My Ridiculous Tinder Date

Shortly after somehow surviving South America, I rediscovered this short story I wrote in 2016, about my one and only experience of Tinder. I wrote it as if it was fiction, but in fact it’s almost entirely a true account of what happened that night. Lulu and Rose’s names have been changed.


“Right. Show me.”

Lulu was in full business-like mode, and it gave me cold feet. Was this embarrassing? Was it intrusive? It was too late now: she was beckoning for my phone.

Sheepishly, I brought up the dating app onto the screen and handed it over. I took a swig from my pint for something to do, and awaited her judgement.

“Nope,” she declared. “Your pictures aren’t good enough.”

“They’re the best I’ve got,” I said, stung into defensiveness. Why had I chosen to ask advice from Lulu, of all people? I wanted a sensitive critique, and I knew she was going to be brutally blunt. What if someone in the bar overheard this conversation?

“You must have better ones,” said Lulu. “There are too many girls in your pictures, and you don’t look very good in them.” A couple of thumb-swipes and she’d deleted two of my profile pictures. Pictures that I had agonised over. It was stupid, really: I wasn’t sure I even wanted to go on a date with some stranger off an app, but at the same time, I was desperate not to sell myself short.

“Hey!” I said hotly. “You can give me advice, but it’s still my account!”

I made a grab for the phone. She held it out of my reach, tutting at me as though I was an errant child. “And rewrite your bio,” she said, shuffling down the sofa away from me.

“What’s wrong with it?”

“The whole thing, Ollie.”

What’s wrong with it?

“Look, why don’t you just say ‘I always stand on the right on escalators’?” Lulu suggested.

I stared at her, bemused. “It’s not funny and it’s not true,” I said. “It’s not me.”

“Look, Ollie,” said Lulu sternly. “I have two hundred and thirty seven Tinder matches. How many do you have?”

“Two,” I conceded. “But I’ve only had it for about two days –”

“Three,” said Lulu. “You’ve got three matches.”

I snatched at the phone again, almost spilling my beer. “Let me see!”

Once more, Lulu held it away from me. “You can look at her afterwards,” she said.

My shoulders slumped. “This is a bad idea,” I said. “I don’t want your help.”

“Well, you need my help,” said Lulu, swishing her hair back over her shoulder. “Let’s sort out your photos. Put your best one upfront, then one that shows you having fun, then a sexy one. There’s a formula.”

“A sexy one?” I groaned. “God help me. You’re not going to find a sexy one.”

“Let’s have a look then,” said Lulu. Then, a moment later: “God, it’s true – you don’t have many good photos.”

But I realised her guard was down, and I had had enough. I plucked the phone from her hands and stuffed it into my pocket. “Forget it,” I mumbled. “Bad idea. I’ve had enough.”

We glared at each other for a moment. Then she sighed and rolled her eyes. “Well, I tried,” she said. Picking up her wine glass, she sipped slowly, and I tried to work out if she was sulking.

“So who’s coming to Cam’s thing tomorrow evening?” I asked, trying to change the subject. Cam was on the same university course as me and Lulu, but she lived in Oxford, so we didn’t get to see her in London much. I was looking forward to catching up with her.

Lulu paused, possibly deciding whether or not she was irritated with me. But I got the benefit of the doubt. “I think Oscar, Sophie, maybe Cam’s girlfriend,” she said.

“Did she say any more about what the event is?” I asked.

“Her friend Bob is performing in the show,” said Lulu. “He’s new to the drag-queen circuit so Cam says he’s nervous. So the more support the better.” She downed the rest of her wine. “I’m getting another drink.”

As soon as she had got off the sofa and headed for the bar, I pulled my phone out of my pocket. I wanted to see who my third Tinder match was. The app was addictive: I somewhat regretted having downloaded it in the first place.

I had matched with someone called Rosanna: a pretty redheaded twenty-year-old, who was accompanied in a couple of her photos by a fluffy dog. It looked a bit like my family’s dog, Button.

Rosanna’s pictures contained no cleavage, no swimsuits, no photos from drunken nights out. She was in possession of that rare thing: a classy Tinder profile. Not really knowing what to do, I sent her a brief, inane message about the dog and tried to push Tinder from my mind.



Tinder: Button and daffodils

The next day, I was walking Button around across a deserted rugby pitch near my house, when Lulu texted. “Cam says bring friends.

With the lead wrapped around my left wrist, I kept half an eye on Button and texted a few people. Two friends replied immediately saying that they couldn’t come; but two others, Tom and Harriet, seemed very keen.

Tom had been in my Eton boarding house. I wondered if the whole Tinder thing would have been easier, if it hadn’t been for Eton. For five crucial years, I’d been separated from female contact, and now I didn’t know what to do with the dating app now that I had it.

As I wandered beneath the plane trees, Button trotting nearby, a mad idea occurred to me. I chuckled to myself at its audacity, and tried to dismiss it.

But I had nothing to lose. What was the worst thing that could happen?

I walked on. We meandered away from the rugby pitch – I clipped Button’s lead onto her collar – and headed through the well-tended Fulham streets to the daffodil patch in the Hurlingham Club. My phone buzzed. It was Rosanna’s reply. It was friendly but brief – but it settled things in my mind. I was going to pursue my idea. Why the hell not?

It took me half an hour to craft my reply to Rosanna. “Listen – this is spontaneous and last-minute, but in the last hour I seem to have accidentally ended up co-organising a smallish group of friends to go to a drag lip syncing competition in Hoxton this evening. Why don’t you bring a couple of friends and come along – we pretend we’re old friends through some obscure connection, and the evening is guaranteed to be hilarious and relaxed. Entry is free apparently, and the whole thing sounds like a lot of fun. Which part of London are you based in?

It gave me a little thrill to send it – but I did not expect to receive a reply so quickly. Within five minutes, she responded. “Haha sure why not – I have a thing that doesn’t finish until about quarter past nine though.

I stopped in my tracks. At the other end of the lead, Button was jerked to a halt, and she turned around to see what the matter was.

I hadn’t expected Rosanna to actually say yes. I was just humouring myself, letting my imagination carry me away. It began to sink in that I had done something bold to the point of recklessness. Now I had to actually go through with it.

I replied that I was sure it was fine if she didn’t get there before ten. Now she and I had to come up with a backstory that would stand up to my friends’ scrutiny. We swapped phone numbers and coached each other over text. Rosanna, who was a first-year architecture student, had met me two years ago through a mutual friend, when she had come to stay on an imaginary trip to my university. She had recently returned from a year abroad in Canada, which conveniently happened to be true and also explained why she hadn’t met many of my friends before. We went over the details until we thought we might be able to pass as old pals.

One more thing,” she texted. “Don’t call me Rosanna – everyone calls me Rose.”

Christ alive, what the hell am I doing, I thought.




Lulu opened the door to her flat, wearing a towel around her hair. “I’m just putting my makeup on,” she said, not bothering to say hello. “Cam’s in the kitchen.”

“What about the others?” I asked.

“They’re not coming,” Lulu called as she disappeared into the bathroom. “They all bailed.”

“Oh,” I said, taken aback. Somehow it felt weirder if I was going to meet Rose with a smaller group.

“Yeah, those bastards,” said Cam, greeting me with a hug. “They all flaked out on us. Who else is coming?”

“Three of my old friends,” I said. “Harriet, Tom, and Rose. What about this friend of yours who’s performing?”

“He’s already at the venue,” said Cam. “We should head there nowish – it begins at eight.”

“It begins at eight? But my friend Rose says she can’t get there until ten!”

“I think that’s when it finishes, mate,” said Cam. “Come on, let’s get a move on.”

I opened and closed my mouth. Rose might not even get to see the event I’d invited her to. This was a disaster. What’s more, I hadn’t even had time to eat.

“Lulu, I’m taking two of your bananas,” I said, lifting them from the fruit bowl.

Lulu rolled her eyes. “Jeez,” she said. “Are you going to eat those in the street?”

“Yes,” I said.

“You’re ridiculous,” said Lulu.

“What’s wrong with that?” I cried.

“Nothing,” she said with her best patronising smile. “You do you, Ollie. Let’s go.”



Tinder: drag show
Genuine photo of the drag show

The venue in Hoxton turned out to be an overcrowded pub, and I had never been anywhere like it. Six-foot men dressed as princesses mingled with gaunt girls sporting tattoos, piercings and shocking pink hair. Everybody seemed to know everyone else, and I stuck closely to Cam and Lulu, trying not to stare at the barman’s leotard.

By now, I was in a state of high anxiety. Rose had messaged to say that she had failed to recruit any of her own friends, so she was coming to the event on her own. Furthermore, Tom and Harriet had inexplicably decided to have supper beforehand in Shepherd’s Bush, on the other side of London. Once they had realised how far they were from the event, they had apologetically dropped out. I was fuming but powerless, but I didn’t dare cancel on Rose – not after she’d actually agreed to meet me.

I also couldn’t let Cam and Lulu realise how stressed I was. I didn’t want to embarrass Rose by outing her as a stranger off Tinder – and I didn’t want to give Lulu the satisfaction. If Rose and I were going to go through with the pretence of being old friends, we were bloody well going to do it right.

The drag lip-sync competition was admittedly very entertaining, and Cam’s friend Bob gave an excellent performance dressed as a bondage-cat. But sure enough, it drew to a close shortly before 10pm. All I could think about was how I had invited a stranger off the internet to what was now essentially a first date in a drag bar, with two of my female friends in tow. She was going to think I was a nutter.

So much for the wonders of Tinder. So much for my clever ideas. If I told Lulu now, she would mock me mercilessly. Cam would probably join in, because to be fair I deserved it. There was no way out. Rose was due at any minute.

My phone buzzed. “I think I’m outside.”

 Oh bloody hell, here we go.

“My friend is here,” I said to Cam and Lulu. I pushed through the glittery crowds and stepped into the night air, feeling like I was in a very strange dream.

There she was: a short, slender redhead in a black leather jacket. She waved, dropped her phone into her handbag and gave me an awkward hug.

“Hi,” I said with a grin. “Thanks for coming.” The more I pretended that this situation was a bit mad but totally okay, the more likely it was that she would believe it.

“Am I in time for the end of the competition?” she asked. Friendly enough, but there was a formal note to her voice that told me her guard was up. There was something very proper about the way she held herself: straight back, knees together – everything about her, even her studied accent, made it seem like she had come straight from deportment lessons at a finishing school. I remembered that she was still only twenty: two and a half years younger than me.

“I’m afraid it just ended,” I said. “But it’s a fun pub and you can still see all the costumes, so let’s get a drink. I’ve never been here before,” I added, worried that she might think that the drag bar was my normal hangout.

Inside, Cam and Lulu said hello to Rose and didn’t ask any follow-up questions. Our carefully-crafted backstory was never tested.

Rose smiled politely at them and shook their hands. Then we both joined the drinks queue, which gave us a chance to talk.

“I’m so sorry,” I said quietly. “I didn’t realise it would just be the four of us…”

Rose was looking quite awkward and out of her depth, but bless her, she seemed pretty game. “It’s fine,” she said. “It’s an adventure.”

“I’ve never done this before,” I said. “I only got Tinder a couple of days ago.”

“Me too,” she said. I felt a wave of relief. She had nothing to compare this to.

When we rejoined the others with our drinks, I discovered time that talking to a stranger and talking to a friend are two very different experiences. Rose and I sat next to each other on a very squashy sofa – we had to lean on the armrests to avoid sliding sideways into each other’s laps. As we tried to chat as though we were totally at ease with each other, I was painfully aware of Cam and Lulu. I mustn’t let them suspect anything or this whole precarious evening would come crashing down. Rose, already struggling visibly, would be mortified if she was outed as my Tinder date. But at least she was my partner in the lie. In a strange way, Rose and I were a team.

And that meant Lulu and Cam were the enemy. It got much worse when Bob emerged from backstage, still dressed as a cat, and Cam went to talk to him and his drag-queen friends. Lulu was left as an unwitting third-wheel. The conversation faltered. Rose pursed her lips, keeping her legs primly folded as she gripped her armrest and tried not to slip any closer to me. I knew I was sweating.

Lulu started telling stories at my expense, as she so often did. She had an uncanny knack of making any innocuous little incident sound hilariously embarrassing. Rose was laughing, and as I forced a rueful grin I couldn’t tell if I was grateful to Lulu or if I wanted to strangle her.

Rose asked me a couple of questions about what I’d been up to recently. As I replied, I was aware that Lulu was being shut out of the conversation. But I really did not care. If Lulu sulked about it later, I would have to grovel. Right now I really, really needed to keep Rose entertained.

I wittered on, noticing that Lulu had grumpily retreated behind her phone. Rose was smiling and telling funny stories. Perhaps this wasn’t so bad after all.

At eleven, the bell for last orders rang, and at that moment Cam rejoined us. “Right, guys, I’m probably going to catch a night-bus back to Oxford now,” she said.

Lulu looked up from her phone. “I’m leaving too,” she said. “I want to go to bed.”

It felt as though Rose had only just got here. I rallied my courage and tried one last throw of the dice. “I’m not tired,” I said. “I want to go to a bar.”

“A bar sounds good,” said Rose.

I could have punched the air. Somehow this drag-bar situation hadn’t frightened her off. I must be doing something right – though I had no idea what.

The four of us walked to the Overground station and headed for Whitechapel. There, Rose and I said goodbye to Cam and Lulu, and got on the District Line without them. As the tube pulled out of the platform, I gave a big sigh of relief and grinned sheepishly at Rose. “Thank God that’s over.”

“That was completely ridiculous,” she laughed.

“I’m so sorry,” I said.

“It’s fine. They seemed nice,” said Rose.

“Lulu was on her best behaviour,” I said.




Rose lived in Streatham, so my idea was to find a bar in Victoria. From there, she could catch a train back home, and I could take a bus to Fulham. And Victoria seemed like a good place to find lots of bars.

As soon as we left the tube station, though, it became clear that I had made a major mistake. Victoria was, in fact, a terrible place to find lots of bars. Somehow it was midnight already, and Rose was watching me with anxiety and growing doubt as I searched and searched the internet for somewhere that was still open.

“We’ll find somewhere,” I said. “We will.”

“I do really need the loo,” Rose admitted.

Oh, bloody hell.

Rose had been relaxed on the tube, but now she was exhibiting the same stilted properness that I had noticed when we had first met. I didn’t have to be a ladies’ man to recognise that it was a bad sign.

I resorted to a more desperate tactic. Google Maps told me that there were a couple of nearby bars which closed at midnight. I led Rose to the closest one and banged on the door until the manager opened up, holding a mop.

“Yes?” he said, squinting at me and curling his lip.

“I’m really sorry, but do you know if there are any bars around here that are still open?” I said. Rose was standing a little way off, with her arms crossed, watching me.

“Nothing round here,” growled the man. “The nearest bars would be Soho.”

Soho! That was half an hour away on foot. Rose was still watching me. I felt humiliated. The drag bar had been enough of a cock-up – if I failed now, she would have every right to think I was an idiot. Would this night never get any easier?

“Excuse me,” said Rose. “Please can I lose your loo?”

“Sorry, no,” said the man, and slammed the door.

Then I had a lightbulb moment. It was my third streak of inspiration of the day. The first had been to invite Rose to the drag bar. The second had been to suggest that she and I should go to Victoria. If my current form was anything to go by, I should have been wary – but I was desperate, and in that moment I was just thankful to have a plan.

Once, after several drinks and a confusing sequence of circumstances, I had ended up on a strange night out in central London. I had tagged along with a friend, who had tagged along with his cousin, who had tagged along with his friend, whose father owned a casino in Hyde Park Corner. We’d all wound up in the casino, and we’d been signed up as members there and then. That was the only time in my life that I had been inside a casino, but I remembered that it had a decent bar. Most importantly, it was only five or ten minutes away.

“Tell you what,” I said. “I’m a member of a casino in Hyde Park Corner… It’s a long story. Let’s go there.”

“A casino?” repeated Rose.

“Yeah. It’s got a good bar. And there’ll be loos.”

That clinched it. Rose gave one last look at the train station – I was sure she was thinking about cutting her losses and heading home there and then – and followed me.



Tinder: casino
Appropriately hazy photo from the night of my previous visit to the casino

My mood was buoyed all the way to the Hilton Hotel of Hyde Park Corner, which I remembered was close to the casino. But at this moment the flaw in the plan materialised.

“Where is it?” said Rose.

“…It’s around here somewhere,” I said.

“I thought you said you were a member,” said Rose in dismay.

I felt as though Lulu was watching me in that moment, like some omniscient goddess, and laughing at me. I did not want to think what she would say when she found out about this.

“I’ve only been there once,” I said, doubling back along a street that had proved to be devoid of casinos. “The membership was free.”

“Well, what’s this place called?” said Rose, and there was a new edge to her voice.

Oh shit. Oh, bloody well done, Ollie.

“I – I can’t remember,” I confessed. “But I’ll know it when I see it.”

As we walked up and down the streets, I tried calling the friend who had been with me that night. He didn’t answer. Then I called the friend’s cousin. Again, no response.

I looked up at Rose and shrugged helplessly. She was almost hopping from foot to foot.

“Look,” I said, casting around for ideas. “We could go into the Hilton and beg them to let you use their loos.”

An expression of disgust crossed Rose’s pretty face. I was dimly aware that I was panicking.

I spotted a sign saying “CASINO.” “Maybe that’s the right one,” I yelped, heading towards it.

It wasn’t the right one. I was sure of that much – but I entertained some mad hope that perhaps it was a back entrance into my casino. The bouncer checked our IDs, searched Rose’s bag and eventually waved us through. Rose dashed off to the bathroom, and I stood in the middle of the bar area, looking around at the establishment I’d led us into.

Two words immediately sprang to mind: Dawning horror. I took in the framed photos of scantily-clad ladies wearing bunny ears; the empty plush booths all around me; the rabbit logo on almost every surface; the two bartenders and the bouncer watching me. I was in the bar of a Playboy Casino, and I was the only customer in the room.

My phone buzzed. It was Lulu. “We should go to more drag shows. Night x.”

It was tempting to phone her, to beg for help.

But there was nothing she could do.

There was nothing anyone could do.

I closed my eyes. I could be in bed by now. Instead I was… Oh god, how?!

Rose returned: back straight, skirt immaculate, leather jacket dangling daintily from her arm. She flashed me a smile. I swallowed.

“Rose…” I said quietly. “I am so, so sorry. This isn’t the right casino. This is the Playboy Casino.”

She stopped short and looked around in alarm, her mouth dropping open. She clutched at her jacket as though it was the only thing that might protect her.

We couldn’t walk out. The staff were watching us. Plus it wouldn’t solve the problem of where to find a drink. There was only one thing for it.

“I’ll get this round,” I said. “What do you want?”

“We’re staying here?” said Rose. Her eyes were now locked on the nearest, and most scantily-clad, of the photos on the wall.

“They wouldn’t like it if we left,” I mumbled. “I’ve cocked up. I’m sorry. Sit down and I’ll get you something.”

Rose pursed her lips. “I’m not sitting on my own, in here!” She led me to the bar and looked at the menu. “Can I just have a glass of the house white?” she whispered to me.

I looked at the price. £11, for the cheapest glass of wine? I swallowed.

The cheapest cocktail, meanwhile, was £14. “‘As fun and bubbly as the bunny who serves it,’” I read. “Do you think it’s really brought by a Playboy Bunny?”

“Don’t,” she said. Her tone was unmistakeable.

“Two glasses of house white, please,” I said hurriedly to the barman.

We sat in the corner, chewing the strange nuts that they brought us, casting around for conversation. We were both mesmerised by the garish design-scheme and the unsettling absence of any other customers. I thought I was prattling on, so I let the conversation lull for a moment.

“Keep talking,” said Rose. “I don’t want to think about where we are right now.”

Christ. Oh Ollie, what have you done?

Throughout our time in the Playboy Casino, I did not relax for a moment. How could I have let this happen? But very slowly, she started to see the funny side. Once more she relaxed, and by the time we left she was downright jolly. Thank God, the evening was over. I’d survived to the end of the night, she could hop on her train, and if by some miracle she wanted to give me a second chance, well, she had my phone number now.

We got back to Victoria station. The entrance was barred. We checked our watches. Rose had missed her last train.

Fuckety fuck.

It would take Rose maybe an hour and a half on night buses, a girl travelling all alone through Brixton in the middle of the night, to get home. She was not just stressed: she was fearful. There was only one thing for it.

“…D’you want to come back to mine?” I said. “There’s a spare room…”

Rose looked at me. But we both knew she was out of options. “…Alright,” she said.




I was slightly dazed as we boarded the bus to my house. I couldn’t believe it had come to this.

At least she still lives with her parents too, I thought.

She still lives with her parents because unlike you, she’s still in her first year at university, another part of me retorted. How did you get into this mess, Ollie?

We sat side by side on the bus. She had evidently accepted the inevitability of ending up back at my house. More than that, she was smiling. Her head, which had been ramrod-straight all night, was tilted towards me. Like so much about her, it seemed quite studied. Which meant…

Oh sweet Mary and Jesus.

It meant that a new problem had materialised. Rose was being friendly with me, but I couldn’t tell how friendly. I wasn’t good at reading situations like this. But after that clusterfuck of a first date, I couldn’t afford to misjudge the situation. If she had made the unfathomable decision that she wanted to hook up with me, then I would look like a moron if I just said, “Okay, here’s the spare room, goodnight.” If she wanted something to happen, well…

For the first time I realised that I wanted something to happen, too.

But, but, but. She probably didn’t want that. I had probably traumatised her. And think how much more traumatised she would be, if I tried to kiss her or something and she didn’t want it, and then she had to spend the rest of the night under my roof… Poor girl.

I was powerless, I realised. Powerless to act, one way or another, until I got a signal from her that was so blatant that even I could interpret it. I just had to wait.

This sense of powerlessness, of being unable to guess what was in Rose’s head, grew stronger as I held her hand to guide her through my dark house, past my parents’ bedroom, up to the spare room. We sat awkwardly on the spare bed, side by side, trying to keep the conversation alive.

Rose was sitting, poised, her hands gracefully on her lap, her back rigidly straight again. Please, I was thinking. Just say “I’m getting quite tired now” or something similarly unmistakeable, and I will find you a toothbrush for the morning and then we can both go to bed.

Rose stared at the bookshelf, casting around for something to say.

“Are those your school yearbooks?”

I closed my eyes and groaned inwardly. “Do you… want to have a look?”

That night, I discovered the most tragic way ever devised for hitting on a girl: showing her the Eton College yearbooks. I hadn’t mentioned where I’d been to school, and this wasn’t the way I would have chosen to bring it up. But here I was, at about 3am, resignedly showing photographs of thirteen-year-old me in an oversized tailcoat. This was a new low, even by the standards of the evening I’d just endured.

Eventually, I ran out of things to say about the yearbooks. I looked up at Rose and grinned weakly.

She was looking at me, with her head cocked slightly to the side. Watching me expectantly, I suddenly realised.

The next thing I knew, we were kissing.

How the hell – how the hell – did this happen?

Rose was pulling me under the covers and wriggling out of layers of clothes. She sensed my hesitation, and paused.

We looked at each other. The area round her mouth was smudged red with lipstick, making her look sweet but ridiculous. I wondered if I looked the same. She smiled. It was a warm smile, but nervous. I realised that she was just as disorientated as me. But however dire the date had been, we had gone through it together.

“Thanks for the evening,” she whispered. “It was baffling, it was bizarre… but it was an adventure.”

“I’ve never had a night like it,” I said.

“Me neither,” she laughed. “Can we do something more normal next time?” And she wrapped her arms around me.


–Read another moderately traumatic adventure: The Full Spa Treatment–

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