Writing has always been a part of Orillia-based singer-songwriter Cassie Dasilva. She started at a really young age writing poems in her fuzzy pink diary. Just like her writing now, Dasilva used lived experiences as the fuel for her creative process.
“It started as dealing with things like fighting with my siblings or my parents divorce, then eventually it changed to boys until I finally got into writing about rejection and all of that stuff,” she said.
Writing wasn’t the only way Dasilva channeled her creative side. She started playing piano at the age of six before getting a guitar in the eighth grade. From there, her music career took off.
“I kind of started putting the music and lyrics together in the eighth grade. Then in high school I started doing coffee houses and open mics and they seemed to like what I was doing so I kept making more. That’s when I was really sharing my own songs on youtube and it just kind of evolved from there.”
Dasilva went on to apply to Berkley on a whim for their songwriting program and was accepted. While her path took her a different way educationally, she didn’t stop making music.
“I ended up going to school for audio engineering and recording to learn that side of things. It actually proved to be pretty beneficial because those skills are very transferable into writing and recording. At the same time I was writing, doing songwriting camps and also recording my own music, and it all just kind of spiralled from there.”
Since the release of her breakout single “Unsolicited Contact” in 2021, Dasilva has amassed over seven million career streams. Her debut EP “Enough” received recognition from EARMILK for its vulnerability. In 2025, Dasilva was selected for the inaugural SOCAN Foundation x TuneCore Nashville Residency, where she expanded her creative network.
“I’ve spent a little time writing in Nashville and every time I go there I feel inspired by everything going on and just the way music is there,” Dasilva said. “It feels like the song is what comes first and what’s most important.”
Dasilva said that she got to stay at the SOCAN house during her time in Nashville which she described as a “great little spot.” There she was able to make even more connections in the world of music and even got the chance to play at a legendary cafe.
“I had already made some connections which was great. A friend of mine actually invited me to play at the Bluebird Cafe which was a bucket list item of mine so that ended up being a really cool experience.”
Childhood Idols And Present Day Inspirations
Like many others, Dasilva grew up a Swifty. She said she remembers hearing Taylor Swift’s music for the first time and realizing in that moment that you could talk about vulnerable topics in songwriting.
But that wasn’t the only musical influence Dasilva had in her life. She said she would also listen to John Denver, Shania Twain, and even Cher, meaning she was exposed to a wide range of different music.
“I think that was important because it helped me find what really inspired me, which was lyrics,” Dasilva said. “My parents had quite a vast CD collection and I would just lay on the living room floor and read the little booklets or read the lyrics. I just found that part of it so neat which is probably why I’m such a lyric oriented writer.”
In her more recent writing, Dasilva has found inspiration from the raw storytelling and organic sounds of the female singer-songwriters from the 90s to the early 2000s.
“Recently I’ve been leaning into artists like Cheryl Crow, Liz Phair, and Alanis Morissette. Basically women who are putting it all out there and writing about their stories,” she said. “Those stories need to be told and you know there’s a reason so many people like them because they can speak to the female experience.”
Letting Experiences Become The Story
Dasilva’s newest single “Never Saw Me Naked,” which was co-produced by Toronto producer-songwriter duo thankyouthankyou, is another example of a story about the female experience.
After running into her ex-boyfriend at the local fair and having to pretend like everything was fine, Dasilva knew she had to make a song about it to tell the story.
“It’s a funny thing being in a small town because you do run into a lot of people, and occasionally you run into someone who maybe at one point or another saw you unclothed,” Dasilva said.
“Pretending I didn’t have that past with someone was so jarring I knew I had to write about it. While writing it we all kinda in the room were like ‘oh yeah that’s such a crazy experience’ and I wasn’t the only one who’s had it, so there’s got to be more of us.”
While some may think interacting with an ex like they’re any other old friend is normal, Dasilva said she feels the complete opposite.
“I think it’s this expected thing, especially in a small town, to be cordial and something to be proud of that you’re [still] great friends, but I could never really get past it. This song is about that person making small talk and that feeling of ‘is it casual to you? Does it really mean nothing because I don’t know how you’re talking to me normally.’”
Dasilva said that after not putting out any music since her last EP in 2024, she is excited to be releasing something new for people to hear.
“It’s taken me a while to kind of find my sound and figure out where I wanted to go next. I’m glad I took the time because I think I’ve really gotten down to the kind of music I always saw myself making and I’m excited to share that with other people.”
You can stream “Never Saw Me Naked” here.
