That time I went on a Tinder double-date with a "princess."

That time I went on a Tinder double-date with a “princess.”

That time I went on a Tinder double-date with a “princess.”

This article is adapted from my award-winning travel memoir Don’t Come Back. A few names have been changed.


We’d been in our Cape Town Airbnb for all of fifteen minutes when my friend, Nick, walked into the living room shirtless. “I’ve got a Tinder date for tonight.”

I was single for the first time in nearly a decade. I knew nothing about dating apps. Was this how quickly dates were made now? “That was fast.”


“Have you . . . erm . . . exchanged a lot of messages?”

He scratched his neck. “No.”

I lay draped on my front across the enormous plum-coloured living room couch. I pushed down to try to get up but my hands only sank further into its too-soft folds. “Do you know anything about her?”

“Not really, no. She lived in Singapore.” He ruffled his short, lightly greying hair. “I lived in Singapore. So . . .”

“Beautiful romances have been built on less, I suppose.” I supposed, through several layers of intense cushioning.

“There is one thing though.” His eyes narrowed. “She’s twenty-seven. Is that weird?”

This was getting good. I pushed down again, swinging my legs towards the wooden floor. “You need help there?” he asked, as my feet made contact.

“Hell of a couch, that,” I said, once I was finally free of it and upright. “It’s like a Venus flytrap for humans.” I took a few steps towards Nick, who had moved into the kitchen. “So, Nicky, my man, she’s twenty-seven, huh? You’re early forties . . .” I did imaginary calculus in my head as my tongue probed my cheek. “So, yeah, bit weird.”

Our apartment was in the posh district of Green Point, north of the city centre. It belonged to a young female yoga teacher and was full of new-age books, crystals, and hand-written aspirational notes like Remember you’re magic, baby. I helped myself to a glass of water. Nick opened his mouth, closed his mouth, sighed, then opened it again. “There’s something else . . .”

It thrilled me to hear there was something else.

“Her name is Princess.”

I bit down on my lip. “Princess?”

“Yeah . . . Princess.”

“Interesting.” I tried to hide my glee by steadying myself against the countertop, striking what I hoped was a pose of dignified nonchalance. “Can I see her profile?”

He hesitated.

“Not your messages, of course. Just her profile.”

He reached into his pocket, stopped, pulled his hand away, scrunched his mouth, then pulled out his phone and brought up the profile. I looked down at it and air rushed from my lungs as my mouth plummeted like a broken elevator. “Nothing about this profile photo caused any alarms to ring?”

“No.” He squinted. “Why would it?”

I turned the phone screen around. It showed a very attractive woman leaning forward with a come-hither look that would make any man and probably most women, and any animal with knees, weak at them. “Maybe that the only thing she’s wearing is a bra?”

He took the phone off me and scrutinised it. “I mean, you can’t really see anything. The photo ends at the waist.”

“Yeah, but of all the things she wanted to show the world, she chose a photo of herself in her underwear. Then there’s her tagline . . .”

If you can’t handle me, swipe left. He’d shown me the mechanics of Tinder earlier on the trip: swipe left meant you weren’t interested.

“What’s wrong with that?”

“It’s . . .” I probed for the right word. “Brash.”

He blew a raspberry. “I can handle brash.”

I swiped to her second picture. “Christ on a bike!” The first photo had weakened my knees, the second rendered me full jellyfish. In it, Princess had abandoned subtlety altogether; she was topless, with just an index finger resting between glossy lips.

“What?” He asked. I turned the phone round to refresh his memory. Not that it was likely he’d forget this photo in a hurry. Or slowly. Or ever.

“Oh. Very artistic, I thought.”

I bit my tongue, nodded, and handed the phone back. Nick looked down at it as if he knew he’d done something wrong but wasn’t sure what. “So you wouldn’t have swiped right on her?”

“No,” I said. “Probably not. But maybe that’s just me. I’m not so good with, well, women in general, really.”

He turned to the kitchen window and gazed out at the pretty courtyard we shared with a dozen other flats. I wondered if he was thinking what I was thinking. I wondered if I should share with him what I was thinking.

“Nick . . .” I grappled for a suitably diplomatic tone. “Do you think . . . maybe . . . Princess might be an escort?”

He rubbed at his forearm. “Yeah. I was sort of wondering that too. But I don’t know. And then there’s the whole Singapore connection.”

“Hmm. Yeah.” I nodded. “It’s a strong bond, for sure, the Singapore connection. You lived in Singapore. She lived in Singapore.”

“Exactly. I’m sure that’s why she wanted to meet so quickly.”

“No doubt.”

He squinted. “Yet . . .”

I joined the squint. “Hmm . . .”

“There’s also the age gap, the near-naked photos—”

“Artistic,” I corrected.

“Artistic, yeah.” He began looking through me instead of at me. “I feel like maybe I’ve got all the information I need.”

“You’re still going though, right?”

“Do you think I should?”

“Yeaaah. I mean, it’s easily the most interesting thing you can do tonight.”

He gazed up at the ceiling as if the answer might be painted on it. My eyes wandered to a note on the fridge door: Love, Laugh, Lighten.

He snapped me back with a loud hand clap. “Yeah. I’ll go,” he said, before striding off to his bedroom to get changed. I star-jumped back onto the couch, smiling—there was going to be a good story in this, and only Nick would have to suffer the awkwardness required to get it. All was right with the universe. All was soft with the couch.

A few minutes later he appeared wearing a tight, short-sleeved white shirt. “Get up, dickhead. You’re coming.”


“Yeah. Get up. She’s bringing a friend for you.”

I gulped. “Nick, I’m not ready for—”

“Shut up. You’re coming.”





“But I—”

“But I . . .” he said with a whine, and then made air quotes. “It’s easily the most interesting thing you can do tonight.”

He had me there. Or “there” was where I’d trapped us both. Either way, it didn’t seem like I could find a morally defensible way to be somewhere else. He knew this, walked across the room, grabbed me by the arm, ripped me free of the Velcro couch, pushing me out the door.

At a Cuban-themed restaurant on the edge of the Central Business District, we settled into a window seat beside a very large fake palm tree. A waiter in square-rimmed glasses arrived. “Howzit?” he asked, leaving us with two hefty menus.

I looked up from the first of a two-page section devoted to Malibu Cocktails Beginning with the Letter D. “If I were emperor of the world, I’d force all restaurants and bars to limit their menus to just five meals and three signature drinks.”

“If you were emperor of the world, I’d hope you’d have better things to do than that.”

“Look at this,” I said, fanning the pages. “It’s like an encyclopaedia of every cocktail ever mixed.”

The waiter reappeared. “Ready to order?”

“I’ve barely made it through the first dozen pages,” I said. “Can you just pick for me?”

He cocked his head but fired no words.

“What do you recommend?” I asked.

He rolled his top lip towards his nose. “Everything. It’s all good.”

“What’s your favourite cocktail then?” Nick asked.

The man cocked his head more. We were now talking at right angles. “Depends what you like.”

“I like not having to pick from more than five choices.” I pointed at random. “Key West Cooler. That good?”

“That’s good.”

Nick closed his menupedia. “Two of those then, boss.”

I took a moment to admire the room’s spectacularly unsubtle decor: classic car chassis, metal street signs, fake palm trees, and a faded Havana Club logo painted across an entire wall. Countries were complex, but country-themed restaurants? Remarkably simple. Any culture—no matter how old, complex, and multifaceted—could be pulped down to half a dozen trinkets nailed to a wall.

The drinks arrived, and it became clear the waiter had looked us both in the eyes, albeit at a weird angle, and fibbed: the Key West Cooler was not good. Nick took a sip, shuddered, and placed it back on the table as if it might explode.

“Are you excited about the date?” I asked, hoping he hadn’t detected my nerves. I felt as though someone had kicked over a hornets’ nest in the centre of my chest. Another woman being near me and not wanting to get away felt both complicated and vague, like string theory.

He stared out at the street. “I don’t know if that’s the word I’d use.”

“I’m not sure I’ve ever been on a date. Like a proper date.”

“Is that what this is then?”

“I don’t know. For you and Princess, maybe? I’m just your batman.”

He pinched his nose. “Batman? Jesus Christ, Grandpa. It’s wingman.”

A white Uber had pulled up outside. That nest within me got another swift kicking.

The door’s opened and a smell as sweet as our cocktails wafted in on the breeze. At first, it tickled the hairs of our noses, then it gripped them, then yanked them. We coughed and spluttered as the air became perfumed at a scale of malice rather than enticement. Two women got out of that car. The fake flowers on the table wilted. I recognised the woman in the white strappy dress ending just short of her thighs. It would have left little to an imagination had I not already seen what was under it.

Princess. And I was sitting with her prince.

Her friend stood a head taller and wore a silver dress with tassels at its hem. I noticed the definition on her arms. She looked like she could throw a mean javelin. Nick stood up and waved them over. Two kisses on the cheek later, I’d made the acquaintance of Jackie, Princess’s friend. She had a wide, flat face, chiselled features, a strong jaw, and stunning topaz-blue eyes that pinned me back against the wall.

“She only speaks a little English,” Princess said, taking the seat next to Nick. Princess had delicate features, shiny bronze skin, and lustrous black hair tied up in a high ponytail. Her eyes were lined with slashes of silver makeup. She didn’t belong in this Cuban-cocktail museum. She should have been bathing in a waterfall, helping sell shampoo with a voice-over imploring us to “feel the forever.”

Beyond a nice conversation, I had no expectations or desires for the evening. Women were an intoxicating confusion, a pretty one-way street that led only to a dead-end of wooziness, disappointment, and the feeling I was equal parts bad boyfriend, lover, and human. Going forward, I intended to give single ones the wide berth I reserved for rabid dogs, ticking bombs, and on-fire cars. But then there were Jackie’s eyes, like lighthouse beams steering me from the rocks of celibacy.

“You like Cape Town?” I asked.


I’ve always felt that conversations should follow the same basic rules as table tennis: one player serves a topic, and it’s bounced back and forth over a net of discourse. When a rally ends, etiquette dictates that the other person serves. This had been a very short rally. I waited for her to serve. No service was forthcoming.

“Why don’t you like it?”

She squinted, causing the room to darken noticeably. “Don’t know.”

Silence returned, although perhaps it was more accurate to say that it had never really left. Not her native language, I reasoned, and a weird situation—we were the plus ones. So I served a third time. “What do you do here?”

She looked me square in the face, forcing me to raise my oversized, oversugared cocktail as a shield. “Study English.”

Not very hard, I thought.

“And how long have you lived here?”

She leaned back and didn’t answer. The ball had dropped again. I turned to see if Nick was faring better.

“So . . . Singapore?”

“Yeeeeaah.” Princess flashed a smile deep enough to drown in.

“Did you like it there?”

She took her straw deep into the back of her mouth. “Mmmm.”

Nick gripped his glass. “Whereabouts . . . erm . . . I mean . . .” He shifted in his chair. “Did you . . . live?”

She stared up at him as she put the pieces of his question together. “Oh, you know, around.”

“I lived in Marina Bay. Did you live near there?”

Her eyes slid off to the corner of the bar. “Maybe.”

The Singapore connection was becoming more of a Singapore Separation, coincidentally also a cocktail on page eighty-nine of the menu. Nick remained dogged in his pursuit of facts.

“What’s your job then, Princess?”

“Me?” She fluttered her long eyelashes demurely. “No job. I just go where the wind blows me.” She licked her lips.

Nick choked on a mouthful of his drink. “O-kay . . .” He cleared his throat. “And . . . ah . . .” He tugged at the collar of his shirt. I’d never seen him flustered. “Where did the wind . . . err . . . blow you most recently?”


He slapped the table defiantly. “I used to live there too!” First the Singapore connection, now the Amsterdam alliance?! These two really were fated. “Which part did you live in?”

“Oh, you know, around.” Her English was good; her answers were not. Nick’s jaw clenched. I sensed a battle taking place between his brain and his genitals. With each vague answer, his genitals lost a skirmish.

“How long were you there for?”

She let her shoulders sag. “Six months.”

“Uh-huh. And what did you do there?”

She winked. “This and that.”

“What did you do there”—he lowered his voice—“like . . . for money?”

“Money? Oh, money is overrated.” She giggled.

Nick pinched his neck. Despite Princess’s desire not to hit this topic ball, Nick elected to keep it in play. “For example, I’m a statistician. How do you . . . ehm . . . pay the bills?”

Princess reached over and stroked his forearm. “You look way more handsome than your profile picture, Nick.”

He retreated into his seat. Undeterred, she reached up for his bicep. “Do you work out? You look like you work out.” He turned and shot me a wide-eyed, open-mouthed look of terror. Not wanting my enthusiastic voyeurism discovered, I swivelled back to Jackie and pretended I’d not been listening.

I needed a question. Any question. “Where were you born?”

Fine. That would do. We could work with that. She said a word. It sounded like Germon with a hard G.


She repeated the word.

“Game on?”

She shook her head. “Game on!”

“Game on?”

I’d retired from that game. Princess leaned over the table. “Gabon! It’s in Africa.”

“Oh! Gabon! Of course. Gabon. Africa. Sorry.” Princess and Jackie traded sceptical looks. While I couldn’t have contributed meaningfully to its Lonely Planet, I had heard of Gabon. “I’ve been to Africa,” I said, puffing out my chest. Then I remembered I was sitting in it. Blood rushed to my face. Jackie took a loud sip of her cocktail, ending this rally, our longest yet. If I didn’t serve quickly, I was sure the game would be over for good.

“Do you have a favourite English word?”

She blinked. Dawn became dusk became dawn. “Favourite what?”



I suppressed a sigh. “W-O-R-D.” It was game on in Gabon all over again. “Word. Favourite W-O-R-D. Like tree or trifle or tremendous?”

“W-O-R-D,” said Nick, slowly.

Jackie’s head fell back in recognition. “Word!”

It had taken some effort, but we’d summited the mountain of shared understanding. We had a new topic. While it was no Singapore connection, perhaps from this bud of conversation, a flower of discussion could bloom. Jackie considered her answer carefully, probably wanting to do justice to the question and the time it had taken to understand it. She gave a slight nod and put her drink down.

This was it. I was ready. It was time.


No more words came, favourite or otherwise. A small piece of me died—the piece that held hope, I think. I decided to see how long it would take for her to say something if I stopped talking. So, I stopped. She stopped too.

In many ways, she’d never really started.

Princess moved her chair closer to Nick’s. “You’re a very attractive man, Nick.”

He tried to scoot back in his seat but was pinned so tightly to the wall he hit his head. Princess leaned forward, pushing her breasts up in the hammock of her forearms. “There’s no way you’re forty-three.”

“I am,” he said, jumping up from the table and heading towards the toilets. Princess, Jackie, and I sat in a silence broken only by Jackie’s loud slurping. On his return, Nick found Princess had moved her chair so near to his it had become a love seat.

“I’m not really twenty-seven,” she said, as he sat down.


“Yeah.” She breathed on his neck.

“How old are you then?”

“Forty-three, like you.”

Pfft. If you’re forty-one, I’m a hundred and twelve.”

Her hand disappeared under the table, and he leapt up as if he’d spotted a snake. He made a beeline for the nearest waiter while Jackie and I continued our fascinating exploration of how much can be said without words. Even though I’d never been on a date before, I had the feeling this one was going badly. Nick returned, wiped sweat from his temple, approached his seat, paused, took a step backwards, then opened his palms. “Girls, it has been a lovely evening. Really great. Magic. But we’re . . . erm . . . tired, and so we’re going to head off now. I’ve paid the bill and everything and, err, so . . . uhm . . . yeah, was lovely to meet you both.”

With that, like a bullet fired from the gun of awkwardness, he shot off towards the entrance. If looks could kill, the one Princess was giving Nick would land her on death row. She’d clearly budgeted him to be worth a lot more than a plate of chicken wings and two of the worst cocktails humanity had ever poured. I looked at Jackie but found her expression as inscrutable as ever. Its only constant: derision.

I knew I had to get out of the situation, but how? Hug? Handshake? Haiku?

I felt glued to my chair by a mixture of Jackie’s gaze and the sticky sludge of embarrassment. “Err, yeah.” I wriggled in my seat. “Hmm. Terrific.” I slid sideward out of it. “Good talk . . .” I paused. “Ing. Good talking. Err. Yes. Been great.” I stood up and leaned in to hug Jackie. She sensed it was coming and leaned back, leaving me no option but to pretend I’d merely been stretching. I straightened, rubbing the small of my back, as if I’d finally dislodged an annoying kink, then smiled at them both with my mouth but not my eyes. “Have a great evening,” I said, breezily. Then I waved.

I waved.

Why did I wave? What was I thinking? Was I thinking? How does one think? How could one think better?

On the interminable walk back outside, I decided that if they made idiots bigger than me, I’d never met one. I found Nick leaning against a lamppost, bent over as if winded, that vein throbbing in his neck—his stress tell.

“You alright?” I asked.

“I need a minute.”

“Gabon, I mean, come on, Nick. It wasn’t that bad.” By the end of bad I was laughing so hard I had to lean on his shoulder for support. He kept his eyes on the pavement. “I’m not there yet.”

I was the mayor of there and soon was wiping away tears, which irritated Nick so much that he grabbed my arm and pulled me up the hill towards home. His steps were fast and heavy. “That was an ambush.”

“Dude, you had all the information.”

He grimaced. “I had all the information.”

“I guess she proved a little too brash even for you, huh, Singapore Sam?”

He stopped, our eyes met, and his tetchy facade collapsed. We tumbled shoulder to shoulder, laughing, into a Belgian beer bar. “Did you ever work out if she was an escort?” I asked, as we took seats at the bar.

“No. I mean, she must have been, right?”

I gave a small nod.

“I have no problem with that. I’m sure she’s got her reasons. I just don’t know why she wasn’t honest about it. What about Jackie?”

“I don’t think so. Unless her specialism is seduction by indifference.”

“Yeah, very much the strong, silent type.”

“I don’t know,” I said. “I think we were starting to click.”

We laughed so much our waiter came over to ask if we were okay.

“Do you regret doing that?” I asked.

Nick’s shoulders slumped. “Yes. Completely. One hundred percent. It was awful.” A young couple passed, holding hands. He took a gulp of his beer. “Ask me again tomorrow . . .”

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