15 People Share Their Most Awkward, Disastrous Dating Fails

Dating isn't easy... but these particular people had some of the worst dating experiences ever!

The Wasabi Disaster

“I had my first date ever in 9th grade all planned out with a girl I really liked. When I was running through the plan with my friends, they reminded me how socially awkward I was and that if I couldn’t carry the conversation throughout the date, there wouldn’t be a second one. So me being the smooth guy that I am, I decide to prepare by googling ‘How to talk to a girl’ and ‘Conversation starters’ an hour or so before the date. but I was too nervous to memorize the questions, so I wrote them down on my palm for future reference.

We went to a sushi place at her suggestion. Of course I say I love sushi to convince her I am a sophisticated and worldly gentleman, but I’d never had the stuff before. Turns out that green substance they put on the side of the sushi roll is not, in fact guacamole, it is wasabi sauce which I can only describe as a combination of horseradish, fire and hell. I ate the whole chunk of it and there I am, practically sobbing and oozing mucus out of my nose when I decide to distract her with a tactical conversation starter. Only problem is, my palms were too sweaty and all the ink had bled. I didn’t notice while I was wiping the wasabi-induced snot storm off my face, so now my face was covered in bled ink and snot while she stared blankly at me wondering what to do. I saw myself in the reflection of window and I was in so much pain and so mortified that I just started crying. We ended up having to call my mom to pick us up early (shut up, I was in 9th grade) and drove home in silence except for the oldies station my mom had playing on the radio. My mom let me use her sweater to wipe my face off. We ended up being friends later on in high school and laugh about it now. To this day, she thinks I was only crying from the wasabi.”

(Source)

What’s The Deal With This Guy

“I went out with a guy who wore the puffy shirt from Seinfeld. I swear this was the same shirt. I looked beyond that, or at least tried to, and continued with the date. He later had a meltdown in his car because I said hello to a male friend we had seen while we were at a coffee shop and laughed when he told a story to me. He said my laugh was sexual towards him and that he shouldn’t have ‘fallen for me’ so quickly and wouldn’t have if he’d known I’d ‘cheat on him so fast.’ He was crying really hard the whole way back to my house. it was the most awkward car ride home ever. We never talked again.”

(Source)

Baby Talk

“My good friend, Vicki and her husband Will are always trying to set me up. I usually turn down their offers, but they talked up this guy, Ben. He seemed like a great guy, smart, a doctor, and his TMNT collection was bigger than mine! He took me to a pretty nice place for dinner, and I was kinda nervous but nothing like, bad. And THEN he spilled his drink–on purpose! I saw it! So, I was like What? And then he started talking like a baby!!! ‘Ooopsie, I spwilled mwy dwink….I’ma bwad boyyy….’ And I was like, ‘Ben? Are you ok?’ And he kept at it, baby talk, looking all coy…and then he asked if ‘Mommy wanted to spank her bad boy’…. I was outta there! I just got up from the table and walked out. He ran after, talking normally, apologizing. I had to wait for my coat at coat check. I accepted his apology, assured him I wouldn’t tell Vicky and Will about his kink. And then he went to hug me, and it lasted a little too long…I pushed him away and …well, there’s no polite way of saying it..he ‘jizzed’ in his pants. I like have no PROOF, but yeah, he did. Against my leg. I ran away. So, yeah, WORST date EVER.”

(Source)

Reddit Addict

“I went on a date with a Redditor. We met up, got dinner, saw a movie, and went back to my place to just hang out and chat. Long story short, he got on my computer, got on Reddit, and one awkward hour later, I drove him home. Y’all, if you aren’t impressed with a date, just let them know. Don’t Reddit at their house awkwardly and act really weird. No bueno.”

(Source)

Not What He Expected

“I let a friend set me up on a blind date. She told me this girl was a reasonably attractive brunette who was witty and funny and very honest and outgoing. I don’t like blind dates but this friend loves to match-make and was sure we would be the best couple ever! Fast forward to date-day. I am pretty optimistic. I phone her and we agree to meet at a Buffalo Wild Wings for a few drinks and some food on a Thursday night (all good signs of things I can get behind!). I agree to meet her at 8pm. I arrive about 7:50 and text her I have arrived and I grab a table since it’s busy. She responds that she is on the way. 8pm, she’s not on time. 8:15, still nothing, I order a beer. 8:25, still nothing. This waitress is flirty and fun though. I order an appetizer. 8:35, still nothing so I start eating the appetizer. Beer #2 arrives. 8:45 She still hasn’t showed up, no call and no text from her and it looks like I am going to be stood up. I should have left 30 minutes before but I wanted to not be a stuck up douche and give up on a good friend of one of my best gal pals.

Finally 8:50 comes and the girl arrives and holy cow was I in for a surprise! This photo of an athletically built brunette weighing about 120 and standing 5’6″ couldn’t be any more radically wrong. I’m guessing the photo I was shown was her at like 18 or 19, or a senior picture from high school… She has fiery red, curly hair (with obviously brunette roots) and about 100 pounds over her photo comes over to the table and introduced herself and she says she is sorry she is late and nothing else. We proceed to have the most awkward 45 minute BWW experience I’ve ever had. She had terrible body language, awful eye contact….oh and she was ‘witty and funny’ alright. In that way that people say ‘HAHA I AM SOO FUNNY!! AREN’T I QUIRKY AND ADORABLE!?!?!?’ Yeah, she was one of those. Annoying as fuck. Vapid as fuck. About as deep as a toothpaste cap. She pretended her honesty was intelligence, and it definitely wasn’t. I’d never been more turned off… So after 45 minutes, we finished out dinner and packed up and went our separate ways. But that lovely waitress came back over and expressed she was happy that I didn’t get stood up and I let her know a good friend set me up and I told her I would have left if she hadn’t been there to keep me company! Got her digits, she’s still my girlfriend.”

(Source)

What A Day

“Oh boy. Well, I was about 18 and working in the city (New York) at my father’s printing shop. I had met this guy a few days before on a bus going up state to visit my friend. I tell my father I’m leaving early to go hang out in the city with a friend and I’m just gonna take the train home from there. I meet up with the guy, and almost immediately he’s weird. Think Pepe Le Pew. Like he’s trying to get all touchy feely and huggy squeezy on the subway. Then he pulls out a disposable camera and asks if he can take my picture and tell people I’m his girlfriend. I of course say no, but I was a big people pleaser and didn’t want to hurt his feelings so I didn’t end the date, but I couldn’t wait to get away. This continued until we were walking down some random street and some woman comes up to me and starts getting in my face. It was his girlfriend! I shit you not, we’re in fucking Midtown Manhattan, and we just happened to pass her by hanging out with friends. I tell her to get out of my face because I had no idea he had a girlfriend and am actually relieved she decided to show up. He starts to follow me and I just turn around and say, ‘Dude, you really don’t want to do that. TRUST me.’ Since my train wasn’t for a while I decide to go back to the office to wait. When I got there I found my father cheating on my mother with the woman he hired to help with the filing.”

(Source)

Oh The Drama

“I was at a party once, and got approached by a girl. She wanted to set up a double date with me and my buddy- and her and her friend. My friend and I accepted. The day of the date, the friend cancelled on my buddy, which was probably because it was just a setup for me and girl A in the first place. Ok! Sure, we go on. So we set up a movie, and go see it. After the movie, she wanted to go back to her dorm / apartment complex and hang out with her pals. The date was going ok, so I agreed (It wasn’t odd, college age, I was 20 or so, I think she was 22). So we hang with her roomies for a while, things are ok, then they want to go out, so they leave. I offer to leave, like a normal gentleman, and she indicates I should stay for a little. I agree.

We put on another movie, and I make a move to kiss her, and we kiss for a minute or so……….then………suddenly….. She pulls away without warning and immediately gets really agitated. She wants to know where things are going, and before I can answer she begins crying very, very hard. She goes off on a tangent for about an hour about all these very odd issues she’s having and how nothing is right and all men are going to abuse her (wtf?) and so on. Now within the first minute of the freak out I’m thinking, ‘Ok, this is over. Let’s find an exit strategy, this girl is obviously not ready for anything.’ But this was a mistake: Because I start asking questions, out of morbid curiosity. As it turns out, I’m like the second person she’s ever kissed and she’s a virgin, because her mother was super overbearing and never let her date, and told her all men were going to kill/abuse her and leave her in a dumpster. She thinks because I kissed her that we have to have sex now, but first she wants to call my parents and make sure I’m not an axe murderer. Can she do a background check on me and see my grades? Oh now wait it’s back to the sex subject and she says she wants to but she’s afraid and doesn’t know what to do, and so at this point I stop her. I tell her that I’ve had a few girlfriends in my time, and that she’s better off finding someone a little less experienced, since she’s not. I tell her I’m not interested in sex right now, nor a relationship (well I totally was on both parts, but not with crazy people). I tell her the connection between us was good it’s just not right for us to sleep together.

She cries really hard again, but agrees that it’s not the right time, not the right person, etc. I go home, chalk it up to a bad night. Now, mind you, all this girl had was my name, and telephone number. I think she had the telephone number of my friend. The next morning, at 7:00 A.M. or so, I get a knock on my door. I don’t live on campus, I live waaaay off campus with roommates. It’s her. Now I’m freaking, because how did she find my house!!!! She’s got flowers, with a card. She’s still crying, and she apologizes for her behavior the night before, and wants me to wait to read the card until after she leaves. I agree, and she tearfully walks away. I go inside. The card says (I’m paraphrasing of course) ‘I really like you, I know I probably scared you away, but if you ever want to give it a shot, give me a call.’ Right about the time I think, ‘Well, maybe someday…’ an INTENSELY loud pounding starts on the front door. I answer, it’s her, she’s SCREAMING and in tears. I ask why, and she’s livid at me for not reading the note and chasing after her. Now I’m thinking WTF x ten to the millionth exponent. But I calmly explain I need some time to think about it, especially since she just started trying to break down my door. She falls on the floor crying. I attempt to console her, and she flails at me and cries harder. I wait for like ten minutes for her to stop crying, and she agrees to give me some time. She walks away again.

It’s not 30 seconds before the pounding on the front door starts again. This time I’m done, I’m not going to answer. I explain what’s happening to the roommates, and they don’t answer either. She spends the next hour screaming threats at the front door, crying and pounding on the door. I was just about to call the police before she left. The next morning, she repeated the whole thing with a bigger bouquet and slightly less screaming, more pitiful crying, but it lasted only about 15 minutes, cause I threatened to call the police through the door and she called me a ‘limp dick motherfucker’ and ran away. I saw her only once more, about five years after, and after a friendly hi, she told me that she was really glad we hadn’t dated. Because she had a new boyfriend now, and that I was probably never going to change my mind. The guy was there with her, and I’ll admit she was a hottie, but the guy looked like Quasimodo.”

(Source)

Whoops

“Things were going good, I mean real good. The city was celebrating its glorious playoff victory. The local heros were one win closer to winning the Stanley Cup. Women were, shall I say, juiced about the victory. Liquor was fueling the celebration and breaking down inhibitions. Enter me. Enter her. Me: ‘So, pretty fun night, eh.’ Her: ‘Yeah. Too bad the bar’s closing soon.’ Me: ‘Yeah.’ Her: ‘I have my friend’s place to myself tonight. Want to come over?’ Me: ‘Wait, what?’ 30 minutes later…kiss, kiss, hug, hug… Her: ‘Do you have a condom?’ Me: ‘No…’ Her: ‘There is a store up the road. Here are my keys. Bye now.’ Me: ‘OK.’ 30 minutes later…Ah…where did she live again?”

(Source)

His Idea Of “Dressed Up”

“A few years ago I met a guy at a bar who was born on exactly the same day as me. That seemed like reason enough to accept his offer when he asked me out. He told me to dress up very nicely as we would be attending an art gallery opening. I got all dolled up and when he came to pick me up, he was in a t-shirt and jeans. Okay, maybe I’d misunderstood the attire requirement. We got there and it was in a warehouse out in the middle of nowhere. It was actually an art gallery, but barely. Some of his friends were there, but he wouldn’t introduce me to them and proceeded to chat with them and ignore me the entire evening. Meanwhile, I’m dressed to the nines and they’re also all in jeans. After we left, he asked if he could take me out to dinner. I figured, whatever, at least I’d get a free meal out of this awful evening. We hit up a nice pizza joint and ordered a pizza. As I reached for a second slice, he just looks at me and says, ‘WOW! A second slice? Really? Jeez, you’re a house!’ So I ate the rest of the pizza.”

(Source)

Walked Out

“Not as mortifying as some I’ve read, but by far my worst date. It was a first date with a guy I met online. We’d had some nice conversations and decided to meet up one night for sushi. The night started off well enough, and I was really enjoying myself. About a half hour into the date, he starts getting a crap-ton of texts and calls from who he claims is his dad. Being the slightly naive girl (it was four years ago) I shrugged it off. But the texts kept coming. He never bothered to put his phone on silent and checked every single text. He said his dad wanted to go work out with him. At that point, I had a good handle on what was going on. ‘Look,’ I told him. ‘If you aren’t into me, that’s fine. But have the guts to tell me instead of relying on your buddy to bail you out.’ ‘Actually,’ he replied while standing, ‘it’s a booty call. Thanks for dinner.’ And he left. I sat there for a little bit, embarrassed as hell because of all the sympathetic glances from the other patrons. The server brought the check over, but she leaned down to me and whispered, ‘I heard what happened. I took that asshole’s order off so you only are paying for what you ate.’ That’s when I started crying in the middle of the restaurant. I left the server a massive tip for her generosity and spent the rest of the night drowning my sorrows in wine, Ben and Jerry’s, and ‘Love Actually.'”

([Source][https://www.reddit.com/r/AskReddit/comments/l8ack/whatisthebiggestfaildateyouhaveever_had/c2qmlfs/])

This Isn’t Going Anywhere…

“Not entirely a fail, but something out of the ordinary, especially in our age. I met this girl at college. She was one beautiful girl, and I even joined a choir to get to know her better. I felt good chemistry between us, and even our mutual friends noticed the reaction between us. Eventually, I built up the courage to ask this girl out on a date. Things seemed to be going fine until the end of the date. She told me she was planning on becoming a nun.”

([Source][https://www.reddit.com/r/AskReddit/comments/l8ack/whatisthebiggestfaildateyouhaveever_had/c2qlt9k/])

Gutterball

“Last year I decided to text a cute girl that I had class with the previous term to try to set up a date, and she responded with something like, ‘Sure! I was hoping I’d hear from you again!’ She said she’s a good bowler, so we agreed on bowling, and the day of the date rolled around the next week. She was sitting on the railing outside the bowling alley waiting, then when I got of the car and smiled at her she said, ‘Oh hey! I wasn’t expecting to see you here!’ I thought something might be up, but I couldn’t think of a good response, so I acted like I wasn’t expecting to see her either. I asked her if I should go inside and get a lane set up for us and she said, ‘Yeah sure, just hold on a bit…I asked another friend to meet me here.’ When I asked who it was, she told me that it was her friend that just so happened to have the same first name as me.

I went inside and handed over some passes for free games, put on my shoes, then put our 3 names in the machine. I didn’t want to just start without her, so after waiting for 10 minutes or so, I got a text from her saying, ‘Where are you? I really don’t want to be stuck here with this guy I used to have class with!’ So I found out that my instincts were right, but as a bowler with free bowling passes that were about to expire, I wasn’t about to just leave. I responded, ‘Sorry, family emergency, I can’t make it,’ and a minute later she came back inside and found me at whatever lane I was on. When I asked her about her friend, she told me that he wasn’t coming. When I asked her if she was ready to start, she then told me, ‘I’ll just watch, I don’t really like to bowl, I only really came to watch my other friend, supposedly he’s a really good bowler.’ After that I told her, ‘Well if you’re not going to bowl there’s not much of a point in staying, I was just going to practice for a match anyway.’ We said our goodbyes, and I never heard from her again.”

([Source][https://www.reddit.com/r/AskReddit/comments/l8ack/whatisthebiggestfaildateyouhaveever_had/c2qn298/])

Couldn’t Hold It In

“So it was date number two and she insisted that she wanted to drive this time. I had no problem with that and we decided to do the whole dinner and a movie thing. She picked me up at 5 and we headed to Cheeseburger In Paradise. We ate, had a couple of beers, and headed out. We had over an hour before the movie started so we decided to head out to a little city park that was about a mile from the theater. It was a nice day, birds singing, not too hot, gentle breeze. Little did I know how hard the coming crash would be. So, we’re walking this short loop through the park, making small talk, nothing too interesting, when I become acutely aware of that feeling. You know, the one that makes your lower gut feel like its about to mimic Vesuvius. That, or an angry badger has been camping in your gut and now wants out. Right fucking now. I didn’t say anything, just let her keep talking while I feverishly looked for a public restroom where I could decimate a stall. No dice.

At this point the urge had settled a bit. I figured the best course of action was to bee-line back to her car and go to the theater, where there was sure to be many public restrooms. So we headed back to her car. I should mention at this point that this date was particularly timid. Very sweet natured…but timid to a fault. Like she moved slowly and mousily (is that even a word?) and even drove 5 mph under the speed limit. Just as we pull out of the park, the urge comes back. This time it’s not fucking around. We make it about three quarters of a mile when we stop at a red light (that had just gone from yellow to red) and now we wait. And wait. And wait. After what seemed like an eternity the light changed to green. Mousy date then proceeds to move at 5 mph maximum speed to get to the movie theater parking lot. Then, as if Thor himself brought his hammer down on my colon, there was no holding back. As I white-knuckled her passenger door, the gates of my asshole let loose with a substance that can only be described as borderline inhuman. I can only describe the subsequent few minutes as a blur, because I hauled my shit-soaked ass to the theater’s bathroom as fast as I could. It didn’t really matter though. What was done was done, witnessed by any number of the bystanders waiting to buy tickets. I wasn’t sure who to feel worse for though…myself, or them for being exposed to it.

While I was in the restroom, I texted her ‘Just go home.’ Amazingly, she wanted to stay. I said, ‘No, seriously, go home.’ In the days and weeks that followed, the date actually claimed she didn’t care at all about the fact that I disgraced her car…she wanted to keep dating! Somehow, I wasn’t comfortable dating a girl who was cool with the fact that I took and enormous shit in her car. Later, I was diagnosed by a gastroenterologist with IBS. The event actually created some lasting social anxiety until one day I realized that was a waste of time and its a lot more fun to laugh about it. So I do. I mean, I’ve already shit in a date’s car…what’s the worst I could do?”

([Source][https://www.reddit.com/r/AskReddit/comments/l8ack/whatisthebiggestfaildateyouhaveever_had/c2qlhn9/])

Not A Great Ride

“The summer after graduating from high school I went on a date with a girl I had been friends with for a while. We decided to go to a fair a few towns over. We walk around, eat some fried foods, go on a ride or two. Things were going great and many laughs were had. We then went on a ride similar to a Zipper/Salt and Pepper Shaker. Lots of spinning upside down and so on. About halfway through the ride the funnel cake I had earlier decided that it did not want to remain in my stomach. With her sitting next to me I commence throwing up…and then we flip upside down…and my barf comes right back at my face. I had enough sense to keep most of it away from her, as she emerged from the ride puke free. I did not. We have now been dating for over 6 years, are currently engaged and will be married next summer.”

([Source][https://www.reddit.com/r/AskReddit/comments/l8ack/whatisthebiggestfaildateyouhaveever_had/c2qmdvx/])