Best date stories: romance, hilarity and disaster

Image by the brilliant Stuart F Taylor

Recently I asked you all to tell me your best date stories – the funny ones, the lovely ones, the disastrous ones, and everything in-between. The winner would receive a night of free drinks courtesy of my sponsor Every Cloud Bar. You came through spectacularly, with some incredible dating stories. Read the entry that won, check out some of the other amazing stories, and share your own in the comments if you’d like to join in…

Best date stories competition

Firstly – huge thanks to everyone who entered. It was really tricky picking a winner because there was such a brilliant range of funny/sexy/weird/romantic to choose from.

And thanks to my sponsor Every Cloud Bar, for providing a free night of drinks to the winner! If you didn’t win (or you didn’t enter) but you’d like to go on a fun night out in London, I can thoroughly recommend taking your next date (or your pals) to the bar. They do amazing cocktails (try the bramble + chilli one which is quite superbly named You Can’t Bramble The Truth and is fucking awesome), are super-friendly and they also have some special GOTN-related presents for you.

The first two people to go in and tell them ‘Girl on the Net sent me’ will get a super-limited-edition GOTN badge. And seriously, please do: it’s a helpful way for me to show them just how powerfully influential I am, that I can bend people to my nefarious will and get them to go and drink cocktails at a neat little bar in Hackney.

Meanwhile, entertain yourself with these fantastic date stories. Starting with the winner, written by the fabulous 19Syllables… Can you tell that I’m a sucker for romance?

19Syllables’ date story

I’ve never been on a date. Written like that it seems pretty tragic, but it’s not as bad as it sounds. I’m from the days before dates. Back from the times when people found partners and hook-ups by going out as a crowd, intersecting with other crowds, letting things get a little messy and seeing who came out of it all the most fun. We knew the word ‘date’, but it was something reserved for Americans on TV or in high school films filed away and ring-fenced with other words like ‘prom’, and ‘rain-check’ and ‘drive-thru.’ I know some couples in long term relationships often operate a date-night system to keep romance alive, but it’s not a thing we’ve ever done. Our love was founded on the old “go out and let things get a bit messy” model; it’s what we know and it has served us well, so that’s pretty much what we still do. It’d go something like this:

“I fancy cocktails.”
“Good idea, I’ll pump the bike tyres up, while you zip upstairs and put your leather skirt on.”

We had something that felt like it was going to be a date one day last year. I’d won tickets to a play so, I rung him up at work.
“I’ve won some tickets to a play tonight, do you want to come?”
“What’s it about?”
“It’s at The National Gallery, it’s about Rembrandt.”
There was a silence…
“That sounds shit.”
I think I blinked a few times before replying, and then I said:
“These are free tickets, I am lovely, I’ve rung you up at work, asking you out on a date. I’m going to hang up and call you back in a couple of minutes. Let’s start this conversation over again.”
“OK sure.”
I called him back.
“I’ve won some tickets to a play tonight, do you want to come?”
“What’s it about?”
“It’s at The National Gallery, it’s about Rembrandt”
There was a silence…
“That sounds fantastic, so exciting! I’ll meet you at Charing Cross at 7, let’s have dinner afterwards!”

After the play, as we walked across Trafalgar Square he said I’m sorry I was an arse on the phone, it’s just that sort of thing is not usually my bag and I thought you might have preferred to go with Jen or Caro or someone – someone that you more usually go to the theatre with.

“Yeah I rung both of them up but they couldn’t make it on short notice.”

“What? I’ve been feeling guilty about fucking up the date-night conversation but I wasn’t even the first person you asked? Not even the second person you asked!”

It was true. I’d pulled the “I’m going to put the phone down and start this conversation again” card and yet, love him though I do, he wasn’t really the person I’d really wanted to go with. Also, he had been doubly right; the play, about Rembrandt, had been a bit shit.

We sniped and hissed at each other as we pushed through the Trafalgar square tourists, alternatingly smiling and polite to them (”Excuse me, would you mind?” “No, no that’s quite alright”) in the sing-songy way of English people negotiating others, and grizzly with each other in the low level, side-comment way that can only be finessed by people that have known each other for decades. (“I dashed all the way over from bloody Camden to sit through that” “I can’t be held responsible for how much you liked the play.”)

We slipped into a cocktail bar just off the Charing Cross Road, still both slightly aggrieved but agreed to call a truce and make the best of the second part of the evening. I made a mess of getting onto the bar stool in a ladylike manner and he giggled, giving me that sideways knowing, half-smile that he has, and a hand to steady me. In that moment I think we both recognised the ridiculousness of it. I leant into him across the chasm between our bar stools and put my head on his shoulder.

We had a couple of cocktails there and then wandered up into Soho where we let things get a bit messy to see who came out of it all the most fun.

It was him. It’s always been him.

Other fantastic date stories

[Most of these are in snippet form – click the links below each story to read the full thing. I promise you will not regret it.]

We met in Summer Camp, went on a date to the nearest waterfalls. We drank in the sun, me stripping down to my bikini. I could see his erection get bigger. I invited him to the forest and ‘accidentally’ rubbed myself against him while we got changed. We fucked outside the staff treehouse that night, shooting stars overhead. He told me he loved me the next week.

We’re engaged to be married 3 years later.



London is great when it’s sunny. On a grim, wet November evening, when you’re standing in the rain in Chinatown, waiting for a date, it’s not so great. When your date is an hour late, with no message, it sucks…

Read the full date story by ‘not my real name’


I was still at University, and me and my girlfriend had been on a date or two. Nothing serious, but we’d clicked.

One morning I woke up and went to the shared kitchen and hunted for last nights dinner, or milk for cereal. I came up short. I was texting my Girlfriend as I did this, and I sent what I now realise was a rather weighted text. “Do you want to go out and get some food?”

We went out. To Sainsbury’s.

Read the full date story by ‘Mark’


…Conversation has been a little stilted but on the whole I’ve been enjoying myself. As we get close to the pub, I start to feel odd, the inside of my ears start to itch, my skin breaks out in hives and I start to find it difficult to breathe. An ambulance is called, I’m having a severe allergic reaction to something. (I’ve never had one before). The ambulance arrives and I get in, he comes too and the paramedics start joking about how “it’ll be a great story to tell the grandkids”. They inject me with adrenaline and the start faffing around to find a vein. At which point he turns very white and admits to a needle phobia.

Read the full date story by ‘AC’


I sit opposite him for the thousandth time, watching his gentle hands turning the glass as he details the ways she is once again breaking his heart, despair running rich in his eyes, I sit opposite, putting the pieces back together, hoping for the thousandth time that a piece of myself will stick

By The Quiet One


This is the story of how I learned I shouldn’t always push past chronic fatigue. Sometimes, the best thing to do is postpone the date, again, and curl up in a duvet with a mug of tea and definitely only talk to people who know me well. But, I’d already had to postpone twice, and we’d already exchanged a lot of filthy text messages, and I can only be sensible for so long before the desire for first-date kisses (tentative, learning, exploring) takes over.

So, I went to meet the guy. I blithered my way onto a train and sat there, hoping I wouldn’t feel quite so thick-headed once I got there. It’s happened before – I’ve felt bloody awful and then as soon as I’m with people I like being around, I rally just enough to turn into a decent approximation of a human being, rather than a dribbling meat-sack. We can all hope, can’t we?

Read the full date story by ‘Alice’


We get a drink and sit down, general small talk ensues, then he comes out with “what are your thoughts on taxidermy?” – now I’d already said I had been a vegetarian for years and spoke about how I don’t believe in hunting as a sport etc so I’m not sure exactly what he thought my response would be- next thing “I do taxidermy in my free time, I have a crow on my bedside table, his name is Colin & he’s my best friend”, this is followed by some mild nervous laughter on my part- surely he isn’t being serious?!

He then proceeds to show me photos of him & Colin together, (there’s a lot of them posing like an awkward comedy double act/ bad 80’s cop show duo), “I’ll show you how I stuffed him” he says then continues to try show me particularly graphic photos and videos of him doing this exclaiming the odd phrase such as “this is me scooping his brains out with a cotton bud” and “I pushed my finger in too hard there so had to sew his chest back up- look”.

Read the full date story by Crawf


One of the other temps and I started hooking up. Literally, booty calls in their purest, most stripped-back form. If one of us was horny, or pissed, we’d text the other, end up at one of our flats, have pretty mindblowing sex, then get up and go to work the next morning.

This was all fine and good (I mean, it wasn’t, I completely fell for him, but that’s a whole other story) until one time we accidentally hooked up on a Friday instead of midweek. I woke up in his bed on a sunny Saturday morning, head throbbing, throat parched, with the entire day stretching out before us. I had nowhere I needed to be. And no idea how to deal with that.

Read the full story by fionachadd


I had pre planned a natural ending to the date in that I was going to the theatre that afternoon with a friend. My date ended up accompanying me to the theatre and, ultimately, queued up to try to get a ticket too.

Thing is, this was for a quite dark and intense play about virtual reality, paedophilia, and murder.

Read the full story by Charlie Forrest


He came back to ‘mine’…mine being an airbnb flat, which is where things got tricky. I’d booked the cheapest place I could find, and it was lovely, but it was only cheap because I was staying in the attic, so had to ascend and descend a very loud and rickety ladder to get in and out of my room, which caused so much noise when we both went up, I’m convinced we woke up the entire house. Other highlights included having to rifle underneath piles of flyers with my own face on to find some condoms, and him finding the house instructions my host had left me (including about house guests) and telling me, faux-sternly while waving them at me, “I don’t want to be a narc, but I think we might be in contravention of the rules.”

Read the full story by RB


I invited him to a play at a small local theater where the stage was in the middle of the audience. We were in the second row. Soon after the play started, I noticed an itchy tingling tickle between my breasts. I thought maybe it was a stray hair at first so tried to shift position. The stage light spilled out onto us and it was a first date. I didn’t want to just reach my hand down my cleavage in front of everyone.

When shifting position didn’t work and I felt more tickling, I realized with dread that a bug must have flown into my shirt…

Read the full date story by Maria Sybilla


I was your standard enthusiastic, affable but utterly useless styoodent, all ill-advised long hair and a lumberjack shirt. Cos in the 90s, if you weren’t wearing a lumberjack shirt, it was actually illegal for you to say you liked Nirvana and Pearl Jam. And that way led to being sent to study in Coventry, not Up North, where this story takes place.

She worked in the same pub as me, drank pints, played darts and wasn’t a student. She was an archaeologist. Probably still is. She was a riot.

And it was on. Always had been. Like Donkey Kong.

We met ‘accidentally’ in our pub and proceeded to get gale-force drunk.

Drunk led to…


Told you I was useless.

She then had the splendid idea of going to one of the university archaeology buildings to show me a cool thing.

So we took our £2 pizzas and an argument about pineapple (it’s ace) to a musty basement in a dark building.

A basement full of ancient disinterred skellies. Two or three hundred of them.

The was more booze.

Then, as I stood there with a slice of hawaiian in one hand and some poor bugger’s skull in the other, she dropped to her knees, said, “You don’t mind, do you?” and sucked my cock.

Read the full date story by BarelyLouchid

I hope you enjoyed reading people’s best date stories as much as I did. And hopefully you will now understand why this last week I have been receiving DMs from friends trying to influence the vote that just say ‘CROW. THE CROW.’ Honestly it was really hard to decide a winner, and I wish I could give prizes to you all – thanks so much for joining in with this comp and sharing your stories with everyone! 


  • SweetTheSting says:

    That’s an ace date story. From grumpiness to loveliness.

  • SpaceCaptainSmith says:

    I’ll have to read through these another time (though the winner was good). But for *bad* date stories, nothing is likely to top the one that was doing the rounds on the Internet the other day, about the poor girl who for some reason threw a turd out of her date’s window, then got stuck retrieving it, requiring the fire brigade to be called…

    • Girl on the net says:

      Haha yep! I can’t quite understand the mindset that brings someone to throw a poo out of the window, but it sounds like the GoFundMe has made more than enough to fix the window and donate some £ to charity, so I guess … good things happen to those who throw poo out of windows and then get stuck??

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.