Dating: My Experience & What I've Learned


Kyle* (name changed) was two years older than me. He had a golden heart and the jaw structure that only existed in teen drama shows. Although he claimed to be a heterosexual male, we often slept in the same bed and found ourselves spooning. He liked to cuddle and it wasn’t long before we found ourselves in a two year relationship. At one point we were even engaged. The relationship came to an end when I found him texting a girl while I lay next to him, pretending to sleep like some sort of crazy psychopath, hell bent on spying and catching him out. I’m glad I did. Kyle and I no longer speak and he is currently dating a lesbian.

Timothy* (again, name changed) was a film maker and writer I met in college. We formed a slight ‘bromance’ over our creative mediums and one night he came out of the closet to me by making me guess what he and Elton John had in common. Since he didn’t have a ginger bowl cut or sing regularly on a piano, I guessed correctly that he was gay. We enjoyed a relationship together for a while, the worst part of it being the fact I had to fake pleasure during intimacy seven times out of ten, but we had a good bond and that was more important to me. We ended up breaking up not long after due to a few choices I decided to make back then. We’re still friends, and he is currently dating a girl. Apparently he’s heterosexual again. Who knew that could happen?

Shane* was a womanizer. He was constantly seeking the attention of women and always on the lookout for intercourse with them. We were good friends and really close. So close in fact, that we found ourselves in an intimate position one night and then started a relationship soon after. He was dangerous, broody and a complete mystery and for some reason it attracted me to him on a higher level. It wasn’t long before he strayed from the relationship and cheated on me. It was heartbreaking, but at the same time, completely liberating. There’s something quite empowering about someone bowing down to you after they’ve been caught. We’re not friends anymore and the last time I checked, he’s single, friendless and miserable. Karma, B**CH!!!

These are just three of my relationships, and these are the ones that have stuck with me. They’re the ones that have changed me in one way or another or taught me a life lesson. They’re the ones I will cherish because I genuinely felt something for them, something I thought only existed in rom-com’s and chick-lit. But it also says a lot about my ‘type’ everytime I think about it. I always seem to go for the more masculine male, the one who presents himself as tough and strong. The one who is a little bit dangerous. A bad boy. Someone who my friends question me about. As an investigative reporter, I’m drawn to mystery and solving things, and it doesn’t stop with crime. It’s people, too. I like to think I could figure these boys out, but I couldn’t. Especially Shane. Shane was an eternal enigma. I couldn’t do it anymore. There wasn’t a mystery I couldn’t solve.

But after all these guys, I took some time to myself. Time to figure out where I would go next. I’m still in the process, and during it, I decided to jump in to the world of online dating. I’ve always met my previous boyfriends through friends, or in a dive bar. Places which I still look back at as ‘the place it all began’. Happy memories. It created a hatred for the future. And by future, I mean logging on to an account and scrolling through photo’s of men who could be potential dates. I find it a little bit freaky and quite unnatural. Mainly because we look nothing like our pictures, we come across as if we don’t want to be on the site and when asked on a date we usually panic. Is he a crazy murderer? Am I being Catfished? Is this a friend trying to wind me up by creating a profile of a hot guy they know I’d fall for? Questions ran through my head at a million miles per hour and I couldn’t slow them down. They almost made me cancel the date invitation from pure paranoia, but upon having a heart to heart with one of my close friends, I decided to jump right on in with both feet and before I knew it, I was on my first date in nearly a year.

Harry* met me one evening in my local pub after we swapped text messages, mainly conversing about horror movies and the current episode of Doctor Who. Meeting him in person for the first time was strange, mainly because when I find myself in an uncomfortable situation I turn into the most socially awkward person ever. I talk about sea creatures, I develop a stutter, come out with strange word combinations and sometimes I even sing. All of this happened on this date and luckily he found it slightly amusing. The date went on for three hours and after it finished, he drove me home, giving me a kiss on the cheek as I left. It was a successful date and although I began to develop some form of feelings for Harry, we never got around to meeting again. Mainly because I’m the worst texter in the world and gradually we ended up messaging each other once a week until the conversation got dry. I lost faith in myself and the world of dating.

But I decided to not give up and try again. I met Percy* on Plenty of Fish. He was a banker with a taste for spontaneity and adventure, something I was attracted to profusely. We decided to meet up for a coffee and when we did, it was one of those rare occasions where his photos didn’t do him justice. He was even more beautiful in real life. It was probably because he was wearing his work uniform which was a suit, and we all know how good men in suits look. They’re even more desirable if they smell nice, which Percy did. We talked about our career’s as an ice breaker. I explained I was a writer and blogger looking for my big break while writing a novel on the side, and he was a banker in one of the big banks in town. I’d awkwardly brought up how I’d seen him before while I was sorting out my account details and took a fancy to him. He laughed, and when our conversation was over, he straight up asked me if I wanted to go back to his place for sex. I politely declined his offer and made up an excuse to leave involving an undercooked turkey. Embarrassing but effective. I haven’t heard from Percy since.

More recently I experience my first double date. I began to talk to Paul* on Grindr (don’t judge me, I’ve spoken to some cool people on that app) and soon after we began to exchange text messages and Snapchat images. He was a breath of fresh air, someone who I actually enjoyed texting. He was nice to talk to and I didn’t feel like I had to make conversation because it never got awkward. The moment came where we decided to meet up and for some reason, I was a bag of nerves. I was so nervous in fact that I decided to turn the evening in to a ‘double date’! My friend Katie LOVED the idea so much and phoned her love interest, Matt, to come down to join us. Katie and I headed over to the coffee shop an hour beforehand. I was drowning myself in latte’s while Katie nibbled on a bag of chicken. There was no denying that I was extremely nervous and anxious for no apparent reason, but at the same time, excited. The time came where Paul arrived and I attempted to be confident and ‘together’. Unfortunately that plan backfired and I turned into an awkward mess. For one thing I was wearing a hoodie consisting of a popular comic book character while Paul looked dapper in a nice shirt. I felt underdressed and out of place. That changed when we began to engage in conversation and when Matt arrived, we were officially a foursome.

I don’t know why, but being
on a double date, sat there around a circular table in that moment made me feel like I had accomplished something. That I had finally done something that I’d heard most twenty-somethings talk about as if it was normal. Then I realised that double date usually consisted of two couples doing something, not one couple and two strangers. It wasn’t awkward, apart from when I wanted to ask so many questions and I froze. I asked him twice how his day had gone because I turned into a socially awkward idiot with no sense of memory. It was more laid back since I had my best friend sitting to my left, comfortably sipping on her latte. I did feel quite bad since I dumped the ‘double date’ idea on him an hour before we were supposed to meet, but then again, spontaneity is something I live for, and I hope he enjoyed despite the night taking the four of us to unexpected places. The Halloween section in a local supermarket, for example. I don’t know if me and Paul will meet again. I have a fear of asking for date number two and experiencing rejection, so I need to pluck up the balls to do that. But for what it’s worth, double dating was definitely an experience.

So I’ve learned a lot from my time as a serial dater. I’ve learned to stop looking for a specific ‘type’ and meet new people. I’ve learned to stop over-thinking and jump in to things with both feet and most importantly, I’ve learned that Shane, Kyle and Timothy were just moments and memories and that I don’t have to hold myself to any standards based on what they thought of me and what I thought of them. Everyone is different and if you learn to experience one anothers lives and opinions, something can be created which could be unforgettable.

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