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

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.