story / Ariana Tibi
photos / Siamak Abrishami
In “Cups of Coffee,” Jamie Fine captures the kind of love that never truly leaves, it simply transforms. Together with collaborators Keith Sorrells, Oscar Linnander, and Kayla Diamond, the queer Canadian pop powerhouse finds a tender intersection between heartbreak and harmony, allowing moments of emotional fracture to resolve into something even more beautiful. Whispering vivid storylines of a past love over a perfectly pure guitar line, Fine guides listeners through the power of intimacy — the shared routines, the imagined forever — before opening the song into her signature anthemic melodies. Her voice is powerful yet restrained, carrying a gentle grief that stretches from past to present.
We thought we’d get ten more years of drinking coffee
Did you think our lives would look like they do now?
I popped the question to somebody who can love me
I think you’d like her, she’s everything that I dreamed about
For Fine, the song is a soft act of gratitude. Inspired by the memory of a love you once believed would last forever, “Cups of Coffee” reflects on the unexpected growth that comes when those moments change. Now in the midst of her first U.S. headlining tour, Fine continues to cultivate spaces where vulnerability and connection can coexist. With nearly 1.5 million followers drawn to her openness, humor, and emotional honesty, the four-time Juno nominee has built a community that sees itself in her music.
In conversation with LADYGUNN, Fine opens up about life on the road, the rituals that ground her — including cooking — and the ways community can turn heartbreak into healing.
Ari:
Let’s start with the present day. I’m curious what this tour represents for you emotionally at this stage in your career?
Jamie:
It’s very emotional, period. I’m a very emotional person, I think a lot of artists probably are. And I have ADHD, and I’m a cancer. I don’t have a chance in life at not being emotional, haha.
I’ve dreamt about [this tour] for a long time and then there was this block of time where I was just so focused on navigating through all the crap. Then we played West Hollywood Pride last year, 2025. It was so last minute…it was in, like, three weeks. We figured it out, we flew out, and we played in front of thousands of people – 90% of which had no idea who I was. And I lived for that. We made them fans by the end of it. And that show itself led to us getting a US agent, and that’s how this tour came to be.
It’s been one of the more emotional experiences of my life, for sure, especially with who I get to experience it with – my boys. I’ve been playing with them for 8 years…we built this together. I won’t play with anybody else, and this tour is a representation of how far we’ve come, and everything we’ve overcome. It’s beautiful.
Ari:
Oh, I love that. There’s nothing like a solid band with that chemistry on stage.
Jamie:
Yeah! I don’t want to be this, like, pop star sitting at the front of stage with the band behind the scenes. Like, I’ve never wanted that. It feels very lonely and I want to play with people. We don’t outshine each other. We all compliment, and it’s very special.
Ari:
Why do you guys like playing in front of new fans who’ve never heard of you?
Jamie Fine:
We care deeply about the music that we play, and we care deeply about connecting with people. And if we can’t do that, then we’ve failed at our job. We’ve done that enough times that we’re very confident in that aspect. Getting in front of a group of people who have never heard of us before – and maybe even wouldn’t in another life listen to our music – to be able to convert them by the end of that, it’s so special, right?
And we don’t take ourselves very seriously. I write very emotional music, but half of our show is like a comedy skit. We just love laughing with the crowd, and including them. I’m so big on making people feel like they have a safe space in me. I love that feeling.
Ari:
Wow, that’s so beautiful. What do you think you’re gonna learn on this tour that you haven’t yet?
Jamie Fine:
Enjoy the moment. I’m always thinking ahead, I’m always planning for what’s next. And I’ve allowed myself – and made the boys remind me – to just chill for a frickin’ second and take in what we’re experiencing now. We wake up every day, just with a big smile on our face, soaking in everything that we’ve been through leading to this. It sounds so corny, but I haven’t been able to do that on a tour in a long time, if ever.
Ari:
Okay, period. Let’s get to the music. “Cups of coffee” tugged at my heart a bit because I could feel the nostalgia, the grief. I’m curious – when you wrote it – did you travel back to that grief and experience it again, or were you writing from a retrospective place?
Jamie Fine:
No, I traveled right back. I traveled right back, haha. I mean, this song is about my current partner and my ex. And my ex, I still chat with her. She’s married, you know, and we check in on each other to see how each other’s doing. I’m very close with her family, like some of the biggest parts of my life, and this song for me was celebrating that. Celebrating that not everyone that comes in your life is necessarily meant to stay forever, but sometimes those relationships can change and that’s okay. My relationship with her was very, very special. A lot of that relationship taught me how to be a partner and I want that to be celebrated, not something that’s like icky. And that’s what this song is about. Thanking her for teaching me how to love in the way that I could.
Ari:
Beautiful. What does a cup of coffee represent for you? When you ask someone to go grab one with you?
Jamie Fine:
Quality time. It’s my love language. I care deeply about spending time with people, and I think it’s a lost art. You know? Phones, FaceTime, call and text. Sitting down with my phone on silent with somebody that I love dearly and catching up. I do make an effort to do that a lot. The intimacy of sitting down with somebody and drinking a cup of coffee and just relaxing and chilling and hearing what each other has to say without anything, you know, around them. That’s very important.
Ari:
A lot of themes of being present!
Jamie:
Totally, which I struggled doing. With my ADHD, with the craziness of my life, I really struggle to be present, and that’s affected a lot of my relationships in a really tough way. It’s something I’ve really had to work on, slowing down and being present.
Ari:
Do you think that heartbreak kind of forced you to be present?
Jamie Fine: Woof. I think pain in general does. I had a really bad mental breakdown in 2016, and I vowed that I’d never get back there, and I would do the work. And I did the work. Figured out my trauma, figured out why I was the way I was, figured out why I was so stressed, figured out why I couldn’t be present. I did the work ’cause I woke up and I said, I don’t want to be this way anymore. And doing that work was the hardest thing I’ve ever done in my life. But it taught me the value of what pain can teach you, right?
Ari:
That’s important, especially in the queer community, to talk about because we experience a lot of the shadows. And everything you’re saying, to me, I’m hearing it’s worth it to go through the work and come out the other side.
Jamie Fine:
It is. It is worth it.
Ari: Speaking of queerness, your fan base has got to be emotionally invested in your music – because I’m a new fan, and I am already. So I’m curious, what is a moment with a fan that you’ll never forget?
Jamie Fine:
Ugh! I have a couple. The first one: there was a group of women who reached out to me 7 years ago. One of the women in that group had been diagnosed with stage 4 cancer. So, so, so devastating. I had just released the song “Ain’t Easy,” and they went on this one last beautiful girls trip together. They knew she didn’t have a lot of time left and I think they went to Nashville. They blared it. the whole way in Nashville. And one of the women reached out to me after she had passed, which was devastating. And she had said, “I just want to thank you…we will never forget that trip.” And I didn’t even know what to say. But it was so beautiful and I think it was the first time I realized the power of music in a big way. I’ve never forgotten that.
And then the second one: this past summer, we played a festival called Somo Fest, which is in East Coast Canada in Charlottetown. And…I’m very ambiguous with my gender; I’m a woman and I identify as a woman, but any chance I get, I’m like, “fuck, I wish I was a boy.” Haha I’m very open about that. It’s not complex to me, you know. And this person came up to me and said, “I know you’re not trans, but the ambiguity you have around gender gave me the confidence to come out as trans.” And they had talked about being suicidal the year before, and they’d listen to my music over and over again.
That represented a lot for me, with who I want to be in the queer community. I want to be a safe space for people. To see this person connect with that in a big way, it launched me into like, “Oh, I’m on a frigging mission.” This person was 15 and let’s be honest. I don’t envy any kid in this world right now, in this era. When I was in high school it was bad enough. So for them to be able to find confidence through something that they can latch onto – ugh, that’s everything. Literally the whole reason why I started doing music in the first place.
I think humans confuse the scale of complex and simple with easy and hard. When we think something’s complex, it’s actually just hard. And if we uncomplicate things, I think a lot of our problems would be solved. And me learning that lesson of like uncomplicating things in my head has made me be like so unapologetically me. I’m lucky that I got to learn that lesson but if I can help especially queer youth learn that lesson earlier than I could, I consider that a win, you know?
Ari:
Brilliant. So moving on – you’re a cook. What?
Jamie Fine:
Yeah, I went to culinary school haha
Ari:
Sick. Green flag! What does cooking give you that music doesn’t?
Jamie Fine:
Hahaha love that. Oh my god, it’s funny because it actually gives me very similar things that music gives me. It gives me art. Allowing myself to focus on something. When I’m cooking, I get to start a process – thinking about what I want to cook, getting the groceries for it, prepping all my ingredients, making something, and visualizing what I want it to look like on a plate. That process takes 6 hours, and the eating takes 20 minutes, haha. But music isn’t like that, right? It’s not that linear. Sometimes you write a song and a year later it comes out or you send it to finish production or whatever it is. With cooking, it’s a little more validating right away. It’s very calming for me.
Ari:
Love that. And, I mean, you’re feeding people with both mediums.
Jamie Fine:
100%, yeah, and again, it goes to the cup of coffee, right? Connecting with people. Who cares about anything else?
Ari:
Right! Ok, I would love to do a quick little fire round and call it a day.
Jamie:
Let’s do it.
Ari:
Fastest song you’ve ever written.
Jamie:
“If anything’s left”
Ari:
Song you wish you wrote.
Jamie:
Ooh, “Iris,” Goo Goo Dolls.
Ari:
Coffee or tea?
Jamie:
Coffee.
Ari:
Night owl or early bird?
Jamie:
Night owl.
Ari:
Share demos, or don’t share demos?
Jamie:
Share demos. I need the validation, baby.
Ari:
Intimate room or festival stage?
Jamie:
Intimate. All day. All day.
Ari:
Your sound as a flavor.
Jamie:
Whoa. That’s funny, a little spicy probably. Umami, I gotta go umami. Cause it’s everything, you know? It’s well balanced. Little bit of pop, a little bit of jazz, a little bit of rap, a little bit of R&B, umami.
Ari:
And what you’re doing later today.
Jamie:
Pool, tequila. We’re gonna spend some band time together because our L.A. show was just last night, we were gonna go to sugarfish, I think. And just, you know, have some sushi and drink some sake and just spend time together as a band and soak in everything before we head to Salt Lake.
Ari:
Yeah. Any last words?
Jamie:
I fuuuuucckkkiinngggg love you.
CONNECT WITH JAMIE FINE