20 Guys + Gals Reveal Their Worst Date Stories — Ft. Brooke Freed

I think we’ve all had our fair share of “good” dates, “bad” dates, and “somewhere-in-the-middle” dates. However, we can all agree that even through the ups and downs, dating is fun! You get to eat food, drink drinks, all while learning about someone who could potentially be “the one” (for the night or for the rest of your life.. no judgement). The point is, dating is essential to finding a partner.  Of course, everyone has their own interpretation of “the perfect date”, and sometimes dates are far from perfect. Here you’ll find that you’re not the only one that’s experienced some terrible sh*t.


To kick off the storytelling, here’s one of my own…I snuck another one in here somewhere 😉


I was serving cocktails on the patio of a really nice restaurant in St. Louis. The restaurant was hosting a Match.com party and it was my first time serving a party so I was really nervous. You should also know that the patio was cobblestone and I had to wear a little black dress and heels. The first people to arrive were two men. Both of them were in suits with bowties and resembled Pee Wee Herman to be completely honest with you….Have a good mental image? So I walk up to the guys and take their orders (they got Bud Lights in case you were wondering). As I’m bringing the drinks to them my heel gets caught in the cobblestone. Unfortunately for them I was within arms reach of their table, soooo close to setting the beers down. Instead, the beers along with the tray flew out of my hands directly onto their laps. They did end up staying for the whole event for whatever reason but they went home alone. And that, my friends, is how you successfully ruin a date.


  • The date actually went great until I broke my arm during the date! Ended up in the hospital, the guy went with me because he felt bad if I went alone. Ultimately we saw each other for about a month but nothing else bad happened during that month!” – Grace, 25


  • “So I was supposed to take acid with my friends but I forgot that I was also supposed to go out to dinner with my gf and her parents that night too. So I took the tab right before they picked me up thinking that dinner would take an hour or so and then the acid would be kicking in right when they dropped me back off after dinner. Well… dinner took three hours, I could tell I was acting weird in front of her parents. At one point I had to have my gf cut my steak into pieces for me because I couldn’t do it and I also went to the bathroom for 15 minutes to call my brother so he could calm me down. Longest dinner date of my life.” – *Sean, 24


  • “Met this guy at University of Arizona during my short time there. He was president of his frat, jewish like me, and was brilliant. I figured I really found a good one. Our first date was smooth. Ate a decent meal and he picked up the tab. The second date was god awful. We went to this place called Mama’s Hawaiian BBQ. The place actually was recently shut down because It was a front for a major drug dealing operation, how pleasant! Anyway, it’s the kind of place where you’d go after a long night out. Not exactly how I  pictured a date with a man that’s trying to impress me. He orders first and pays for himself and looks at me to order. I order, turn to my side where he was standing and he’s already grabbing a table…. So reluctantly I had to pay for myself. We sit down and he starts eating. This time he has apparently lost all of his manners. Mouth open, chewing loudly, slurping his drink and making a complete mess. I finally asked him if he  just wanted me to go because it didn’t seem like he really wanted me there… (that would make two of us). But he responded by saying he was having a blast with me and didn’t want the date to end. In fact, he wanted me to spend the night! (LOL)  I grabbed a to-go box and sat there without saying a word, making probably everyone around us uncomfortable (goal achieved). When he finally finished eating and talking about himself I ended up refusing a ride home from him and instead walked back to my Dorm.. NEVER AGAIN!” – Brooke, 24

Another personal story of mine. Clearly I not only ruin dates for other people but I am pretty good at picking men who can ruin my own.


  • “Once I was on a date at Applebee’s. Afterwards we went on a long bike ride. She ended up shitting her pants on the ride home and I did as soon as we were in the driveway.” – *Britney, 21


  • I invited a coworker that I didn’t know all that well to go to homecoming with me in high school. She was a vegetarian, which she failed to disclose, and I took her to a restaurant where there weren’t that many options. Then I realized I had forgotten our tickets when I got there. And then she was bored at the dance and spent the whole night hanging out with a girl she ran into there who she knew while I went and partied with my friends. It was, all in all, a super lame date.” Andrew, 41


  • “When I was 18 my parents and I were at the back of a store and this guy who was kind of cute and 23 asked me out to a Cintas dinner. My parents let me go and said it was fine so I agree to go on another date with him. He was significantly different. He was an undercover emo guy who bragged about smoking K2. He then brought me to his apartment where we rented the hulk. He smoked a bowl of his fake pot. Then decided this was the moment to kiss me. It was disgusting. I think he had a dead tooth. So almost immediately I told him that he had to take me home. He asked me what I thought of the kiss and I told him it was whack. He cried. Then texted me the next day and told me he bought me a bunny. I blocked his number and never spoke to him again.” – Michelle, 25


  • Once I picked up this person I really liked for pizza and beer at my place, and they went to use the restroom, there was a loud crash, and they were gone for a really long time, like, an amount of time where you start getting worried you should see if they’re okay, but what if they’re actually just using the restroom and you embarrass them? So, after, like, forty minutes they come out and ask to be taken home, they have a bloody nose, they hit it on the bathroom sink when they had a seizure. They said it happens when they get really stressed out and they never went out with me again.” – Syd, 26


  • “I went on a date with a guy I met on jswipe [a Jewish dating app].  We met at an upscale bar in Santa Monica overlooking the ocean. We order drinks and sit down. By the time I’d finished my first he’d already downed two. He asks for the check and proceeds to ask me to pay for my share. We both pay and he ends up putting just a dollar for tip and as we both get up, he reaches for my glass; chugs down the melted ice, takes the orange that garnished my drink, eats it, and finally says to me,  “so I’m guessing we won’t be seeing each other again”. – Ariel, 25


  • “We went to a party like freshman year or something and the cops busted it and made all the driver’s do breathalyzer tests before any of us could go and so I was waiting and drunk and had to go pee really bad so I ended up peeing my pants and then got into a guys car and pretended like nothing happened and he called me out for it after they dropped me off” – Lindsay, 23


  • “Date story: first, didn’t realize it was a date. Second, we went to the zoo and then went to Denny’s. in the Denny’s parking lot, he literally grabbed both side of my face and smushed his face against mine. Did not kiss back. He was ecstatic and kept trying to hold my hand in the car. Had to avoid him at Webster ever since. Another date story: Tai [current boyfriend]  told me directions early in the morning after we had gotten off work and eaten at Courtesy Diner. He surprised me by giving me directions to the graffiti wall by the river, and told me he wanted to watch the sunrise with me there. We started driving back to actually take him home, and he turns to me and goes “do you think I can fit your whole fist in my mouth?” I said “well.. my fist is really small, so maybe-” “Let me see” he curls my fingers in a ball, shoves my hand in his mouth, and just looks at me. I said “I guess you can.” He takes my hand out of his mouth, looks at me again and pauses, and then said seductively “did you like that?” I was like “it was impressive?”And then he tried to get me to put his fist in my mouth. And the rest is history.” – Kira, 24


  • “When I first went to college my dorm roommate and I went to an open mic. There were these two guys that did a duo act. One of them was so attractive and honestly completely my type. When we went back to the dorm I mentioned how cute the guy was. My roommate said she knew him and took it upon herself to set us up on a date. Honestly I was pretty excited… until my date showed up and it was the other guy in the duo!! As shallow as it sounds he was the exact opposite of what I am interested in. However i was going to be polite and go on the date. He ended up being totally clingy, would randomly show up in the art department studios, & I of course had to tell him I was interested. But considering he was best friends with the other guy, I was never able to go out with the one I actually wanted to go out with!” – Paige, 23


  • “A few years back, this girl I barely knew from some Jewish young adult group I was in, asked if she could set me up on a blind date. I said I wasn’t comfortable with that, which she translated to “send a perfect stranger my email address to arrange a date”. He was a med student and Jewish, so I guess she just assumed he was every Jewish girl’s dream. I decided it wasn’t that poor guy’s fault that girl was an idiot and decided to give him a chance. We went to dinner and he determined that the the amount of water I was drinking to fill the awkward gaps in the conversation were the sign of a medical problem, and he spent the meal trying to diagnose me. And he alternated that with talking about what we’d do when we’re married. Married? Like he ever saw me again. Also went to dinner with a guy who described how after some tsunami in Asia, workers had to comb through the bodies for foreign nationals to return them to their families. And then he asked why I didn’t finish my meal. My friends convinced me that he was probably just nervous and to give him another chance, and he spent the next date talking about his cat’s sex life. No… really.” – Louise, 32


  • “So this was when I was living in STL and I was on tinder. I was talking to this guy (can’t remember his name so I’ll call him Matt). In his pictures he seemed tall and handsome. Very fit and he told me he worked out several times a week. So me and Matt had been talking on tinder just long enough for me to not find him sketchy so I gave him my number and we texted. He said he had an annoying roommate and asked to meet at my place. I agreed and when i went out to meet him he had this mustard yellow beater that had a bad loud muffler. And the person that got out of the car was NOT the guy in the pictures. Or rather, they were probably him from like 7 years ago. He was not fit like the pictures. He was fat. And so we just hung out and smoked in my room and then I lied and told him I was super tired and he needed to leave and kicked him out and ate a bowl of cereal by myself. Weirdest experience of my life. I’ve never been catfished before.” – Samantha, 22


  • Sophomore year of college met a girl at a bar, hung out twice with her. We ended up hooking up. Anyway 3 days later she wants to hangout again. I meet her at her house, ended up meeting her entire family…when I say her entire family I mean that literally (grandparents, aunt’s, uncle’s, etc) she told her family that I was her boyfriend of a year and that I was invited to her cousin’s wedding. So I had to sit through an entire family dinner pretending to be her bf. I was a gentleman and didn’t call her out in front of everyone. But after that incredibly awkward dinner…never called her again nor spoke to her after.” – Geoff, 25


  • “So this would have been last January I was coming to Denver for a cannabis career fair and the guy I’d been dating had just moved out here and I was only gonna come for the day and fly back after but after basically begging me to stay longer to “get some Dick” (his words not mine), I was like ok fine but I wasn’t gonna get a hotel room just for that so he ends up hinting at me coming to visit and Donette (ex bfs mom) was like oh well have him stay here with us! I was like ok that’s nice. The whole day he was like how are we gonna get her to leave us alone long enough to go fuck I’m like wow you’re hard up. Snuck down to the basement and did it on an old desk looking up at a portrait of his ex the whole time. I was like wow. New low” – Bobby, 26


  • “We were both going at it, like normal white boy missionary gay vanilla sex and he was fucking me. For some reason we had to pause for a second so he could reinsert himself. When he did, my ass made, like, a queefing noise because I was loose (he was a big boy.) and I kind of laughed about it. Which made me queef even more. This annoyed him and i just kept queefing and farting and couldn’t stop and we eventually had to forfeit and start again later. I enjoyed this moment, but he just wanted to get off.” – *Ben, 25


  • “Once I was meeting someone from Tinder. They deleted their Tinder and I honestly didn’t remember what they looked like other than the basics. When I got to Tani I looked around to see if anyone stood out waiting for a date or waved me over. I saw a guy who I thought was my date pondering the menu seeming somewhat lost too so I assumed it was him. I went over and gave him a hug and sat down. He barely spoke. A few minutes later his girlfriend returned from the bathroom, lost it and asked who the hell I was. …it was really romantic.” – *Alana, 26


  • “One time I went on an okcupid date with this girl who ordered some lobster ravioli and I don’t know if she was concerned with taking bites that were two big or talking with food in her mouth but she cut every regular sized ravioli into 6 pieces and ate them one at a time. I finished my egg n cheese sandwich in about 10-15 mins and she took 45 minutes to eat all her ravioli. Haven’t spoken since” – Andrew, 25

Written by Brooke Freed

  • Image taken from theCHIVE.com (google images)


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