) asks for the time (in English) . He takes this as an opportunity to show off his Spanish speaking skills. We sit down at a bench at which point I’m realizing he’s had more than a few drinks and is slurring his words asking me to kiss him. I explained he pretty much ruined his chances of a Goodnight kiss. I tell him I will drive him home. On the way he confesses to me me went to jail for pulling a gun on someone when he was drunk but only shot the gun up in the air so felt was the one wronged in the end. I ask how often he drinks which is getting angry with me so I drop it. We get to his house and his mother is outside when we pull up (he’s 30 mind you) , he insists I meet her, practically dragging me out of the car. I do and politely try and leave, he relentlessly tried getting me to his room the whole time with his mother right there with a sympathetic look that tells me this is nothing out of the normal. I walked out with him still slurring and stumbling behind me, went home and never called again.
Date's Girlfriend Video Calls Mid-Date
I wouldn’t exactly consider this one a date per say but it was probably the worst first impression of a guy I had.
So this guy and I talked on Instagram for a bit. He invited me to an after party at a nightclub with his friends for our first encounter and of course I accepted.
I was already at a party so he was supposed to pick me up at around 3AM at that party so we could go to the night club together. He arrived on time in a nice car, was really handsome and smelled good. We start driving and I notice his iPhone vibrating a few times but he doesn’t answer. After about five calls I tell him to answer the phone to which he answers : “okay but shut up”. I was confused until I heard him pick up the phone by saying “no sweetheart I’m on my own, I swear”. He keeps talking to what I understand is his girlfriend to try and convince her that he was not sitting with a girl in his car. I was infuriated.
They hung up. None of us talked for what seemed to be an eternity and his phone rang again. This time she was calling him on FaceTime. Guess what he did ? He asked me to get out of the car and walk and that he’d pick me a few meters later.
I got out of the car and found myself in an extremely busy street or Paris known for its prostitution, strip clubs and sex shops (if you know Paris, I’m talking about Pigalle). I didn’t want to just stand there and be mistaken for a prostitute so I walked in my short dress, fur coat and heels. While I was walking I could feel the eyes on me, a man even asked me how much it was to spend some time with me. I was really really freaking out at this point and did not feel safe. I wanted to call an Uber but didn’t feel like standing in the street on my own and wait for it. So I walked, heard many nasty comments and finally found a café that was still open to hide there and wait in peace. I was literally shaking when I got there.
While I’m seated there he calls and ask me where I am. I tell him the name of the place and he has the audacity to tell me “why did you walk that far” I was fuming.
When he arrived, I jumped in his car and asked him to drive me home and he proceeded to fall me that I was acting weird. lol. I didn’t answer, and kept quiet most of the ride. He on the other hand couldn’t shut up on how he was going to leave her soon and blah blah blah.
I finally got home. He told me that he didn’t like girls who wear hair extensions (as if I asked him his advice on my hair choice) and that he was looking forward for us to do something together.
I blocked him everywhere and I’m still pissed.
The Guy Who Puked
A bit of backstory prior to this event – I’ve had a best friend (girl) throughout highschool and there always was this unspoken thing between us. We just never clicked at the same time so it was either me crushing on her or she liking me without reciprocation. It’s fair enough to say that I was head over heels fallen for this chick in the last 2 years of highschool, whereas she took me as a friend (I know, the ol’ Friendzone). Nevertheless we kept hanging out, going downtown after school and in general just enjoying each others company.
For the horny, hormone driven youngster I used to be, the time we spent together was usually the highlight of the week and the rest of the time just silent down-spiral of suffering and borderline depression thinking how she spent her time with various boyfriends.
Fast forward to the beginning of summer prior to our last highschool year. I was so lonely and emotionally devastated that I decided to quit our friendship and not be miserable anymore. The plan was also perfect in its simplicity – go out for coffee, like we usually did, and then casually suggest that it’s bothering me that there’s no future between us. I imagined beforehand how ‘cool’ i’d play it and come out maybe even happier… Well you know what they say – Man plans, God laughs…
So there we are sitting in Starbucks (I know – cliche) in a fairly big mall on the 2nd floor. I get it over with and she starts crying saying how I’m an asshole and I shouldn’t even think about apologizing afterwards. I should also mention that I ordered green tea and sometimes my stomach just turns upside down from it. So there I am, feeling really bad because I’ve hurt her, when suddenly I notice the familiar feeling in my gut. And of course, as clockwork, within 5 seconds I start to regurgitate on the table and partially on her. I sprinted out of that place, but it still kept coming so I went over the handles and projectiled all my despair and shame over the 1st floor walkers.
I have no idea what was worse, me feeling incredibly sick and guilty or having to look at her face full of sadness and horror at the same time.
EDIT: I forgot to mention that I left all my stuff including phone and wallet on the table (now covered in puke) and just ran. Worst part is, she had to go looking for me throughout this mall to make sure I don’t need to go to hospital and to give me my stuff back.
EDIT 2: I’m not sure, but I think she was so decent that she never told anyone about it. We patched things up during the senior year and parted ways as good old friends at graduation.
P.S I know this doesn’t really count as a date since we were friends but it’s something I’ll never forget
Date With Pilot Ends In Surgery
He’s a pilot/aerial photographer. It wasn’t our first date – more like our sixth, I think. He flew me to Chicago in his plane so I could tag along to one of his job sites. We had to stay overnight, so we fully expected to be intimate with each other.
We had landed and he got the groundwork photography done, so we decided to put our stuff in the hotel and grab a bite to eat.
We had a great time and left the restaurant after dinner. We were crossing the street and I tripped over the curb. Felt an intense pain in my right foot and couldn’t walk on it at all. He carried me all the way back to the hotel. I REFUSED to ruin this fun overnight date with a trip to a hospital in a different state from where we lived, and I didn’t want to interfere with his work.
I was pissed, thinking I ruined the mood of the evening. He cared more about me resting, constantly offering to drive me to the hospital and checking to make sure I was okay. Obviously, no intimacy ensued, and I felt like such a turd because of this.
I walked on it for 3-4 more days before seeing a doctor once we got back to our home state. I even insisted on helping him carry his gear during the overnight trip so I wouldn’t look like a little bitch (he felt so bad, I didn’t want to make him feel worse).
Once I saw a doctor, they told me that I had broken my fifth metatarsal bone in my right foot and needed surgery to fix it. We were both in shock. I had the surgery and my foot is fine now.
Pizza Date Ruined
My first date with my now wife was going to be incredible. I had arranged with my former boss that we would have his pizza place to ourselves. We would come in just after closing, I’d teach her how to toss pizzas and we’d make a couple small pies to share with a few of our favorite ingredients. Then we would sit in the empty restaurant for a few hours before cleaning up and leaving. Well, he forgot that this had been arranged, and forgot to tell the manager that was closing that night. So we walk in the back, and there’s two guys cleaning up. We ended up making the pizza while holding awkward conversations with them until my old boss showed up and asked what the plan was for the rest of the evening. I couldn’t say “well we had talked about me having the place to ourselves, but that’s not going to happen is it?” so I panicked and said we’d go back to my place and watch a movie, which didn’t go over well as a response. We ended up eating it on a Greenway path under a blanket and looking up at the stars. It wasn’t an absolute disaster, but definitely was not quite how I had envisioned it.
Sweet Revenge On Rude Date
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, yeah… I, um 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.
The Not-So-Perfect Golf Date
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 230 yards 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 if 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 two holes with maybe exchanging 10 words. Didn’t hear from her again.
Pranked By The Restaurant Manager During Blind Date
For this date, I suggested we go to a local restaurant that I frequented. The manager and staff knew me, and they knew it was a blind date.
A few minutes after the waitress got our drink orders, she came back out to our table.
With a pained and serious look on her face, she said ‘The manager wanted me to tell you that you left your prescription for [Insert Name of Gonorrhea Medicine] here last night. Want me to go get it for you?’
It took me a second to realize what the manager, my friend, was doing and I was shocked —because I didn’t have that problem or a prescription for it.
My date just stared at me like a surprised owl.
I finally was able to pick my jaw up off the floor — just as the manager came out of the kitchen, laughing as hard as he could. The waitress apologized profusely, saying that he told her if she didn’t play along, she’d get fired.
Date With Gold-Digger
I get there, she’s already eating appetizers (I’m 10 minutes early), then she orders the most expensive dinner on the menu, and tells me she did it because she knows I’m paying. Small talk fails and for 45 minutes she complains about how no one is refilling her wine glass (she kills the glass every 20 seconds).
“She mentions how she was told that I make a decent salary, multiple times. I try to be civil and change the subject. Awkward conversational topics ensue, nothing even close to first date etiquette follows. Three quarters of the way through I go to the bathroom and our waiter walks by, asks me if we are doing a reality show or something along those lines, since he has seen this disaster in motion.
“We talk about how wild this woman is for about five minutes and then I ask him to stop at our table and ask about the bill. I immediately say split checks and give him $80 (roughly 40 for my bill and 40 for his tip). The date looked shocked and ended up not being able to pay her bill, so the friend who hooked us up got a call and flipped the rest of her check. Her total came to be about $75
Tinder Date Gone Wrong
I met up with a guy at a bar. It was like pulling teeth to talk with him. I try to talk about travel — ‘I don’t see why anyone would ever want to leave the US.’ I try to talk about running — ‘I don’t know why people run for fun.’ Finally he contributes something as says he likes cars. So I tell him about how my brother just purchased an Aston Martin.
‘Aston Martins are shit. I really only like Camaros.’ I tell him I drove an old Camaro for nine years — ‘You don’t know s— about cars.’ (I don’t, not going to deny that…but really, all I said was that I drove a Camaro from age 16-25).
By the time I get home, he has deleted me from Tinder.
Weird Date With A Toxic Misogynist Man
One guy casually told me that women need to be escorted to the grocery store so that they ‘keep their eye on the prize’ and ‘don’t spend like $200 on random things’ (his actual words). Then he proceeded to explain why he was right about this and why it’s not offensive when I told him that I did not appreciate his statement.
Then he told me about his years of psychological and physical abuse by his father, eventually culminating in him being stabbed by his father.
He also suggested I listen to a couple of his favorite podcasts by a Trump-supporting, feminist-hating misogynist.
On the way home (I gave him a ride because it was cold out and I’m apparently a bleeding heart) he asked me if I would go on a 14-hour road trip that weekend with him (which would have been our second date by the way). Hard no. Like…were you on the date we just had?”
Date Introduces Me To Her Husband.
I had been texting this girl for a good three weeks, and we finally decided to go out on a date. I suggest we go to dinner and a movie at an Italian restaurant closer to her place so she can walk/bus, and I can do all the commuting. It takes me an hour to drive there, and I arrive at the restaurant before she does a good thirty minutes before our date, so I could be prepared. The waitress brings her to my table, and I see another man walking with her. They both sit down and at this point I’m really confused. She introduces me to her husband, and he tells me that they’ve been looking for another man to join them because his wife likes sleeping with two men at the same time, and he’s into it as well. For the first time in my entire life, I was completely speechless. I had no idea how to reply, so I just got up and walked out of the restaurant without saying a word.
"Inetellectual" Date Turns Out To Be Clingy
The Starbucks date didn’t start off terribly—he was about 5 inches shorter than he’d claimed to be, but was also WAY cuter than his profile photo, so I felt like it all balanced out. (And to be clear: his actual height is a non-issue; lying about it was the downside.) But when we actually started talking, I felt like all this dude wanted to do was prove how ~*intellectual*~ and different he was. Strike one: He said he preferred to spend his money on experiences rather than things. I agreed, and started talking about my love of travel—at which point, he interrupted me to say I probably “still owned Uggs though”… and then he LOOKED AT MY SHOES TO SEE IF HE WAS RIGHT. At that point, I realized I didn’t need to wait for three strikes. I immediately came up with an exit plan: I needed to pick up a gift for my niece at Sephora. He followed me to the store, sharing his thoughts on makeup and opinions on girls who wear too much of it all the way. We did not go on a second date.
Crazy Date That Went MoreLike An Interview
After online dating for a while, I was so over exchanging endless text messages before actually making plans for a first date. Instead, if a dude seemed to have decent spelling and a job, I was down to meet up and decide in-person if there was something there. I set up one such first date at the pub down the street from my house. In the hour leading up to the date, my phone would not. stop. buzzing. “I’m driving to the subway station,” my date wrote. Fifteen minutes later: “I’m getting on the subway.” Twenty minutes later: “I’m getting off the station.” Two minutes later: “I’m walking up the street.” Cool story bro, just get here.
And then he did—wearing grey sweatpants and a Bob Marley t-shirt. We sat down in a booth and he immediately starting talking about everything from his childhood to his job. I started ordering doubles. Clear that this wasn’t going to be a two-way conversation, I went into interview mode. He mentioned that he was an inventor at heart, and that one day, he was going to be so successful that he would be in a photo with the then-U.S. president Barack Obama, pointing at his new bud and saying, “Yeahhh, this guy!”
OK, so what are some ideas you have for inventions? I asked. He proceeded to tell me about how he wanted to revolutionize the typical kitchen, constructing a wall with a variety of different sized slots in it. Each slot corresponds to a particular type of plate or bowl (Note: the related dishes had to be bought separately from the kitchen reno, but as he explained, that would be a “one-time purchase”). After eating on these dishes, the user would put it into the appropriate slot where it would go into the wall, get washed, dried and put away. And he called it the “T-Wash” because his name was Trevor. THIS IS A DISHWASHER BUT SO, SO MUCH WORSE.
When T-Wash, as he has now become known, got up to go to the bathroom, I texted my friends to tell them the date was a dud. They agreed to meet me at the subway station and when T came back, I informed him that I had to get going. “Well, this was fun, when can I see you again?” he said. “Um, thanks but never?” I responded, trying to catch our server’s eye (I wasn’t about to stick him with the bill for my drinks after a short AF date that ended with me bailing). For some reason, even though we were basically the only ones in the bar, the server took her sweet time coming over to us and as a result, I had to sit there and, at T’s request, explain why I wasn’t down for date numero dos. (Fun fact: It turns out that he changed from his work clothes into sweatpants because I “seemed like an easy-going chick.”)
As soon as my debit payment went through, I waved goodbye and booked it out of the bar. It was only when I was recounting this story to my friends later that night that we realized, T was stoned the entire time.
Mass Texter Caught Red Handed
There was a guy I never even actually met, because I got a super creepy vibe from him. He would send out mass texts, regularly, asking if I wanted to do anything that night. I could tell it was a mass text… because it showed the numbers of everybody else he was texting… on my iPhone. Conversation, after many ignored texts, as follows.
Him: Hey, want to do anything tonight?
Me: Can you please remove me from this mass text list?
I’ve never even met you.
Him: This isn’t a mass text lol.
Me: (Screenshot where it lists everybody else he’s texting)
Him: Oh lol. You caught me.
Random Stranger: Yeah we can all read this.
Me: Yeah bye.
Creepy, Weird, Awkward And Embarrassing Experiences
These redditors shared their gruesome experience which ironically, would stay in their memory forever.
Sure we all have a bad dates and weird experiences, doesn’t mean we stop. Go out, meet new people and make new memories
And share your experiences in the comment section below.