My pumpkin carving tradition: messy, funny, and full of heart

Pumpkin carving wasn’t part of my childhood. In Bulgaria, Halloween just wasn’t a thing back then. But in 2016, that changed – thanks to a spontaneous idea, two pumpkins, and a very patient ex-boyfriend.

We had just come back from playing pool when we carried those pumpkins into my little apartment in Aalborg. “I’ve always wanted to try this,” I told him, half excited, half convinced I’d make a mess. (Spoiler: I did.)

That weekend sparked a tradition we kept going for years, even as life changed around us. No matter where we were, we always made time for pumpkins, carving tools, and a whole lot of laughter.

pumpkin carving tradition
Our pumpkins, fall 2023

Table of contents:

My first time carving a pumpkin

That Halloween week in 2016 started with a little surprise. My ex and I had spent the day playing pool, and at some point, I told him how much I loved the idea of carving pumpkins. It always seemed fun and creative, something I’d missed out on growing up in Bulgaria, where Halloween wasn’t really a thing.

Later that day, we showed up at my apartment in Aalborg with two pumpkins in hand. He had made up his mind: we were going to try it. It was new for both of us, which made it even more exciting. We looked up simple carving ideas, picked basic designs, and got to work.

That’s when the chaos began.

I like things neat and clean. Pumpkin carving is neither. We had tools scattered everywhere, seeds on the floor, and sticky orange guts clinging to everything. I tried to scoop mine out as carefully as possible, while my ex dove in elbow-deep like he was born for it. Meanwhile, we kept switching knives, realizing none of our kitchen ones were quite right. (Spoiler: they weren’t.)

I chose a classic face, triangle eyes, and a smile, but it didn’t turn out quite as planned. The triangles looked more like leaves, and the smile was lopsided. Honestly, it was a mess. But I was laughing the entire time.

He, of course, nailed it. His pumpkin came out funny, balanced, and actually looked good. He’s great with detail – he paints tiny gaming miniatures and even adds fur and cloaks to them. So carving a pumpkin? Right up his alley.

The next day, still in the Halloween mood, we decided to get a third pumpkin. This time, we had a better idea of what we were doing. He took the lead again, and the result was our best yet.

That messy, silly weekend quickly became one of my favorite memories, and the start of a tradition neither of us realized would last so long.

pumpkin carving tradition

Turning a one-time thing into a tradition and keeping it alive

After that first messy weekend, it was clear: this had to become a thing. So the following year, we did it again. And then again. For years, it became our fall tradition — something we carried with us through moves, studies, and different chapters of life.

Each October, whether we were in Sweden, Denmark, or Italy, we carved pumpkins. It was never about the perfect design. It was about slowing down and doing something creative, with no expectations and no rush.

Our pumpkins may not win awards, but they always win laughs.

Over time, the little details around the tradition grew too — planning our pumpkin hunt, choosing shapes, imagining silly faces. Finding the right pumpkin felt like a ritual.

Finding the right pumpkin is serious business. It’s like dating – but orange and round.

And when we discovered a carving kit at Flying Tiger, it changed everything – cleaner cuts, more details, and less knife drama.

Even during his first PhD year in Sweden, we made it work. I’d visit near Halloween, we’d carve pumpkins, eat something cozy, and binge Stranger Things in the dark with our jack-o’-lanterns glowing nearby.

watching stranger things on halloween after carving pumpkins during the day

Halloween isn’t a big deal in Italy, but we made our own version of it. Kitchen table, tools, candles — instant fall magic. Every year, when we lit the candle inside the final design, we’d smile. Goofy or great, it didn’t matter.

Because back then, it wasn’t just about Halloween decorations — it was about connection, laughter, and creating a tiny moment of joy in the middle of autumn.

Pumpkin carving tips for newbies (from someone who started with a mess)

If you’ve never carved a pumpkin before, don’t worry. I started with leaf-shaped eyes and a crooked smile, and I still had the best time. Here are a few simple tips that can make your first pumpkin carving way more fun (and a little less chaotic):

  1. Choose a smooth, firm pumpkin: look for one that sits flat and has an even surface. It’ll be much easier to carve, especially if you’re going for a design with details.
  2. Cut the lid at an angle: when you cut the top off, tilt the knife slightly inward. That way, the lid won’t fall inside once you place it back on top. (Yes, I’ve learned this the hard way.)
  3. Scoop it out well: the cleaner the inside, the better your candle will sit and glow. Use a spoon, an ice cream scoop, or even your hands – whatever works best.
  4. Sketch your design first: use a pen or a washable marker to draw your design before you start cutting. Simple shapes like triangle eyes and a toothy smile are perfect to start with.
  5. Use proper tools if you can: a basic pumpkin-carving kit makes things so much easier. The small saws and pokers help you make cleaner cuts without struggling with kitchen knives.
  6. Take your time: pumpkin carving isn’t a race. Play some music, light a candle, and enjoy the process. The mess is part of the fun!
  7. Light it up safely: if you’re using a real candle, make sure there’s enough room inside. Or skip the flame and go for a small LED tealight – it’s safer and lasts longer.
carving a pumpkin for halloween

And the most important tip? Don’t aim for perfection. Aim for fun. Your pumpkin doesn’t need to look like a masterpiece. If it makes you smile, you’ve done a great job.

Wrapping it all up

Looking back, I never expected that a random October afternoon in 2016 — just two pumpkins and zero carving skills — would turn into a tradition that lasted years. But it did.

Even though life has changed and we’ve gone our separate ways, this tradition still means something to me. It reminds me that small, simple moments can become the ones that stay with you.

Whether you’ve carved pumpkins forever or you’ve never tried it, I hope this post inspires you to create a little tradition of your own.

Because honestly? The smallest moments often turn out to be the ones that matter most.