13 Of The Worst Date Stories We’ve Ever Heard

Because we've all been there!


by Grazia |
Published on

The dating world is a tricky business. And with the rise of dating apps like Tinder, Bumble, Raya (insert cool new dating hub here) it just got a whole lot more complicated.

But for every great date, you might have to endure five awful ones. Which can add up to some really, really awkward stories. You might meet someone who collects scary china dolls for fun, for example, or a guy admits to once having put a pig's head in their housemate's bed in the name of revenge (No? Just us?)

But while bad dates can be a scary prospect, the best way to get over them is to share them, spesh in the lead up to Valentine’s Day next month. So, in the name of sorority - and hearing some great tales of what never was – here’s the 12 worst dating stories we’ve ever heard (which may or may not include stories as told by Grazia staff)…

The One Where I Was Hit By A Car

Having spent a good hour trying to recreate Taylor Swift’s Fearless-era hair, I was running late to meet someone for a second date. I dashed out of my student house, and started to cross a side road. Distracted by my phone, I wasn’t entirely paying attention when an Iceland delivery truck turned off without signalling, hitting me just above the knee and sending me flying. When a car hits you, your life really does flash before your eyes, and I remember having vague thoughts along the lines of ‘Is this what dying feels like?’ (Old emo habits die hard). Luckily, I got up and – aside from some minor-to-moderate pain in my leg – seemed mostly in working order, though slightly shaken up. Mr. Iceland did his public service by checking I wasn’t entirely dead, then drove off once I had moved from the road. Why the hell did I get up and walk instead of, say, going to the nearest A&E department, or just going home and sitting with an ice pack on my by now entirely bruised leg? I honestly have no idea. After hobbling my way to the cinema, I ended up having to pay for both tickets, as my date – despite being much, much posher than me - had apparently drained his entire bank account that week. Worried that my leg would seize up over the next two and a half hours, I had to keep surreptitiously doing some stretches I remembered from a Tracey Anderson exercise DVD to check it was still working. It was all very romantic (that, and the fact that we were watching a film about a horse dying on the battlefield of World War One). Lesson learnt? Boys may come and go, but the Green Cross Code is forever.

The One Where I Paid For His Cab Home…Twice

I’d been on two dates with this guy that I’d met on Tinder. When we first started speaking, I initially thought that I had hit the jackpot: he had immaculate grammar when texting (which is very important), was really good-looking and seemed totally normal (or so I thought) in a pool of not-so-normal Tinder men. We got on really well during our first date, and I didn’t even mind when he insisted that we take it in turns to buy drinks. But then when it was time to leave, I ordered an Uber to take me home, and he got in, asking if he could share the taxi (even though we live nowhere near each other). When we pulled up to his flat, he jumped out without offering to pay for his fare. At first, I wasn’t that put off - until the same thing happened on date number two! I mean, I’m all for going Dutch, but when I’m having to pay for YOUR cab home – boy bye.

The Karaoke Fail

TBH I’ve never been big on the whole ‘dating’ thing. Something my friends and family have pointed out many a time (Alright, alright I GET IT!) That said, this probably stems from an awkward encounter I had at university, which try as I might, I will never forget. When I was 19, I went on date with a French guy I had met in an East London bar days before - but didn’t really speak to all that much. 1.) He was from Paris and my shallow teen heart obviously translated this as automatically ‘deep’, intelligent and romantic and therefore great date material 2.) He was a musician. Sure, I’d never heard him play anything, but his guitar was glued to him and that was good enough for me. That was until we actually went on a date to Gordon’s Wine Bar and in the height of summer, tons of people outside the cosy joint, he burst into perhaps the worst rendition of Arctic Monkeys ‘I Bet You Look Good on the Dancefloor’ I’ve ever heard. No warning. And he kept forgetting the words and looking to me like ‘C’mon you know the words’. That is one duet I will never partake in, soz.

The One Where There Was Pus

I hadn’t seen the guy in years, but we’d had a few dates back then and stayed friends on Facebook. I’d just been dumped so when he asked me to go for a drink, I said yes. We were only meant to be having a quick coffee but he immediately launched into a rant about how terrible his life was now. He'd lost his job, tried to ‘rebrand’ as a comedian, which didn’t work out (I think because he had no sense of humour at all?). Then he’d broken his leg, which got infected. There was pus he explained, and did I want to see it? And oh - here it is. It was rancid and smelled awful. Then he made me go to Sainsbury’s with him to help him carry his groceries. Needless to say I wish I'd never met up with him.

The One With Road Rage

I was at University. We met in front of the student union as he was trying to get people to sign up for mailing lists, and some how I ended up signing up for a date. A Sunday afternoon meal and walk in the park. Skip ahead a couple of days and I’m late for an important lecture and I had to floor my 1.1 Kia Picanto after my spa treatment ran over. As someone rushed in front of me, I screeched to a halt, beeping my horn manically, as a collision was imminent. I lent out of the window screaming “LOOK WHERE YOU’RE GOING IT’S A ROAD, IT’S FOR CARS” only to see my date, standing inches away from my car and peering in and laughing. I tried to seem cool and calm, with my car halted in the middle of the junction. "Oh hey, it’s you again…” I said, winking, before quickly parking my car and letting the world swallow me up.

The One With The Walk Home

I'd just moved to Manchester, the dodgy end, and I'd also met a lovely German guy. We went on a date and he wanted to walk me home after I'd made a lot of fuss about the area I lived in. As we turned the corner the street was lit up with blue flashing lights. The sirens were echoing off the Victorian brick walls and in the distance I saw police tape flickering in the wind. As we edged closer, my fingers gripped his tighter as I realised that the tape was wrapped around my house. And the sirens were calling out to me! He thought it was hilariously coincidental until I said: “Sh*t. That’s my house.” But being the gentleman he was, he walked me to the Police who insisted that “crossing a crime scene was against the law” and that I “wasn’t allowed in until the crime scene investigators had ... investigated.” It turned out a man had been stabbed on my doorstep. A gang had been chasing him and he ran up to our house to try and get in but no one had opened the door quick enough. The guy took me to stay at my friends, but I never did hear from him again…

The One At His Parent's House

I met a guy while rather wasted on a night out in a cheesy club – and should have known it wasn’t going to be a match made in heaven. He was wearing a shark tooth necklace for starters. But his Gap Yah tendencies couldn’t have prepared me for our first date at his house. Assuming we’d meet at his and then head to a pub, I turned up to a massive ten bedroom house – it was so posh it had an antique toilet. And I thought ‘What kind of guy his age owns a house like this. Is he dealing drugs?’ or 'Is he the Mark Zuckerburg of North West London?' All became clear within the first five minutes of the date (after he’d heated up some leftover bolognese for us) when his parents walked in, who obviously a) owned the home, and b) thought we’d be dating for a long time. So they started talking to me like I was the long-lost girlfriend – showing me pictures of their holiday, chatting about their son – it was seriously weird – although they were an absolute delight. I got on better with them than the date if I’m honest. Said boy then took me upstairs to his very teenage bedroom, and talked me through the photos on his wall, and showed me his piano. He even started playing it for me. By this point I had nearly lost it over the teenage weirdness of the whole date, and I didn’t know what to do... So I ended up having sex with him... On the piano. And then, I ran out of the door approximately 10 minutes post-coitus, sneaking through the hallway so I wouldn’t bump into his parents again.

The One With The Revenge Story

We'd met on Tinder and though we'd got on well there was something holding me back from pinning down a date. But after two cancelled meet-ups I'd agreed to drinks - cocktails. When I arrived I was relieved - he looked nice and had a drink ready for me. We chatted away for a while until he got onto his recent flat move. He hated where he lived but he'd had to move fast as fast as possible, he said. It sounded dubious, so out came the journalist in me, and after a lot of probing about why he'd moved so swiftly, the story came flooding out. "You can't judge me, but..." he began. I'd already judged, of course. It transpired he hadn't got on with an old housemate who'd been hitting on his ex. So he'd taken drastic measures, and I mean drastic. On a whim one night on a walk home he'd passed a butchers and volunteered to take some end of day off-cuts home. Said off-cuts were two pigs heads, which he'd put in his housemate's bed for him to find on his return home. His landlord had thrown him out shortly after. I felt like I was on a date with a member of the mafia. However I was too scared to leave swifly... So I stayed for two more drinks. When he text saying what a great night he'd had and asked me for more drinks I said we'd had no chemistry. Luckily he never posted me anything scary. Good job I didn't give him my address.

The One Where He Cried In My Mouth

It was a blind date, friend of a friend situation. He walked into the bar, smiled at me, then started crying. His dog had just died, he said, and he really needed a drink. I felt so awful for him, I bought him a double whiskey and we spent the next two and a half hours talking about ‘Jez’ and looking at pictures of him. I thought getting off with him would help (stop him crying at least) but when I tasted his sad, salty tears in my mouth, I knew I’d taken a misstep – on this date and in my life.

The One With The Bathroom Window

I'd been on a few dates with an Australian guy and I was instantly besotted (which never ends well, does it?) After the third date I had started getting loads of butterflies just talking about him, and after our date I ended up staying around his house. Nothing happened during the night, and I was still trying to act cool. Well, we all know that every cool and awesome day starts with having a cool and awesome shower. So off I went to take a shower in his bathroom. And I find myself looking in the mirror giving myself a pep talk while he’s pottering away in the kitchen making freshly squeezed orange juice. After telling myself how cool and awesome I am I thought to myself: “ooh it’s a bit chilly” and as I tried to make my hair look elegantly dishevelled I thought “let me just close the window”… And with that I jumped into the shower and start lathering up ALL the shower gels and making a bubbly foam beard and then I hear a loud BANG. I turn around to see that I did not close the window properly and it had in fact blown open and smashed against the wall outside. So foamy, elegantly dishevelled and completely, and utterly embarrassed I creep out of the bathroom in a towel and have to go fess up to the guy - who technically - is still a stranger of sorts, that not only did we not sleep together, but I’ve left you with a hole as a bathroom window and it’s zero degrees outside. But thanks for the orange juice and wait -you’ve just made fresh coffee too. Fk. Fk. F**k. Surprisingly we had a few more dates together before it all went to pieces, much like the bathroom window.

The One Where He Was Wasted

We’d had one date (Tinder □) and I wasn’t really feeling it, but he was really pushy about meeting up again. I agreed to a cinema date (because: less talking) but when we met up for a pre-drink he was absolutely plastered and insisted we stay in the pub. He could barely form a sentence, and at one point he tripped up over his seat (I don’t even know how, he was literally sitting on it) and just lay on the floor for a few minutes. Then he asked me if I had a ‘stylist’ and when I said no he asked me why I ‘didn’t want to be happy.’ Then he took his purple trainers off and put them on the table. To… demonstrate… happiness? I told him I had to leave and in his enthusiasm to kiss me, he knocked someone else’s entire drink into my bag. I found a cocktail umbrella in there the next day.

The One Where We Ended It

It was probably date number 10 and we had had a bit of a time out because I was really unsure whether we were right for each other. He had strict rules about the roles of women and I… did not. But we met back up to give it another go in a beautiful restaurant that overlooked the Thames (near his apartment that also overlooked the Thames), but all we did was bicker at dinner. There was an awkward silence over dessert and I was thinking to myself to just get it over with politely - thank him for dinner and then get in a cab and never look back. However, I never got the chance to politely finish anything because when I thought he had gone to the bathroom he had actually got up, paid and left. And it was only 15 minutes later when the waiter came up to me and asked: “Excuse me, has your date left you?” that I had to make my excuses, and walk calmly out of the restaurant. I called him to ask what the hell happened and he said that because we hadn’t said anything to each other in five minutes, it was obvious we had nothing more to say to each other. And so, we never did.

The One Where He Wasn’t As Advertised

We’d matched on Tinder (ditto the above) and arranged to meet. We’d chatted a fair bit and he seemed like a nice guy and pretty funny, but we’d not gone as far as switching Facebook names or Instagram. Looking back, this was my first rookie mistake. The second was meeting for dinner – never a good move on a first date as it takes a minimum of an hour and a half – but I still turned up excited to meet him. There was just one catch. He had no teeth. When he smiled at me I was completely taken aback – we’re talking like max two to three teeth max. I awkwardly sat through one very hurried course before rushing home to check his Tinder profile again. He hadn’t been smiling with his mouth open in any of them...

READ MORE: Idris Elba Could Be Your Valentine's Date

READ MORE: 26 Things You'll Know If You're The Only Single Girl In Your Squad

Just so you know, whilst we may receive a commission or other compensation from the links on this website, we never allow this to influence product selections - read why you should trust us