Strange men: gay dating through the looking glass

The playwright

I’m sitting in a cafe in a converted art deco cinema in Chester feeling hopeless about my future when a German guy messages me on Grindr out of the blue. He’s staying in a holiday home on the Welsh coast with a group of German and English friends. We swap messages intermittently for two days and his German is beautiful and poetic, the kind of language you just don’t encounter anymore in casual conversation - educated and flowery yet not affectatious. He seems disconcertingly into me given how briefly we’ve chatted, so I try to temper his expectations. He tells me he’s flying back to Frankfurt at the end of the week and would love to meet me before then, so I pick a country park in Wales that’s about halfway between us and we agree to meet there the next morning.

I get there early and hike round the park for an hour or so, to scout it out and so that the day isn’t entirely wasted if he stands me up. Given his fervour for me, I’m expecting him to be some kind of weirdo or lunatic. But nope, here he is heading down the path towards me - a great big hunky blond German playwright, if anything more attractive than his pictures. He’s driven two hours to get here. We disappear into the depths of the park, and I kiss him by the bank of a dried-up river. We snog some more on a country lane, then picnic on a high meadow overlooking the Clwydian hills. We talk and joke. About German politics, Welsh grammar, his life, my life. He tells me about the theatre he runs together with a female colleague. About working in Moscow in the late 90s, and the nascent gay scene there - “das waren die goldenen Zeiten”. He’s kind and keeps giving me water from his flask.

At the end of the day, he says he’s had a lovely time, and that he’d like to meet again. When I set off to drive back, he even stands and waits at the exit to the car park to wave me off. We chat a little more that evening and the next day. Then he deletes his profile.

The singer

I drive to an isolated village an hour and a half from Manchester to visit a professional singer I’ve been chatting to for a year, mainly just as friends but with occasional flirting. We’ve telephoned in the past, so I have a reasonable sense of him as a person. My impression is of a wholesome, intelligent and sensitive man who beneath the surface is profoundly lonely and who has thrown himself into volunteering and charity work to keep himself busy. This is something like our sixth attempt to meet, as his packed and ever-changing calendar has made it hard to agree a date.

I arrive and we talk for six hours. He’s animated and effervescent in a way that’s almost hard to take, and everyone we encounter in the village seems to know him, as he’s a lay preacher and parish council member. His house is chaotic with items littered all over the floor and Christian paraphernalia adorning the walls, from simple crucifixes on chains to ornate Orthodox icons that he commissioned from a wood-carver in Romania. There’s a St Stephen watching over the downstairs loo.

In his church, he shows me the pipe organ, and I tell him the tale of my organ teacher in the 1990s who turned out to have been sexually abusing one of the other students. He tells me about being sexually abused by his singing teacher between the ages of 13 and 15. Compared to others I know who have experienced similar, he’s surprisingly at peace discussing it and seems to have processed it well, even explaining how it informed his approach to child safeguarding in the local church community.

We return to the house and talk some more in the garden, where he divulges his history of cocaine abuse. His elderly neighbours are close by in the adjoining garden - one picking damsons, the other mowing the lawn - as he chatters away about poppers and anal bleaching. He says that during the years he lived in London, he slept with over 1000 men and logged them all in a spreadsheet with notes and marks out of ten. He stopped abruptly eight years ago after moving to the countryside to get away from it all and has barely had sex since. A large pheasant appears on the garden wall, and he dashes to fetch handfuls of seed to feed it with. As it pecks away loudly at the food, he tells me I’m the only guy from a dating app who’s made the effort to come and see him in eight years. The pheasant is called Dave and has been coming to see him for the same amount of time. There is no exchange of seed.

Because he’s so relentlessly upbeat and chatty, he gives the impression of not listening, but this is mistaken - several times he refers to things I said earlier in the day, and I can tell that he has listened deeply to everything I’ve told him. He talks about his own death in a way that’s unexpected and matter of fact, but says that even at his lowest, he has never contemplated suicide. He tells me about arguing with the Archbishop of Canterbury at a church function, and seeing Graham Norton get carried out of a drugs party after shitting himself. The next morning I feel poleaxed by grief.

The cowboy

On the outskirts of Manchester, I go to meet a deceptively kind graphic designer who lives in a one-bedroom apartment in a converted mill. He has a fetish for cowboy boots and owns 18 pairs. Compared to most kinks this seems disarmingly innocuous and old-fashioned, so I agree to try a pair on. The apartment is decorated in a Halloween theme and is also home to a discreet Christmas tree that he tells me he keeps up year-round; when Christmas comes for real he gets out a second, larger one. The only non-Halloween, non-Christmas decorations are dozens of Marvel figurines and three large Drag Race posters.

He is perfectly nice and does nothing wrong all day, but something about him repels me, I think it’s because he’s a little too submissive, a little too giving, in a way that makes me uncomfortable. He says a number of things that mirror or anticipate my own thoughts and feelings, and I feel like I should like him more. He tells me he’s just left a four-and-a-half-year relationship with a guy who didn’t like to be touched, who wouldn’t even cuddle with him on the sofa while watching TV.

We make love, observed by the novelty skulls and large Krampus mask that festoon his bedroom shelves. Before I leave he asks if he can take a photo of me wearing the boots, and I say no. He tells me that the government is secretly cloning humans.

The barrister

I see him for the first time in four months, and on first sight it strikes me as bizarre and abstract that we were ever together (and that even after we broke up, our sexual relationship continued for over a year), as if the whole thing were a mirage or something that happened in another life. He’s dating a 28-year-old and his ex-wife has blocked him on WhatsApp.

When we go to the counter to order, he leaves his laptop bag completely unguarded by the cafe door, so I pick it up to stop it from being stolen. He’s just come back from the Wagner festival in Bayreuth, which he attended with a divorced straight friend he’s known since they were at Oxford University together 38 years ago. Two days into the trip, his friend came out as a trans lesbian called “Emma”, and proceeded to wear “a series of increasingly flamboyant frocks” over each night of the festival.

We have an argument about the fact he constantly forwards me memes and jokes but never has a proper conversation with me anymore. He says I never message him first, which is untrue. We both agree that electronic communication is part of the problem. He says his teenage son calls him “the world’s worst dad” and “a fucking moron” and refuses to meet his boyfriend. I tell him I haven’t been happy recently and I need people to be a bit more pastoral towards me. I tell him about the German guy and that things like that affect my ability to have a secure attachment to people.

He shows me a picture of his new boyfriend and tells me how wise and grounded he is, and that he helps him deal with his ex-wife. I wonder why a 28-year-old has been roped into mediating between warring forty- and fiftysomethings. I wonder how his cat is but don’t ask. He tells me that his boyfriend took his passport off him when they went on holiday to Italy for a week and only gave it back to him on the last day. I wonder why he has introduced a 28-year-old he has been dating for two months to his family. We talk about the Queen. I wonder why he allows everyone else to take charge of his life - his ex-wife, his son, his boyfriend, me for a while - and why he’s somehow never accountable himself. He tells me his boyfriend’s family like to go to Dubai together every year to be “pampered”.

After we part ways and he returns to his office to work, I walk through a large redevelopment area just outside Manchester city centre. There is graffiti in French. The disused canal docks have been converted into a marina, surrounded by avant-garde housing that could be in Amsterdam-Noord or Islands Brygge in Copenhagen. A sign says something about “urban splash”. I stand and look across the water at the vast edifice of a cotton mill converted into high-end rental apartments; only the facade remains.