The transvestite, the fat cyclist and the woman from Chest Monthly: writers' tales of weird dates

Stories of the path of romance from A.L. Kennedy, Jack Whitehall, Celia Walden, Toby Young and many others

13 December 2014

9:00 AM

13 December 2014

9:00 AM

Toby Young

Status anxiety columnist

About 15 years ago, when I was single and living in New York, I acquired what I can only describe as a stalker. A woman took exception to a newspaper article I’d written and started bombarding me with emails. For about a year, she sent me three or four emails a day, demanding a reply. In one of these emails she claimed to be a columnist for a magazine called Chest Monthly, and that piqued my interest. So I invited her on a date. We agreed to meet in a café and she was quite difficult to spot because, contrary to my fevered imaginings, she was completely flat-chested. I asked her how she’d managed to land a job as a columnist for Chest Monthly. There was a deathly silence as it dawned on her that this was the only reason I’d asked her out. ‘Chess Monthly,’ she said, coldly. ‘Not Chest Monthly. Chess Monthly.’ She stopped emailing me after that.

James Runcie

Author of The Grantchester Mysteries

I met Lucy at a dinner party in the early 1980s. By the main course we were holding hands under the table. She told me she was about to go travelling in China. By the time we reached the pudding I told her that I would wait, and after a bit of late-night kissing (in which I was told that I tasted of ‘erotic raspberries’) she went home.

She phoned before she left. ‘When we sleep together it will be like a wedding night,’ she said. Then she added that her stepfather wanted to meet me. Even I thought this was a bit speedy, but I went to see him all the same. We talked about politics, the miners’ strike and the Cold War. The miners would be all right, he thought, since they all had video recorders and could spend their enforced leisure time watching films.

When Lucy returned in December I had everything ready: flowers, dinner, champagne. She looked surprised but got into my bed wearing her pyjamas. ‘Here we go,’ I thought.

‘What are you doing?’ she asked after a tentative approach. ‘I wasn’t expecting any nonsense.’

This was dispiriting. ‘What do you think I’m doing? You told me I tasted of erotic raspberries. You said…’

‘Oh I didn’t mean any of that. I thought you needed cheering up. Besides. There’s Richard…’

She turned onto her side.

I looked out of the window into the dark night. It wasn’t snowing or anything appropriately seasonal. It was just going to be one of those shit days where it never gets light.

‘I hope you have a nice Christmas,’ she said. Then she began to snore.

A.L. Kennedy


I dislike dates. It’s either a yes, or a no. Why date? Sadly, I am both bad at reading the signals which indicate the outbreak of a date and attractive to people who are bad at signals. This means that I end up — often in coffee shops — with a variety of men who suddenly exhibit enthusiasms I cannot return. Among these gentlemen would be the portly chap in Day-Glo cycle shorts, the man who brought an ugly plant with him, the man who cried, the man who talked unendingly about the rows he used to have with his last girlfriend, the man who sat next to me, miserably unable to speak at all, and the man who got crawling-drunk and then confessed something, mumbly, before hiding in his hotel room for a day. And then there was the man who gave a brief — but not brief enough — summary of the actions involved in coitus before suggesting we try it. I can only repeat: we weren’t on a date. It was just coffee. I was honoured by your attentions, but did not require them. When I do require attentions, I say so. Really. Thank you, but no.

Dan Snow

Historian and television presenter

I was in the American Colony Hotel in East Jerusalem. We were dining in the courtyard of this former residence of a pasha and his numerous wives, under the tall mulberry trees, when she walked in. Let’s just say that among the overweight male clientele she stood out like a gleaming Israeli settlement in a sleepy Palestinian farming valley. With all the chutzpah of an Israeli army strike across the Suez Canal I asked her out for a drink. She replied in the unmistakable accent of the American Deep South. I met her later as arranged and threw my entire being into the tour of Old Jerusalem. I liberally scattered the six words of Arabic I knew, bought food from street vendors, ruffled children’s hair, dredged the darkest canyons of the mind for any historical context for the buildings we passed, and made it up when the memory failed. I distinctly remember thinking that this was life of which the 15-year-old Dan had dreamt. The conversation flew. She studied history and, joy of joys, she was the daughter of the US Marine Corps’ foremost expert on counter-insurgency. But then came the depleted uranium round through the armour plating. She was here on a pilgrimage. My blood ran cold. Like the Arab armies in 1973, early optimism was replaced by the certainty of defeat, even humiliation. I walked her back to her hotel in West Jerusalem. She was sharing a twin. With her grandpa. After decades of studying military history, I know defeat when I see it.


High life columnist

It was around 1972, my father had just had his portrait painted by Salvador Dalí, an old buddy of his, and Dad and I went to the Meurice hotel in Paris where Dalí and his wife Gala unveiled it. We had champagne, Dalí and Dad cracked jokes at my expense, and then the great man asked me what I was doing with my life. I told him I was off to London to try and crack the English scene, journalist-wise, that is. ‘Eh bien, il faut que tu appel la plus jolie de tous, ma cheri…’ He gave me her telephone number and said he would ring her. Two days later, in London, I called the lady and, yes, she was free for dinner. We met at Annabel’s, where Louis, the maitre d’, gave me a hell of a table. She was blonde and beautiful. Her voice was low and she was taller than me, but what the hell. After dinner I took her to my flat in Dunraven Street nearby. Holding her hand in the cab, I noticed it to be twice the size of mine. After some more drinks at home I pounced, but just as I did, I noticed her larynx was — well — as big as a Tiger Panzer. So I fished into my wallet, pulled out a rather large bill, and asked for the truth. Was she… a man? ‘Yes, sweetie pie, I am a hell of a man and all yours,’ she or he said. I gave her a brief peck on the cheek and showed her out. That Dalí, what a card!

Tanya Gold

Food columnist

My worst date was with the man who is now my husband. It was in February 1994, and we were both freshers at Oxford. He took me to see Schindler’s List. Schindler’s List is not really a date movie, even if its score does feature on The Most Relaxing Classical Album in the World… Ever! (Volume 2. I love the ‘Ever!’) It’s the genocide of European Jewry, I suppose; it just doesn’t make me want to mate with someone so tall, blond and blue-eyed they could conceivably be a Lebensborn baby. I realise now that he had a strategy; he thought I might be so upset about the Holocaust — as if it was news to me! — that I would have sex with him and produce a half-Lebensborn baby.  The strategy failed for 19 years and nine months. He also bought popcorn. Schindler’s List is not really a popcorn movie, either.

Jeremy Clarke

Low life columnist

I had been catastrophically and unceremoniously chucked by a woman with whom I was insanely in love. My love for her had been like a psychotic illness, and when she ended it, I sat at the kitchen table for two days, immobile with grief, listening to Moby singing ‘Why Does My Heart Feel So Bad?’ on repeat. Then her mum came round to the house to give me a stiff talking-to and a haircut. ‘It’s no good sitting there moping,’ she said, snipping at my head. There are plenty more fish in the sea. I wasn’t so bad-looking. Tell you what, she said. She had a friend: 40, plenty of money, vineyard. Why didn’t she fix us up with a date? I must wear my nice green shirt and try to be confident. Confidence, she said, is three quarters of attractiveness. So the next day, wearing my nice green shirt, I pushed open the door of this trendy café and looked around for a woman wearing blue glasses. There she was, at a table, deep in conversation with this bloke in a green shirt whom she’d obviously just met and mistaken for me. They clearly fancied the pants off each other. Lacking even a shred of confidence, I turned around and returned to my kitchen table, to Moby, and to my bottomless grief.

Jack Whitehall


My worst date happened when I was fresh out of university. I took her to a very upmarket restaurant for our first date. She was an older sophisticated lady and I wanted to pull out all the stops. The wine flowed, as did the conversation, and things were looking good until the bill came. We’d run up a hefty tab, but I’d already settled it with myself that she was worth being skint for the next month for. I slammed down my Nationwide debit card and smiled at her. Moments later, to my horror, the waiter uttered the words no man wants to hear on a first date: ‘Sir, your card has been declined.’ I hit panic stations, and after forcing him reluctantly to check it several times, was left with only one final play to save face. Call my mother. What ensued was a humiliating spectacle in which I argued with my mum on the phone in front of the poor girl until out of embarrassment she decided to just pay the enormous bill herself. There was no second date. Now I always bring cash.
Jack Whitehall’s latest DVD, Jack Whitehall Gets Around, is out now.

Matthew Parris

Spectator and Times columnist

One evening in 1995 some friends brought a friend to dinner at my flat. His name was Julian, and he seemed rather bright.

As it happened, the Nigerian ecological campaigner and fighter for rights of the Ogoni people, Ken Saro-Wiwa, was in prison having been convicted on trumped-up charges of incitement to murder. His case had become an international cause célèbre. His conviction carried the death penalty; and he was widely believed to face death by hanging. I was in full ‘old African hand’ mode, and announced to the table that I knew the ‘African mindset’ too well to believe Saro-Wiwa would actually be executed, now that the eyes of the world were on Nigeria.

In a matter-of-fact manner, my guest, Julian, replied: ‘Actually he was hanged earlier this afternoon.’ He did so without hesitation or apology. I was deeply impressed by his cool, and decided I wanted someone like Julian to work for me as a researcher and adviser. We became better and better friends. Gradually we realised we had better get a civil partnership.

And that’s how it was. Not exactly a date — but then I’ve never really been on a date. Gradual is often best.

Celia Walden

Journalist and novelist

It was supposed to be an interview, not a date. But Piers seemed to have other ideas. The Ivy dinner crowd was particularly amusing that day: Baroness Thatcher to our left, Louis Walsh with a group of X Factor ingénues to our right. In the corner, Salman Rushdie was seducing some improbably beautiful girl. Piers spent most of our lunch foghorning out greetings and taunts across the restaurant. I remember thinking that I’d never met anyone quite so loud. Over sticky toffee pudding Piers casually informed me that I was the chosen one. When I dropped him an email the following morning to thank him for lunch, I felt it only fair to add as a postscript: ‘So that you know, it’s never, ever going to happen.’ ‘Oh it will,’ he wrote back. Five years later, he read out the exchange on our wedding day.

Melissa Kite

Real life columnist

My dates are always a disaster, hence the fact I’m still single. I remember a particularly fraught early romantic foray when a conscientious young fellow took me to a modern art gallery and a two-character David Mamet play in one afternoon.

I made it through the conceptual art exhibition, but halfway through the first act of Oleanna, I confess I told him I needed the loo, crept out, got drunk in the bar, then ran away.

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For more details of these and other similarly humiliating dating disasters, Melissa’s forthcoming book, The Art Of Not Having It All is available to pre-order on Amazon.

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Show comments
  • The literary editor who declined my first M.S did however set me up with a date. The lady was a Deleuze scholar but was struck dumb my apercus ( e.g. ‘apres moi le Deleuze’) I suddenly became aware that I had a chance to pull. I went to the gents, wetted my hair and took off my (very thick glasses). When I returned the lady, who had undone her hair (an erotic signal in my native South India), showed every sign of impatience to leave with me. It was only once we got onto the street that she mentioned that she needed a black pimp, having just arrived from Amsterdam. I put on my glasses. It wasn’t the same girl. The other had escaped while I was in the Gents.
    Still counts as my date ever.

    • A Deleuze scholar? Do you realise how oxymoronic that sounds?

      • What can I say? It was the early Nineties. Sokal hadn’t been invented yet. And I didn’t need Viagra. Not that I take Viagra. I mean I start off intending to take Viagra but, coz my bifocals aren’t from Specsavers, end up taking the roofie- so a good time is had by all.

        • An excellently calibrated response. Sokal and Bricmont are two of my heroes. Also, a most amusing riff on Viagra and roofies!