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How To Suck At Romance

Why my catastrophic attempt to win someone's heart still makes me want to die fifteen years later.

By Matt UnderhillPublished 3 years ago 9 min read
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Being a teenage boy is hard, especially if you’re a lovelorn romantic.

Back in the heady days of 2006, in a pokey little town about an hour outside of London, a gangly, spotty, 15-year-old boy was in love. That boy was me.

The girl in question was, to me, perfection in a My Chemical Romance hoodie. She was tall, beautiful, funny, kind and caring. My adolescent, angst-filled brain saw her as a goddess. She was my Helen of Troy, and I would have sent my navy around the world for her... had I owned one.

The only problem was, as you’ve probably already guessed, she only saw me as a friend. And we were friends, too - I was never one of those guys who sidled up to girls and pretended to be their friend, only to then chance a snog at a disco and lie to his friends about getting to touch some boobs. I loved her company for its own sake. But, to a teenage boy with limited emotional understanding, the jump from friends to lovers for eternity was not a large one.

“If she likes being around me,” I mused, “Then she must want to fall madly in love with me too, right? We get on so well that it must be love, deep down.” I’m ashamed to say that my desperately wonky thinking even led me to believe the following, desperately pathetic idea:

“She’s probably just making me work for it so that when it does eventually happen, it’ll be all the more romantic.”

Now, at the ripening age of 30, I do of course recognise how problematic this is. At the end of the day, this is about consent. A line had been drawn in the sand by the object of my infatuation and I was refusing to acknowledge it. What I will say, however, is that there was never a single iota of cruel intent or maliciousness about my infatuation - just a puberty-powered, half-baked idea of what love is and absolutely no idea on how to act on it.

And, to be fair, I had learned about love through stories, not real life. With no brothers or sisters to talk to and a general teenage embarrassment about asking my parents, my teachers in the art of romance were the likes of James Bond, Anakin Skywalker, or essentially any male character from a Disney movie. And what are the two common themes of “romance” in these stories?

Persistence, and/or a grand romantic gesture.

Sadly, after persistence failed, that idiotic, teenage moron tried the latter. And it went spectacularly wrong.

By Kelly Sikkema on Unsplash

February 14th, 2006. The apple of my eye needed to buy new jeans, so I said that I needed to pop into town, too.

Reader, I did not need to pop into town. I just wanted to be near her. Sad? Check. Desperate? Check? The makings of a future incel? Double-check.

Also... cute?

...No. Absolutely not.

Anyway, maybe out of pity, maybe out of genuine enjoyment of my company despite… everything, she said I could come along.

After grabbing some food and sitting next to the bins chatting about teenager stuff (who’d recently snogged who, how much trouble someone got in for drinking their dad’s vodka, the latest emo track we’d downloaded from Limewire, etc. etc.), she told me to wait while she went to get the jeans.

So, being the obedient little pet that I was, I waited by the bins while she headed to Topshop. But then I realised.

“Oh my God, it’s February the 14th...

“VALENTINE’S DAY!”

I immediately panicked, as any sane person would do. This was the perfect opportunity for me to play my ace, seal the deal, embark on the grandest romantic gesture the world had ever seen, and I hadn’t thought of a single thing to do.

“I can’t let this chance slide,” I thought. “If I do, then who knows might sneak in and win her heart before me! Oh, woe betide me and my foolish heart.”

Or something similar, at least. I was a bit melodramatic and weird, as you've probably gathered.

In my panic, I got up from my perch next to the bins (ignoring the old gum that I’d sat in that was now stretching from the brickwork to my trousers) and looked for a shop where I could buy a present.

Flowers. Chocolate. A cute little present that was meaningful and funny. All respectable, mutually agreed options for romantic gifts that could be taken as a thoughtful touch while not being over-the-top. Sadly, none of these things entered my mind. In my mania to find something before she returned, I practically sprinted into the nearest post office.

Yes, reader. A post office.

I scanned the store for what I could get her.

“A teddy? No, too much. OOH, a massive teddy. That might... No, still too much. Flowers? Pfft, nah, too cliché. Oh God, oh God, what do I do, what do I... Hello.”

My eyes settled on the gift.

“Perfect.”

To this day, I’m not entirely sure what in God’s name I was thinking. Even now, fifteen years later, I am still occasionally reminded of my choice of “romantic” Valentines gift and the hairs on the back of my neck stand on end. But while I still get shivers from my choice of gift, what happened next is what awakens me in the middle of the night in cold sweats.

I pocketed the gift, elated that I would, finally, be with the one I loved. There was no way, no way, she wouldn’t love me after this.

She returned from buying her jeans, and I acted like I’d waited there, by the bins, the whole time, smug in the knowledge that her world would soon be turned upside down. We lived around the corner from each other, so she suggested that we go back to my place for a bit until her mum finished work.

I immediately formulated my plan. While we were at mine, I would slip the gift into her jacket pocket, so that after our afternoon of hanging out together, she would get back to hers, reach into her pocket, discover her gift and realise, finally, how much she really loved me.

Urrghhh.

And so we headed to my house, went up to my room and continued talking teenagery things, me with a colossal grin on my face and feeling very pleased with my scheme. When she went to the loo, I moved like a ninja past the bathroom door and down the stairs. I found her jacket, slipped the present into her pocket, and glided back up the stairs and into my room. The stage was set. Everything had fallen into place. It was time, at last, to win her heart forever.

Eventually, her mum arrived and started chatting with mine. After a good natter, we were called downstairs and said goodbye to one another.

“This is it... This is it...”

She went to put on her coat. Our mums shared some final pleasantries and they both turned and headed for the door.

“It’s all coming together...”

And then I realised that my long-suffering “soulmate” almost exclusively walked with her hands in her pockets. Which is why, when I saw her raise her hands to tuck them in, I immediately knew what was about to happen. My eyes widened in horror as I realised what I had done.

“Oh no. Oh no, no, no, no, no...”

She was going to find it now, in front of me. And my mum. And her mum. It was at that moment that I also realised that I had purchased the single worst Valentines present in eternity.

“Oh, what’s this?” she asked aloud, nonchalantly.

A profound sinking feeling started enveloping every fibre of my being. I watched in slow motion as she slowly pulled the gift out of her pocket, looked deeply confused, briefly horrified, and then, finally, sad.

She held the gift in her hand and looked at me.

It was a small, red, heart-shaped cushion in a box similar to an engagement ring, that read, “You’re Mine.”

Yes. Really.

I hope I needn’t tell you that I wanted to ground to swallow me whole. I wanted to never have existed, for some bizarre cosmic event to set fire to me where I stood, or to just immediately drop down dead and be done with it all.

We stood there. Me, her, her mum and mine. No one said a word for what felt like an hour.

Finally, she mumbled “Thank you,” as kindly as she could muster, and she and her mum left my house.

My mum turned to look at me with a sympathetic look in her eyes and said, “That was a nice idea,” then turned into the kitchen, presumably to die laughing. I stood there, red as a letterbox, seething at myself.

“Why, Matt, did you think that would work? How on earth did you think that would be a good idea!? Did James Bond buy Natalya Simonova a miniature pillow? No. Did Anakin Skywalker buy Padmé Amidala gifts with weird, controlling messages on them? ...Actually, that does sort of sound like the thing he’d do, but does that mean that you should do it, too?! No! Could this possibly, ever, have been a good idea?! NO.

“What were you thinking?!”

I went back up to my room and sat on my bed, in silence, for half an hour. The wool had finally fallen from my eyes, and I realised that I was, in truth, pretty rubbish at this whole romance thing.

So yes, while the whole sorry episode was pretty horrific and genuinely still makes me want to implode into a singularity of embarrassment when I think about it, it was a learning experience. Being considerably more developed than I was, the girl later very graciously told me that she was grateful for the gift, but explained that it wasn’t really that romantic and was actually a bit creepy. I knew all this already, but sat and let her tell me anyway.

And no, there never was the Disney+, fairytale ending where we ended up together anyway. But that was sort of the point, and also the lesson I learned that day: love isn’t about fairytale endings or grandiose gestures. Love is a lot tougher than that. It would be a long time later that I learned that while persistence is vital to love, it’s not in the wooing, but in the making it work where it counts.

And love is all the better for it, I reckon.

These days, I tend to buy my girlfriend flowers. Cliché or not, they’re a damn sight better than a heart-shaped cushion with “You’re Mine” written on it.

Embarrassment
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About the Creator

Matt Underhill

Politics geek / video game afficianado / occasional exerciser. Flag-bearer for reducing stigma around male mental health.

Part-dog.

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