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.