I wasn’t actively looking for a man, let alone a man in his 20s, not another one, not after the one I wrote about in my last column. But it happened while I was reading that column aloud on stage at an event in Soho, hoping to entertain people with the story of being a 48-year-old woman who tried to date a 22-year-old man while my 13-year-old daughter was on a sleepover. It hadn’t occurred to me that this would function as some kind of dog whistle to other young men in the audience.

When I came off stage, I bumped straight into a male friend of mine who was with a male friend of his, and our chat quickly turned to the horror of the dating apps, the horror of ourselves, how we ruin everything. At least, that’s what my male friend and I were saying. The male friend of his, though, said he’d only had positive experiences on the apps, thought people were nice on there. Weirdo, I thought, ignoring him. ‘Your reading was absolutely wonderful,’ he said. I was wearing a cap that said BIG MAN, despite being a woman of average height, and he, a tall man, was wearing a cap that said nothing, and we were in a basement and it was dark, but he was – maybe 34? And that would be alright?

‘I thought you were divine,’ he added, looking into my eyes with an intensity that can only be described as homosexual. No straight man has ever described a woman as divine. Still, I had to be sure, so I came up with a genius way to subtly check his sexuality: I asked him what his demographic was on the apps.

‘What?’ he replied.

‘I don’t mind about age?’ he added, looking hopeful.

‘I meant men or women,’ I said.

‘Oh! Women!’ He said.

‘Oh!’ I said.

There was a pause.

‘You have lovely skin,’ he said.

At this point, our mutual friend walked really quite far away from us, unable to continue listening to two people trying to flirt in the same way that two people might try to speak Japanese, if they had never heard anyone speak Japanese before.

In my last column, I’d explained that I’d wanted the 22-year-old to buy me Champagne but he’d turned up with some cheap piss from the corner shop. So when this new guy arrived, he surprised me with a bottle of crémant. It’s classier than Champagne! It’s giving connoisseur, not oligarch! ‘I was paying attention,’ he said, when I burst out happy laughing at the sight of it. And the lovely taste of it. He was more well-spoken than I’d remembered, and the thought suddenly flashed through my mind that my beloved grandmother would have really liked this man.

So I asked him how old he was, just to check. He told me he was 27.

Fuck’s sake. Not again.

Still!

At the end of the night, when I was wearing little more than a sheet, having politely told him he couldn’t stay over, he put on his coat and said, equally politely,

‘So when did you have herpes?’

‘What,’ I said.

‘It’s totally fine, it’s honestly not about judgement,’ he said, ‘I’d just feel comfortable knowing the timeline.’

The word timeline sounded as funny to me as the word demographic had sounded to him. I wasn’t sure where this joke had come from but he was keeping a straight face really well – all kudos to the guy.

‘To the best of my knowledge, I have never had herpes or any other sexually transmitted disease,’ I said, but he looked really serious and insisted I had said otherwise.

I mean – what? Why would I have made that joke? And it was definitely a joke, but – oh god, what I did remember was the day before, going to the shop for something my teenager needed, texting her saying ‘I’ve got it’ and then adding ‘herpes’ so, clearly, the part of my brain that made inappropriate venereal gags had been active and seen online in the last 24 hours. And quite a lot of that crémant had been drunk, by me, and – is there a word for inverse catfishing? Turning up in a man’s life looking perfectly attractive then doing everything in your power to make him think you’re ugly? I’m starting to think I might be a fishcat.

A few weeks later I went to a party full of writers, men older and more established than my recent encounters, the sort of men I should probably fancy. It was a sultry evening and as I sat on the Overground watching half of north-west London go by, a fox trotted past the railway line, a plastic bag in its mouth like it was delivering a takeaway. The sky darkened but it was still hot, and the heat and the dark collided to make me feel like I could do anything, like I could ride on the back of that fox, invincible. I felt so invincible that I almost started to understand why one in eight British men believe they could win a match point off Serena Williams, and why an even higher proportion reckon they could land a plane if something happened to the pilot. 

This party was full of literary men, though, and their secret self-belief is that if they’d wanted to write a book like Sally Rooney, the most acclaimed novelist of their generation, they could have done. I arrived late and the place was already packed with such chaps, whole podcasts of them everywhere I looked. Most of them married, but it didn’t stop them flirting and it didn’t stop me flirting back. Their wives appreciate it if you do this – it’s like you’ve offered to take their dog for a walk.

I got introduced to someone called Ed and said how nice it was to meet him. He said that’s what I’d said when I was last introduced to him, 45 minutes previously. Then he asked if I didn’t remember him coming to one of my own birthday parties, years before. This wasn’t even a fair fight, given that every single man in the room was called Ed. I wondered if there was some kind of conversion course I could go on. Just to reset my sexuality to fancying Eds.

The next day I told the 27-year-old I needed to see him again. He took me out for dinner and we ordered oysters and both coyly pretended not to know how to eat them, even though you just eat them. Inspired by the shape of our dinner, I asked him if I’d really told him I had herpes. ‘Not only that,’ he said, grinning broadly, ‘but you also sat me on your sofa and said, “Why are you here? Do you have mummy issues?”’

‘I did not,’ I said.

‘Oh you did,’ he said.

‘Well, do you?’ I asked

‘No,’ he said.

‘Have you had girlfriends who were older than you?’ I asked.

‘All of my girlfriends have been older than me,’ he said.

In bed the next morning (my child really does go on a lot of sleepovers) he said I had ‘Big Dick Energy.’ I told him that was the most romantic thing anyone had ever said to me. Alright, so I had also told my last long-term boyfriend, the Greek, the same thing, but that was when he’d said that he’d never met anyone who enjoyed being them as much as I enjoyed being me. And when I’d told the Greek that that was the most romantic thing anyone had ever said to me, he’d replied that he hadn’t necessarily meant it as a compliment. We were lying down and it was cosy so I rested my head on the 27-year-old’s shoulder. But then that felt too subservient, too effeminate, so I moved it off again.

‘Oh come on,’ he said kindly, ‘You can still have a big dick and rest your head on my shoulder, don’t limit yourself.’

It took all the strength I had inside me not to say that the only thing threatening my big dick was actually my herpes, but that was the sort of joke I had made back when I was a mummy. Now I was a big man. Now I was the daddy. I could beat Serena Williams. I could even beat Novak Djokovic. I would soon be landing my plane at Wimbledon.