Dating : Worst First Dates… & What Happened Next

Sometimes clichés come into existence because there is simply no better way to describe a situation. So when we write that modern dating is an absolute minefield, you’ll know it’s because meeting an absolute tool is a very real danger many of us face.

More people than ever are navigating this treacherous ground thanks to the rise in dating apps and online agencies that allow you to “match” with people you’ve never met and arrange a blind meet-up in the vain hope that they might be able to hold a conversation without doing anything weird. One false swipe and we risk losing our minds, our cool and our dignity on a humiliating night out with someone totally awful. And paying for the privilege, too.

Of course, this isn’t always the case, and like any game of roulette, there is a chance it’s all going to be fine. You could be one of the many people who meets their life partner through Tinder, if that’s the sort of thing you’re aiming for. You could, according to this 2017 study, end up having a happier relationship with someone you met on Bumble or Happn than anyone you encounter in real life. You could wind up with that great night in bed you’ve been dreaming of for ages without any red flags being waved whatsoever.

Or it could be completely terrible.

On the bright side, so long as you are safe and well, bad dates tend to make for better stories. To demonstrate this, we asked nine women to share their most dismal dating disasters, from the blind drunk model who sulked when he couldn’t smoke heroin in the cinema, to the holiday home sweetheart who stood back and watched while his date rescued drowning children. They really are quite something.

Marie, 26

I met this model guy at a party who had just finished walking in Paris Fashion Week. We got on super well, snogged a bit, and at the end of the night he took my number. The next day he texted and suggested we go to the cinema together on Tuesday afternoon.

We met at around 4pm in Soho, London. He was pretty late and also blind drunk. He explained to me that he’d just come from a photoshoot where he had to ride a motorcycle topless and couldn’t possibly do it sober.

Then he said: “Oh, the movie starts in about an hour. How about we go and get some heroin?”

Now, I’m hardly a prude but this was taking things a bit far. I said no, expecting him to move on pretty quickly from the idea.

“Oh come on, my dealer’s around the corner,” he begged. “We don’t even have to inject, we can just smoke it in the toilets of the cinema.”

I still said no and he started sulking.

Instead, we bought a cheap bottle of wine and sat drinking it in silence outside the Prince Charles cinema. When we went in, he asked the counter girl for the cheapest movie they were showing (very romantic). It turned out it was this three-hour long sci-fi movie from the ‘70s.

He’d brought a bag of pickled onion Monster Munch, which he ate while waiting for the movie to start. We sat down — him completely pissed and stinking of pickled onion — and he immediately tried to make out with me. I pushed him away, and he started to move his hand up my thigh instead. I stopped him doing that, too.

Then he passed out on my shoulder, where he proceeded to snore for three hours while I was forced to watch this awful movie with no discernible plot.

I still went on a second date with him.

Hannah, 31

I met this guy at a party over Pride weekend. We got on really well at the time, and shared an interest in films. We exchanged numbers and chatted casually over text before he asked me out on a date.

We went for dinner in a restaurant, during which he drank an entire bottle of wine to himself and we only had starters.

He then proceeded to show me pictures of people being fisted at a sex festival, while describing in graphic detail the time he’d had sex with a lesbian.

I called him out and said I was uncomfortable with him showing me these images. He responded by asking if I was easily offended. So I called him a creepy sex pest and left.

Later on he sent me a stream of drunken messages apologising and saying he needed to assess his actions.

I sent one back saying, “Okay, have fun!”

Needless to say, there wasn’t a second date, or any further discussion about films. It was pretty clear the ones he wanted to be watching were not the same ones I did.

Sam, 36

I have quite fine hair and naturally fine eyebrows. In a way it’s a bit of a gift as I never need to pluck them or have them groomed, they just are how they are. I’d never been particularly conscious about them, until I went on a date with one particular guy.

The very first words that came out of his mouth when he saw me were: “Did you pluck your eyebrows like that just for me?”

I don’t know if he was trying out a negging technique or genuinely thought that was an okay first thing to say to someone but it killed the mood pretty instantly for me.

Perplexed, I responded: “Erm, no, I just have really fine hair?”

“Oh, phew,” he replied. “I thought you’d made them really small just for our date — because they won’t grow back, you know.”

I stayed for a drink, during which he turned the conversation back to my eyebrows not once, not twice, but five times. At which point I just got up and left. And spent the rest of the evening looking in the mirror wondering what the hell was wrong with my eyebrows.

Louise, 42

I’d met Garry through a friend who worked with him at a holiday home in Wales. On our first date we decided to go down to Porthcawl beach for a romantic stroll.

Things were going really well until I spotted two small children struggling in the water just off the coast from a cluster of rocks. Being a strong swimmer and knowing what I was doing, I jumped into the sea to rescue them.

He, on the other hand, stood there and watched.

I ended up getting torn to shreds on the rocks trying to keep these kids above water while we waited for the lifeguard. When the lifeguard arrived, he jumped in after me thinking I’d made a suicide attempt and not seeing the two children either side of me.

Thankfully, we were all fine. Garry in particular as he hadn’t done anything. But the date did end with him having to hold my skirt up while a paramedic treated cuts on my bum cheeks.

I was mortified. But I was also a hero.

We actually dated for two years after that.

Rachel, 24

I went for a beer and a pizza with a lad from Tinder. He was charming, sweet, funny and the food was great.

Everything was going really well until he made some really off-key, awful comments about two people who walked past the window of the place we were in — a drag queen and an old school rocker.

I couldn’t believe anyone could be so nasty about people they’d never met. Little did he know, however, that they were actually both friends of mine. I confronted him about what he said but the pizza was so good, I decided to finish my food before leaving.

I shouldn’t have bothered. His next smooth move was to tell me about his amateur photography skills by showing me all the incredibly explicit photographs he’d taken of various girls over the years. Now, I’m an art graduate, and used to nudity and sexual expression. But for a first date? It had all gone too far.

I asked him what he was trying to achieve, but left the door swinging behind me before he had time to answer.

Nicole, 24

I went on a first date with a guy, let’s call him Chris, a few years ago.

He seemed okay at first, and we were in the middle of a conversation about TV shows. He’d never seen Game of Thrones and I started trying to explain some of the plot to him. Obviously, there’s a lot of nudity in it and some fairly explicit scenes.

Reader, he laughed every time I said the word ‘sex’. Like a small child.

“He he he, you said the word ‘sex’!” he said, and proceeded to lapse into giggles.

Safe to say, there was no second date.

Tristan, 29

I came into contact with Simon via a dating app. There were no real red flags waving in my direction while we were getting to know each other via messaging. He seemed full of life and actually quite witty, which is a big plus for me.

When I met up with him, the first thing that struck me was how strange he appeared. There was something distinctly chilling about him, and I started to wonder if he had skin-wearing capabilities. Or was a murderer.

The first thing he said to me was: “You look like your pictures so I’ll buy you a drink.”

Charmer.

I laughed, but he just stood there and stared at me blankly before turning to the bar to order.

Introductions out of the way and drinks in hand, the conversation turned to what seemed to be his favourite topic: him. He proceeded to boast about his supermodel ex-girlfriend who hated having her photograph taken, which was apparently why there were no photos of them together.

It wasn’t long before I got my friend to rescue call me so I could loudly pretend I had to be somewhere else — and fast.

As I was making my escape, he asked if he could see me again. I didn’t answer and so he shouted after me: “Next time we’ll get so fucked up, you’ll end up in hospital!”

Romance, it seems, is not dead.

Claudia, 38

My worst dating experience is a bit different from all the others, as we didn’t actually ever meet.

I’d messaged this guy to see if he was still up for meeting for a drink at 8.30pm that evening near where we lived in Liverpool.

He texted me back to apologise and asked if we could rearrange another date. He suggested we meet between the hours of 7am and 7pm.

I couldn’t make it that early during the week because of work. So he offered another date… in 12 weeks’ time.

It took me a while to work out why he was being so specific about certain times until he admitted it was in keeping with a court order he’d just been given. He’d been fitted with an electronic tag and was under curfew.

I’d already moved on by the time it was removed.

Radisha, 23

I’d been messaging Craig back and forth for a while on Tinder. He was a stockbroker, American, and worked from home most of the time. From his photographs, he was extremely good looking, and we got on really well when we spoke on the phone.

He lived in another part of London to me, and we’d arranged a date to meet somewhere in the middle so we could both get home okay. A couple of hours before I was due to get to the bar we’d decided to meet at, he said he had been stuck on a deal and couldn’t leave his house for at least another hour. He suggested we go somewhere near his and I agreed, even though it was a fair way away from me.

London being London, it took a few minutes longer to get there than I’d anticipated, and I texted ahead to tell him I’d be five minutes late. I didn’t hear back from him, and when I got to the pub, I couldn’t see him anywhere. So I grabbed a glass of wine, took my book out of my bag, let Craig know I was there by text and sat and waited.

And I waited. And I waited. Until it clocked on to an hour, and I still hadn’t heard back.

Feeling pretty annoyed at that point, I decided he wasn’t coming and left for the station to make the long journey home.

As I was about to board the train, I got a message from Craig.

“Sorry, I can’t stand lateness,” it read. “It’s just so disrespectful. I left after two minutes.”

I sent one back asking him why on earth he’d left it an hour before telling me.

And he bombarded my phone with calls and messages, begging for forgiveness and asking for a second date.

Alarm bells well and truly hammering, I said no. So he sent me the word ‘Fuck’ one hundred times.

I did not respond.