After a long-term, online, long-distance relationship with a guy that turned out to be transgender, THE UNDATEABLE GAY goes to meet the man of his dreams…
I’ve deleted all my dating apps. There’s not one to be found on my iPhone. I was fed up with all the curious straight men chatting to me on Plenty of Fish. And annoyed at everybody on Grindr being shallow and only wanting one thing. And don’t even get me started on Tinder. I may only be in my 30s but I’m rather Granny like when it comes to technology.
After an unfortunate incident involving a 70-year-old lady and swiping right, and then being slightly stalked and receiving numerous invites for coffee and cake, I decided that Tinder was no good for me either.
I’ve taken to more intellectual apps these days. My favourite is Words with Friends. For those of you not in the know, this is Scrabble. But on your phone. And you can play with anyone, anywhere in the world.
One day, I started playing with this very handsome man called Joshua. Yes, you get to see a photo of who you’re playing with. I kept perving on his picture whilst waiting for him to play his move, praying he would start a conversation.
And then the Lord answered my prayers and a chat popped up. Although it was a little ambiguous. Remember, this is not a gay app, so there’s no way of knowing whether the person you’re playing with fancies you. Or even if they’re a raving homo.
After putting my journalistic training into practice, it was soon confirmed that Joshua was flirting with me and did indeed fancy me.
He was only 25. Ten years younger than me but I decided that I could be a cougar if I wanted. And he lived in Southampton. I was a bit disappointed that he wasn’t in London but hey-ho, it’s only an hour’s drive or a train ride! And besides, I’ve become so institutionalized with being single, I thought it’d be perfect to have a man who didn’t live in my pocket.
We spent months talking on the phone, exchanging WhatsApp messages and sending each other photos. I don’t think I’ve ever fancied a man as much as I had Joshua.
He was just my type; Tattoos, quite butch and BLOODY handsome.
We had so much in common. We drank like fishes. We had potty mouths and both adored the C U Next Tuesday word. And we both had quite common, rough around the edges accents. Surely it was a match made in heaven.
We even discussed growing older together. And I’d never met another man who shared the same views as me about how we should behave in a care home as an old couple together. We both agreed that it would be wheelchair races through the corridors. And slipping under the table for a sly blowjob during bingo.
A few months of a long-distance telephone relationship, I decided it was finally time to bite the bullet. Being the older gentleman, I took the lead and arranged to get the train from London to Southampton. I was finally going to meet the man of my dreams, my perfect match.
Two days before the big first date, he sent me a message declaring, “We’re perfect for each other, I swear.” I swooned at the words and I was of the same opinion. We were so similar, the way we spoke, the thoughts we had. It was scary.
The night before I was due to catch my train to Southampton, we had a very interesting text conversation.
JOSHUA: Probably something I should tell you before you come in case it puts you off.
JOSHUA: I’m transgender. I was born a female. I know you’ll probably freak and it’s fine.
MARK: I don’t give a shit. I know you as Joshua and I fancy you.
The morning of the date arrived and the sun was shining so brightly. The sun shines on the righteous, my dear Nan always said.
I arrived at Southampton Docks in plenty of time for our meeting. We’d agreed on 1 pm. It got to ten past and no sign of him. I tried to call. No answer. It got to twenty past. I sent two messages. No reply.
As the clock hit 2 pm, I thought, What a C U Next Tuesday. I’ve come all the way from London and you don’t even have the common human decency to show up or even respond to my attempts at contact.
Being ever the positive boy that I am, I decided that I would not waste my day. The sun was beating down and it was the most beautiful day so I spent my unexpected free time wondering around Southampton. I had a few glasses of wine, ate a spot of lunch and watched the world go by.
A few glasses of savvy b later, I decided it was time to get the train back to London. But not before I sent one final message to Joshua. I simply had to have the final word:
“I had a lovely day in the sun at Southampton Docks. I thought it best not to waste the train tickets so I spent the day in Southampton anyway. I wouldn’t worry what people think of you because you’re transgender. I’d be more concerned with what people think of you because you’re a bit of a cunt.”
Mark David Woollard graduated from Brunel University, West London in 2009 with a Bachelor of Arts degree in Creative Writing and Journalism. Since then, he has written for many publications as a freelance writer. He has been ‘The Undateable Gay’ for The Gay UK magazine since 2015 where he documents his unsuccessful dating life. He wrote an opinion column for the national Student Times, discussing LGBT issues.
He also writes educational pieces for ‘Massage World’ magazine, giving advice to Reflexologists about treating certain ailments. He authored a novella in 2013 entitled ‘The Fun and Frolics of FIFI a L’Orange’, the crazy adventures of a drag queen.
And is currently working on a series of LGBT books for children and a collection of flash fiction.
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