Cringe Worthy Dating Stories By Locals

Cringe Worthy Dating Stories By Locals

Doom doom doom doom, do you want them in your room?

By Georgie Murray | 12th February 2020

We’ve all got one that will forever haunt our souls yet make us laugh. Yes, dating disaster stories provide endless entertainment and torture, but boy-oh-boy they can be hard to endure. Happens to the best of us, right?

With all the romantic flurry of love thanks to Valentine’s Day, I thought we should keep it real and shine a light on the bad, the worst and the most embarrassing on the adventures of dating. Enjoy, and happy V-Day. 

Fire Trucks And Sushi

Second ever date after a four-year relationship and this guy took me to a cool Japanese restaurant. We were a little early so they made us wait in their small bar area. I was already nervous because I don’t really go on dates, so we got a drink and waited about 10 minutes before our table was ready. As I went to stand up, I almost completely fell over as my foot was dead! Not the ‘I have pins and needles’ type, I literally could not feel my foot! Every time I put my foot down and every time I tried to put pressure on it, I would roll my ankle (the people behind me probably thought I was drunk). I then had a message from my best friend (who I live with) telling me that I had left my hair straightener on and set our apartment on fire and there were firetrucks outside our apartment. I was freaking out at this stage while attempting to try and walk to the table. I called her to see what was going on and she said, “Sorry, darl, that was a joke. I knew you were on a date, but your mum called and I forgot to message you to tell you that.” This poor guy then says, “Wow this has been a rough 10 minutes for you,” and orders food for me as I hadn’t been there before, which was a big mistake. I only enjoyed one thing he ordered and had to pretend I loved it all. He seemed so impressed with himself. Poor guy.

Bathroom SOS

I had been kind of seeing this guy overseas. We met here in Australia and he soon moved back to the UK but we kept in contact. I happened to be back in the UK for the second time in a year for family stuff so naturally, we caught up. It was my first night there and we went out to dinner with his two best friends, who I was meeting for the first time (so yes, there were nerves). I politely excused myself to go the bathroom, desperate for a wee! To get descriptive, the toilet roll holder thing was enclosed metal, and the roll had rolled all the way up, so I had my hand right up in there, grasping for paper. And then. my hand got stuck. I wear a ring that I’ve had since I was 18 with a lot of sentimental value and it was the one thing stopping my hand from wriggling out of the metal cage. After a while of almost breaking my hand, I had managed to wriggle my finger out of the ring and set my hand free. I returned to the table a bit flustered and tried to quietly explain to my date/friend what had happened and that I need to get my ring back – there was no chance I was leaving it behind. He couldn’t do anything and just laughed so I had no other option than to try and explain the situation to the cashier who could barely speak English, let alone understand an Australian accent. After a brief game of charades, the cashier was able to unlock the cage and my ring was rescued. Safe to say, I’ve never wrangled for toilet paper like that again.

GST Included?

So, there’s nothing like getting an invoice after a night out… I had been seeing a guy for a few weeks and we were out one night for some drinks. I’m the type of girl who doesn’t expect a man to pay, but a few drinks here and there is a nice gesture. He bought me two drinks and paid for the Uber home (so I mean, not bank-breaking stuff) and made a comment about how much he had spent on me. Jokingly, I said “Oh sorry, why don’t you just invoice me then.” I kid you not, the next morning I received a text message with his bank details and a request for $50. Seriously?!

Sleeve Sayonara

I had a small thing with this guy on and off. Firstly, our impromptu ‘date’ was when I had ducked out to grab something and was in my pyjamas, hair up, no makeup or bra. Long story short, a few wines were had and a sleepover ensued. The next morning when he was dropping me off at my car, I had just thrown on anything as I was going straight home to get changed for work. The awkward goodbyes were exchanged and I gathered my things and was on my way. As I was juggling my phone, keys, shoes etc. my arms were full and I closed the door, not realising that my sleeve was caught in the door. For context, it was a Tesla so they don’t have standard door handles. As I tried to pull my sleeve free, he thought I was just hanging around for a lingering goodbye and nodded his head, smiled and waited for me to step away from the car so he could actually leave. Turns out Tesla windows are thick too, so I couldn’t hear what he was saying. I had to pull my arm out of the sleeve and up through the neck hole of my shirt with a little wave to show I was stuck. He had to lean over and open the door to set my arm free. I made a quick exit and that was that. We didn't see each other for a while after...smooth.

Vomatron Verified

I had just flown 24-hours on a family holiday but was staying with a date for my first night there. I had flown in that morning but not napped and got stuck into sight-seeing straight away. I hadn’t seen my date for over a year so he’d arranged dinner and a night at a hotel. I was nervous. We checked-in and made our way to a bar where we sampled the cocktail menu. It was then that I made my first mistake. I was feeling okay but was worried I was in for a big crash so took a No Doze in anticipation of the jetlag wave. After mixing spirits, we made our way to a very hearty meal with a bottle of red wine. I was feeling great! Tipsy but tuned-in, we kicked-on to a bar/club and did some tequila shots. Not long after I wasn’t feeling too great and it was time to go. I walked ahead out of the bar thinking he was right behind me. Turns out, he wasn’t and I found myself a nice curb to sit on in the drizzling rain and apparently thought it was a good spot to have a few sneaky voms. I sat there vomiting up my guts and then pulled myself together to go and find him. After a few missed calls back and forth we found each other and he was not impressed! We weren’t in the most fancy or salubrious part of town and he was asking around if anyone had seen me. A group of guys pretended they had and said they’d only tell him if he pays up. He handed over about $60 Aus dollars (40 Pounds) and they walked off. Nice to know I was worth the money though, right?

For the record, the night of embarrassment didn’t end there. Upon returning to the hotel, my unsettled stomach returned, too. Lots of vomit on the hotel room floor later and I was out like a light. 

Pasta Disaster

It was my first proper date with a guy I’d been seeing and he offered to cook at his place, which was a first for me. I was impressed! After struggling to find his place, I nervously arrived but was soon eased into the situation with a glass of wine. Dinner was served – pasta with lots of red sauce. As I was eating, I dropped a huge spoonful of pasta all down my front, leaving a sauce trail all down my black and white striped dress. Two minutes later, as I was having a sip of my wine, the dog jumped up on me and knocked my arm. Of course, I spilt all the wine over me and the floor, too. From memory, I think the glass may have also smashed! I sat there, a pasta disaster and wine swine, but I did get a second date!

Spanky Panky

You know the whole ‘accidentally’ leave something at the house of the guy you like trick? Irritating as hell, but nonetheless a very effective tactic to see the man again… or not. So, my girlfriend and I were on a double date - well, I guess it was more of a group “hang out” at one of the guys' houses. It was all very innocent – we were sat on the couch watching movies together and he had his arm around my waist. I suddenly became conscious to the fact I was wearing Spanx and he might be able to feel them. Now, I’m a little self-conscious (yet an avid lover of Spanx) so I’m not talking the ‘cute pull my tummy in a little Spanx’, I’m talking the ‘full firm control bodysuit and make me look 10kg lighter Spanx.’ I decided I’d go to the bathroom and remove said Spanx. But, given that they covered my entire body they were too big to squish back into my tiny little handbag. Naturally, I tucked them under my arm, returned to the couch and hid them under the couch cushion (totally logical right… don’t even ask). After the movie finished, we all chatted a little and then my girlfriend and I headed home together. Well, I wish. Turns out not all of us because… I LEAVE THE DAMN SPANX BEHIND. I wonder how long it took him to find them. What did he do when he found them? What went through his mind? Did he definitely know they were mine? Let’s re-close the lid on this one and never speak of it again. 

Three's A Charm

When I was single I used about three dating apps. I went on about 50 dates over a three-month period and kept the coffee industry alive. I was about to give up and on my last day of dating, I ended up going on three separate dates (that magic number, apparently). Morning coffee was a quick ‘no' and when I met my lunch time date, the first thing she said to me was, "You have two choices. You can stay or go… it’s not a problem." The Brazilian lady looked nothing like her photo and I guess I was interested because she was Brazilian… shallow I know. I wanted to run but thought, no I’ll stay and running away seemed a mean thing to do. We sat and chatted for an hour and a half and she told me she had fled Brazil to escape a violent husband and that she was living in someone’s garage. We had a great conversation but it was definitely a no from me. The third date was going to be my last, no doubt about it, I had had enough. We met at 7pm on a Saturday night and I dropped her home at 10pm Sunday night and we're still together after seven years!


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Article by Georgie Murray

Georgie is a Journalist with a knack for bad jokes and dating disasters. A total open book, there’s no topic off limits for this Rod Stewart enthusiast. Starting her career in Broadcast Journalism, Georgie has since gone back to basics of the written word with a particular love for taboo topics and fashion media.


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