The Accidental Columnist: The good, the bad and the ugly of my dating history

Columnist Dean O’Reilly has enjoyed the ups and downs of dating and so he’s sharing three dates he’ll never forget because of what they taught him.

Connections

Dating can be hard for anyone. I’ve spoken about the challenges of dating when you don’t know yourself. And when you add being gay, sober and all other facets of my personality into the mix, it’s been complicated for me.

But one thing my dating history has always been is memorable, and these three dates stick in my mind for what they taught me.

These are all real stories with minor changes for privacy. Believe me, I couldn’t make them up if I tried!

Flights of fancy

I had been speaking with a guy on Instagram for the guts of a year. Not every day, but enough for us to want to meet. He lived abroad so the plan was for him to fly out and see me. I was excited because I’d never had a guy go out of his way for me like this. He bought the flights and he would stay with me after his first night.

Excited, I met him for brunch on his second day. When we met, he said he’d been out the night before and still hadn’t slept. It was 2pm.

After an hour of small talk, he came back to my house. He stayed for half an hour before proclaiming it was too cold. Quickly, he checked into a hotel and left.

Sure enough, we never spoke again. It was far from the whirlwind romance I thought it could be. This experience taught me a lot about how a situation can be more interesting than the person in it, and that it’s important to not let your conviction in the story cloud your perception of the person.

Ghosted, but in a good way

I was seeing someone for a few months and we were set for our first official date. They planned it all to surprise me. I met them on O’Connell Street with my mind racing as to what the plan was.

After rattling off a hundred guesses, they told me to wait and stand by a bus stop. Soon enough, the Ghostbus Tour pulled up.

The hostess with a mid-length bob was severely committed to her role. She put on voices, screamed at the jump scares, and gave the two of us a special look that said, ‘Aww, how nice for those gay people.’ We walked through cemeteries and even got into a coffin. It was fun, silly, and completely unexpected.

Though myself and this person were not right for each other, this spooky first date taught me that dates shouldn’t feel heavy and laden with expectation. It changed how I dated forever.

Stalemate

Soon after moving to Manchester, I met a guy at a bar. He asked me how I found living in the UK over Ireland. Among other things, I mentioned my shock that people knew very little of Ireland – especially Northern Ireland. When I mentioned British colonialism and how this affected Irish history, he replied, “Don’t take it personally, we did it to everyone.”

He went on to tell me that he’d buy biscuits and crisps and purposefully let them go stale before eating them. He’d leave them open for days or weeks.

Though we didn’t keep in touch, I think about his stale crisp and biscuit habit a lot. Some might say it’s a greater crime than colonialism itself. Maybe I’d agree with them.

This date taught me that there are certain shared understandings I need – not least of which being that stale biscuits are bad.

If you’re currently on the dating scene, check out our masterclass with cyberpsychologist Dr Nicola Fox Hamilton for a better understanding of dating apps and the behaviours you encounter on them.

Dean O'Reilly
Dean O’Reilly is an LGBTQ+ activist, sexual health promoter, psychology graduate, DEI professional and self-proclaimed ‘Little Monster’. If you’ve ever seen a 20-something filming himself taking an at-home STI test, you’ve probably seen him before.

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