Casual sex is fun – but when is it time for a relationship?

A Single Man: after a best friend bags a boyfriend, the appeal of the one-night stand comes into question in this week’s gay sex column.

Most of my friends are in relationships, either by choice (I hope) or because they don’t really know how to be single. I’ve never been in one, so over many years I have developed a fool-proof knack for riding solo: enjoy your own company and have enough single mates knocking around ready to get off their heads. Of course, it helps to embrace one-night stands, too.

On Saturday night, my mates, The Group, met in a new-ish bar in Peckham. I was slightly hungover, having gone out the night before, dropped a pill and had a quickie in a cubicle with an older guy. My head felt a bit fuzzy, but The Group had been summoned for something especially important.

I arrived around an hour late and the bar was packed. Sitting in the middle of the table was Single Mate, though Single Mate was no longer Single” Mate – her new boyfriend, the reason for us lot meeting tonight, was next to her. We’ve been best friends for six years and she’s only ever had very minor brushes with boys, all of whom were total wankers. But this time, she’s met someone who suits her, looks good next to her and treats her really well. If there’s anyone who deserves to find love, it’s Single Mate.

She’d felt a little nervous in the days leading up to introducing him to The Group. But he slotted in so well, making jokes and chatting to everyone. After we all got suitably pissed down the local, I got home, sparked a fag, poured a tequila and started thinking: is that what I want, too? To meet someone who loves me, eventually proposes and we end up having a proper wedding and everything?

I’d never been duped by a shag before, and I felt like a right idiot”

There’s a part of me that totally wants that. But there’s also the Single Man who wants to abuse the gay privilege of not being deemed a societal freak if they’re still shagging around at the age of 40. Because parts of society think we’re societal freaks, anyway.

I thought about it a little bit more, then… fuck it. I opened Grindr. G popped up: a 46-year-old Italian from Naples, whose picture was him sawing some wood, wearing a tight Adidas T‑shirt. He looked decent enough and seemed like a laugh when we chatted for 10 or so minutes. Plus – big plus – he only lived down the road.

I threw on some fresh clothes, sprayed a bit of Tom Ford Extreme, swilled my mouth with Listerine and was on my way. It took a few minutes to find G’s flat but he messaged me, saying he was standing on a balcony waving. I looked up and there he was, waving in the dark distance, an EU flag hanging over the balcony, covering his legs.

Four flights up, I knocked and, as the door swung open, froze. He looked like his pictures on Grindr, but about 30 years older. I surveyed him up and down, raised an eyebrow at the skinny jeans, appraised the hunchback that was non-existent in the photos and narrowly dodged a kiss. I’d never been duped by a shag before and I felt like a right idiot.

Then, while I thought about the quickest possible escape route, G asked: Do you mind ket?”

I don’t do ket, thanks,” I replied, truthfully.

No, do you mind cat?” G said.

He pointed to the corner of the living room where, lo and behold, there was a really pissed off-looking cat. Maybe it had been catfished, too. I turned back to G and explained that I wasn’t into it. Luckily, he was understanding. I reckon he knew he was bullshitting all along.

I made my way home, still feeling a little horny, so I messaged a Swiss guy, J, who I’d been speaking to the weekend before. Within 20 minutes, I was getting fucked in his bedroom. It was nice being with J. He was undeniably good in bed and we were both a little tipsy, which can make for fun, clumsy sex.

After we’d shagged and we were lying in bed talking about our jobs, Monday mornings and what we thought about the new-ish deli round the corner, he told me he was married. That’s not usually a problem for me, especially after he explained that he’s in an open marriage (his husband was away for work – a classic). But when I woke up the next morning, to him giving me head, I felt a little restless.

I couldn’t shake the feeling that perhaps I’d been too reckless the night before. That I was desperately chasing a fuck to fill a void where… what? Happiness and contentment should be? That, unlike all those people in relationships, I needed validation from a random bloke every other night, staggering home with a latte and a sore bum, about to spend Sunday with only the hangover from hell for company – again. I wondered if G and his cat ever felt the same. I wondered what Single Mate and her boyfriend were doing. I wondered if it was time for a date.

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