Getting my first Tattoo

By: Sam D'alessandro


On leap day this year, I decided to get my first tattoo EVER. Growing up, I gathered a collection of seven different piercings but I never got a tattoo, even though it was something I was always fascinated by and at one point even wanted to be a tattoo artist. A big part of the reason why I never got one was because of my parents… It was hard enough to convince them to let me get as many piercings as I have and I figured it was mission impossible to mention getting a tattoo.



Over the past two years, I decided I was going to get one and I wanted it to be special. As and kid and even now, Winnie the Pooh has been a huge and super influential part of my life and personality. People who really know me, known the emotional connection I have to the character and how much the cartoon means to me. I decided to get the iconic cartoon honey bee from Winnie the Pooh for two reasons.


Firstly, for the longest time, I had Winnie the Pooh stickers on my closet doors and the one that stood out the most in my memory was the bee. Secondly, I wanted to symbolize the fact that even though I’m a grown adult now, there’s always a piece of my childhood that will stay with me forever. All that was left to my plan was to find an artist and tell my parents.

Back in October of 2019, I met a guy named Massimo De Carlo after inviting him to model for me for a shoot. We ended up becoming friends and I learned that he was doing a tattoo apprenticeship in Australia which I thought was so cool. Soon after that meeting, he went back to Australia. Fast forward to now, he came back from Australia and renovated his basement turning it into a super-cool home studio.


Since I had met him, I had been following his tattoo account on Instagram and checking out the work he was doing in Australia. I really liked his style and I was really digging his minimalistic stuff seeing as I wanted my tattoo to be very minimalistic. Not to mention his drawings are also incredible. When he came back, I decided I wanted him to do my tattoo, not only because he’s my friend and I’m comfortable with him but also because I really appreciate his talent and wanted to support him in his tattooing career.



His brand is called Dark Passenger Tattoo and he tattoos out of his home studio in Mississauga and out of a shop in Toronto called Smoke Signal Designs. I got my tattoo done in Mississauga which was awesome because I got to see the studio that he designed. The studio is super clean looking, painted white with black accents and it's decorated with retro comic books, cameras, and other items.


Since this was my first tattoo I was obviously nervous but Massimo was quick to assure me that everything would be fine and he communicated with me ahead of time how it would feel, how long it would take and how small we could make it which made me very comfortable and confident with the process. When it came time to actually do the tattoo, I was unsure about the placement and he was super patient with me, placing it until I was happy with the position.



The tattoo took about 15 minutes for him to do and he was very gentle and reassuring the whole time, making sure I was okay. It was surprisingly way less painful than I expected considering I was getting it on my ribs and it was actually a pleasant experience. I’m absolutely obsessed with the outcome; it was exactly what I envisioned and I would definitely go back to Massimo again in the future. If you’re looking to get your first tattoo or add to your collection, be sure to check out his page on Instagram!


Another huge thank you to Massimo for making my first tattoo experience amazing.

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