Cringeworthy, terrible, awful, no good, very bad dates.
He Ran Over A Cyclist
“I moved away from my hometown and spent a couple years in a bigger city. When I moved back I was feeling pretty confident and I dialed up this girl I used to crush on, why not, right? It was not exactly what I would have done before I moved away because I was shy. Well, she seemed happy to have me calling her and we made a date to go see a movie.
We got to the theatre with about 5 minutes to spare only to find out the movie was actually playing at the theatre across town. It’s not that big a town, so it’s actually doable within 5 minutes so we go for it. We were both smiling – it seemed fun. Well on the way out of the parking lot I ran over a cyclist. I should probably just end the story there but basically, I just nailed her. I hit her so hard it literally broke the fiberglass on my jeep. The bike went flying off the sidewalk out into traffic and the girl came over my hood and landed beside my door to the point where I almost hit her with the door as I exited the vehicle. I was the worst company EVER during that date. It was just awkward.”
Confusing One Kristen For Another!
“There is this interesting (and cute) woman at work that I’ve flirted with from time to time. I recently gave her my number and told her to hit me up if she was ever free to go out for some fun. The key thing to note here is that her name is Kristen.
Fast forward and I got a text from a female friend (also named Kristen) who asked me if I wanted to check out a concert with her on Saturday night (also note, she posted on Facebook THE DAY BEFORE that she was getting a new phone number). We party a lot together so I had no qualms showing up to this concert after drinking a bit and in a t-shirt, jeans and a hoodie (not looking clean cut).
Out of the blue, I see my crush work-Kristen near the front of the concert. I went over and said hello for a bit then said I needed to grab a drink and meet a friend. I kept texting my friend-Kristen and she was replying that she was near the front. So once again I head down there. I chat for a bit with work-Kristen and keep looking for my friend.
I mentioned to work-Kristen that I kept texting my friend who I couldn’t find when at that moment work-Kristen says, ‘Is that why you keep asking me where I’m at?’
That’s when it dawned on me that it was NOT my friend who invited me out, it was my crush! I showed up a little wasted, disorderly and probably seem pre-occupied the whole evening. She seemed ticked off after that and has sort of avoided me since this past weekend. Oh well, c’est la vie.”
His Heroic Save Was Anything But
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“Went out with a girl in high school and did the usual, movie and a dinner. It had been going great up until dinner when she stumbled over a curb. I went to catch her and promptly whacked her in the face with my head. This actually broke her nose, which leads to me panicking and trying to fix it. Of course, that was a bad idea, and I think I made her nose bleed more, to be honest. Thankfully she wasn’t upset at me (I spent a good half hour freaking out over it), but there was a veeeeeeeeeery awkward and at one point terrifying conversation with her dad when I brought her home. He was a former Marine who served in Vietnam and did the usual ‘scare the bejesus out of the daughter’s date’ by coming out sharpening his Kabar knife when I picked her up. Needless to say, he really didn’t like or trust me after that.
The girl and I dated for a year and we’re actually still pretty good friends, so I guess it worked out okay in the end.”
A Dead Beat Can’t Pay For A Date
“I had been talking to this girl for a few weeks. Nothing serious, but the obvious flirting and talks of ‘We should get together soon!’ The biggest problem is just scheduling and she lives about 40 minutes away. Lo and behold, one night she texts me to tell me she has business in a city 10 minutes away and will be staying in a hotel that night. It’s obvious she’s telling me this because she wants to hang out, so even though I had plans on staying in and ordering a pizza (which I had already done), I decide I can’t pass it up. So, I get dressed (and in the meantime, I pay for the pizza that’s delivered and throw it in the fridge) and head her way. On my way over there I stop to get mints and rubbers (the eternal optimist that I am) and when I go to pay I realize that my bank card is laying on my bar, right on top of my Papa Johns receipt.
D’oh.
It’s too late to turn back, so I count out my cash ($34) and pray to the old gods and new that I can swing a first date with just $34. I’m hoping that she’s already eaten (it’s already kinda late, like 8:30). I get to her hotel and head up to see her. Sure enough, she’s already looking for restaurants. I play it cool and say we should stick close by because she was in the airport district which means it’s mostly sports bars for travelers. She mentions two nearby restaurants, and I had never heard of either. One is some kind of grill, so I assume that would be some greasy diner where you could get food for $8 a piece so I say that sounds good.
We pull up to the place, and lo and behold, my greasy-spoon diner is actually one of the fanciest places in the city, and all parking is valet. That drops me down to $29.
We walk in, and not only am I severely under-dressed, I’m also extremely aware that I can’t afford a simple appetizer at this place. We sit down, and I immediately check the menu to see the damage. This is the kind of place where a single meal goes up into the triple digits. Even if I HAD brought my card, this place is out of my budget.
At this point, I realize all I can do is just sit back and enjoy the trainwreck that’s going to happen. I mean, I could have just told the truth, but that’s no fun. So, she first orders a drink, bringing me down to $20. I decide, either way, she’s going to be paying for this, whether she knows it or not, so I order glass for myself. $11 left. We make small talk while looking at the menu, and I start going on about how all of the food looks so gross. This is my way of saying I won’t be ordering that much. Finally, after her continuing to convince me to try this kind of steak or this kind of seafood, I explain I’m vegan. I’m not vegan. I have a sausage pizza waiting for me at home. But, that’s how this date is going; I’m now a vegan.
Well, she decides to order lobster crab cakes as an appetizer. I’m now in the red. I don’t touch the crab cakes because I don’t want to be on the hook for them when it comes to announcing that we’re going dutch. Finally, it’s time to order the main course. She orders some steak and rice concoction, with a side of sauteed spinach. I muster up all the confidence I can and order a Ceaser salad off the appetizer list. That’s what I play with while she’s chowing down on this delicious looking steak.
We had gotten there kinda late, so the servers are subtly rushing us out, but nope…she wants coffee and dessert. So while we’re waiting for the flourless cake she HAD to try, I’m really trying to figure out how I’m going to break it to her that I only have $29 to contribute to this fine dining experience. Finally, the waitress brings over the bill, and for a moment I honestly consider pulling the ‘going to the restroom’ routine, but something strange happens. My instinct kicks in when I see her grab the check and I actually say (out loud) ‘No, that’s okay, I’ll get it.’
I’ve never felt so suicidal. Not because I was depressed, but because I knew immediately that nobody this dumb deserves to live. Thankfully she says, ‘We can split it.’ So, I wait for her to put her card in, and then quickly shove my cash into the little folder thing, and put it up for the waitress to take it away. It’s one of those weird things where I know I’m going to get caught, but I’m savoring every second of stalling I can. The waitress comes by, picks up the bill and scampers off. I’m so relieved that neither of them made a big deal about me contributing $29 to a bill that’s easily over $100. Just as I’m about to give a huge sigh of relief and actually pay attention to what my date is saying, I see the waitress walking right back to us holding the bill.
‘Did you want me to just take the $29 and use the card for all that’s left?’ Why would she ask me that?! What else would she think my plan was?! I’m convinced she did that just to really drive home the fact that I can’t afford this place or this date. I just respond: ‘yes please, that’s fine please, thank you,’ to get her out of there, but the damage was done. My date just stared at me, then her phone.
The bill came back, my date got a VERY good look at the amount I contributed, then, as if to really kick me while I’m down, she pulls out her phone to do some stupid tip calculator. We finally left, and after meeting her and talking with her, we didn’t really click; totally different interests and not much at all in common, so that was the end of that. At least I still got that pizza later that night.”
That’s One Way To Meet The Parents
“To preface this, I’ll say that I’m a big guy, 6’5″ about 210lbs and very clumsy. The first time I met my ex’s parents was at their house and I fell down the stairs. This alone is bad enough, but sitting at the bottom of the stairs was her parent’s beloved chihuahuas. I killed one of them and paralyzed the other, I also fractured my patella on the way down.”
Everything Goes Wrong
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“We went for Thai food. We both got the same spicy eggplant dish. Each dish had one tiny pepper from which it got all its heat, and we dared each other to eat them. He spat his out right away. In an effort to impress him, I swallowed mine. It wasn’t bad, at first. And then my mouth was a cataclysm. The waiters brought several glasses of milk so I could be cogent again.
Initially, everything seemed okay after that, but then I had to go to the washroom, which wasn’t terrible. But then I had to go to the washroom again, and again, and again. Half of our dinner date was him sitting alone while I exorcised this pepper from my bowels. Remarkably, he didn’t seem too irked about it.
We were downtown and, both being kids from the suburbs, decided to go window shopping at the local stores. We got separated briefly while inside a clothing store, which I was alright with because there wasn’t much chemistry between us.
Suddenly, I had to poop. I had to poop immediately. I ran to the nearest store attendant, begging him to let me use their washroom. No success. I dashed to the next store, and still found no toilet. Nothing. It was a desert and my butthole was about to rupture. Then finally a store let me in! Success! I darted down their stairs to the sweet relief of porcelain but, just as I reached it, my bowels, as if it in a fit of cruelty, let loose.
I sat there contemplating what to do. ‘Do I message this guy? What do I say? How do I deal with the fact that my pants are filled with poop? Why did this happen? Which god did I offend?’ I opened my phone. No reception. ‘Okay, well, at least that’s dealt with.’ I cleaned myself up, slowly and meticulously. I used all of the toilet paper available in the washroom and then improvised. I went commando. An hour passed and I left.
He had disappeared, shockingly. I took public transit home and spent an hour on the subways and buses convinced that everyone knew. I felt marked. My friend texted me and asked why I had ditched him, and then I remembered that I was supposed to have met him directly after the date.
I told everyone I had gotten violently ill. I guess, in a way, I had.”
Passing Out Doesn’t Leave A Good First Impression
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“I snuck a bottle into a movie. At some point, I passed out. I awoke to a clinking noise. I realized the clinking noise was my empty bottle, which had slipped out of my hands and was rolling down the sloped floor under the seats, toward the screen. I saw backlit heads turned toward me with curious and annoyed faces. The seat next to me was empty. My date was gone.”
His Nerves Got The Best Of Him
“I was always a nervous kid.
So, with my first serious girlfriend, we had just discovered getting physically intimate together and happily engaged in the activity quite often. She also enjoyed a bit of schadenfreude in a relationship. Not a lot, just a streak of it that reared its ugly head from time to time. Also, she may have been a little crazy.
So we were 17 years old, and one evening at a local diner. She tells me that she thought she was pregnant.
Well, that little nugget of pregnancy-related information just ate at 17-year-old me throughout the course of dinner. Just marinated in my mind, and folded over and over. Dinner ended with me barfing into the diner’s Ficus pot that luckily happened to be next to the table.
Deep apologies to whatever waiter/waitress that had to clean up the puke Ficus that night. We then got a store bought test and thankfully, it was negative.”
A Woman Passes Out In The Tub
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“I had a massive crush on a guy for months and he finally asks me out. I was so nervous that I drank half a bottle of port on an empty stomach before going to meet him.
We head out and he takes me to a new bar his friend has just opened and there are drinks on the house. Everything was becoming a blur and I was feeling no pain. We decide to head back to his place via cab. This is when I recreated the scene from The Exorcist in the back of the vehicle.
After him tipping the cabbie an extra 50 to fumigate his upholstery, we head into his cool flat where we both agree I need a bath. Cue hot soapy bubbles from this long-suffering guy and I manage to lock the door and sink under the sweet-scented foam. Bliss. Until I come round with him dragging me out of the bath – apparently he’d been knocking for a while and I was semi-conscious and slipping under the water.
Wake up in his bed naked the next morning, horrific hangover with the bathroom door kicked down and the doorframe in splinters. When I asked if we ‘did it’ he replied in the negative, stating ‘It would have been like necrophilia.’
Amazingly we did continue to go out for quite a while after that,”
A Boxer With A Medical Condition Makes For An Uncomfortable Date
“I used to box quite a bit in high school and after a solid month of convincing, I finally got this girl to go on a date with me. She was gorgeous, a blonde cheerleader, super nice girl, and that’s what took forever to get her to date me. I don’t think she really trusted me or felt comfortable around me as my friends and I were really rowdy and dumb. Anyway, the date was set for Saturday night but I had a fight on that Friday. I had just recently moved up a weight class and got pretty beat up. So anyway, we were just going to go to dinner and a movie, typical high school stuff. I pick her up and go to dinner. Dinner goes well, she;s actually opening up to me which is nice as I could tell she was super shy. As we are leaving, I opened the door for and turned away from her to sneeze and sure enough, blood goes everywhere, I mean it’s a volcano of blood. She runs back inside and grabs napkins but we can’t get my nose to stop bleeding, so she drives to the hospital right down the road and we sit in the ER for like an hour. It turns out I have a pretty bad cut on the inside of my nose and sneezing ripped it open. They put this jelly stuff in there and basically tapped a little cotton ball type thing in there. So we are leaving, totally missing the movie at this point, and as we’re walking out, I sneezed again…
Again, blood everywhere.
At this point, I’m apologizing like crazy but she’s kind of frustrated I guess. She calls her parents to pick her up. We didn’t really talk much after that. Sucks too, she sure was pretty!”
A Man Admits To His Date That He Likes Her Friend
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“Freshman year college it wasn’t I was flirting with this girl name Lindsey at a party and she was not into me at all. I kept trying to talk to her and she would flat out ignore me. So I ended up talking to her friend Sarah and bringing her home. I used to live in the dorms and shared a room so we ended up laying in my tub so we could hook up. Sarah stops kissing me and asks, ‘What do you think of Lindsey?’ And with no hesitation, I say she’s gorgeous. She then asked what I thought of her and I paused like an idiot. Then replied, ‘Oh you’re pretty too.’ Sarah begins crying like crazy cause everybody was apparently into to Lindsey. Then my roommate starts banging on the bathroom door cause she’s crying so loud and basically just kicks her out cause he had work the next morning.”
A Man Loses His Dignity, Among Other Things
“So it was a very nice summer evening in early August. My girlfriend (we’ll call her Sam) at the time and I were going out for dinner at a local steakhouse. Halfway through our reasonably priced meal, Sam went to relieve herself. I, however, did not. Fast forward 30 minutes. I had paid for the meal and were on our way to Sam’s house. It was at this point I realized I should have gone to the restroom at the restaurant. But I think to myself that I am the master of my own domain and I shall not falter. Another few minutes of walking, I see a public restroom, but as previously stated I am the master of my own domain. We are now only a block from her house. Pressure is building and a few enemy troops break the line. I remember distinctly thinking ‘I got this.’
We were now at her house and the pressure is at an all-time high. As she reaches for the gate the floodgates release. I may not be the master of my own domain but I have a plan. We enter her house and so far she hasn’t shown a single sign of noticing. There was no smell at all less than an average fart at most. I made a b-line straight for the washroom to inspect the damage. Everything was fine till I had to remove the underwear. Some ended up on the floor and I don’t know how long I was in that bathroom for but it seemed like ages. I had to do something so I peeked my head out the door, looked Sam dead in the eyes and said ‘hey hun I just threw up. I think I’m going to head home.’ She proceeded to ask if I was alright I said I was just going to head home. I packed my underwear and dignity into the bag I had with me and left. When I got home I took a shower with my clothes still on and contemplated life.”
Social Anxiety Takes Over And A Young Woman Freaks Out
“In 2009. the beginning of my freshman year of college, I was super awkward and dealing with some social anxiety, but as part of a deal with my parents, I put on my big girl pants and forced myself to attend some social events that my dorm put on.
It was okay. I didn’t get along with the girls on my floor, for unrelated reasons, and it seemed like everyone had already made friends. So I ended up chilling in a group that might as well have had a sign that said: ‘socially awkward misfits, please congregate here.’
I ended up talking to a few other awkward folks like myself and fortunately found that we had some things in common in terms of tv shows and books and things. I had recently started watching Doctor Who and when one guy mentioned it, my brain went into ‘Yes! Something I can talk about!’ We ended up chatting about it for a while and he asked me to meet up with him that weekend to watch some episodes.
We ended up hanging out a few times, going on a couple of lunch dates, meeting up in the dorm common areas to watch Doctor Who, holding hands, kissing a little bit, but never anything more than that.
I get home from classes one day and, bear in mind, I haven’t heard from him in a day or so, to find that I have a relationship request from him on Facebook. I don’t know what my brain did at that point, but I totally panicked.
I turned down the request, deleted him from Facebook and spent the remainder of that year in the dorm literally hiding if I saw or heard him coming down the hallway. I got a few messages asking me what had happened and I never answered them. I apparently went into complete and total social-anxiety driven insanity.”
A Guy Is Talked Into A Ride He Doesn’t Want To Get On
“In my senior year of high school I had been dating this girl for a couple of months and things were going pretty well. Then the county fair came to town, which to our small town was a big deal, so of course, I took her there to do all the classic fair activities: funhouses, games, crappy food, rides, the whole shebang. However, I made the terrible mistake of eating before I went on a ride dubbed ‘The Zipper’ (the ride basically rattles you around while spinning you). I do not do well with spinny rides but it was a new relationship and didn’t want to say ‘No’ quite yet, so I went on against my better judgment. I got in the ride and every thing was fine for the first couple of minutes. After that I told her I wasn’t feeling well and to stop the ride. Then disaster struck. I puked up nearly an entire serving of fries and half their weight in ketchup. After that, I was pretty much covered in my own vomit walking around a small town county fair with my new girlfriend so pretty much everyone knew within the next day or two. I was eventually able to get a friend to drop off some clothes so I wouldn’t have to walk around too long like that.”