Raised a born again Christian, Lily Frost left home at eighteen. Curious what an alternate life would look like, she attended university in Montreal and met artists, writers and thinkers, and explored worlds of foreign film, philosophy, erotica and travel. She never turned back.

Now an award-winning singer-songwriter with fourteen album releases under her belt, her music touches on topics like secrets, stonewalling, forest fires, feminism, desire, motherhood, dreams and the intriguing entanglements between men and women. Her latest album, Retro-Moderne, came out this June. 

We caught up with Lily this week. 

SDTC: Describe your dream vacation/getaway scenario:

LF: Barefoot, tall open windows, overlooking the ocean, with my lover, red sands, dry heat, espresso, wine and natural hot springs…oh, and a piano.

Who/what is commanding a lot of attention in your life lately?

My kids, my music and my clandestine lover.

What have you learned about yourself in the past year?

We are all responsible for our own happiness.

Actively working on and learning to break cycles of codependency across the board.

If you give 100% in art, it’s worth the risk. Just get over self doubt and go all the way. Trust self.

Say what ya mean, mean what you say, but don’t say it mean.

One fun, little-known fact about you?

I can speak some Arabic from singing on a ship moored in Zamalek Cairo when I was twenty. Mumpkin means maybe. (A cute word, not sure how to spell it.)

What book/film/show have you really connected with recently, and what about it appeals to you?

Virgin Cure and Witches of New York by Ami Mckay, and the Handmaids Tale series, revealing injustices toward women in a poetic, graphic, emotional, artistic and revolutionary way.

What’s the worst piece of career/life advice you’ve been given?

“Wear a mini skirt and look ‘just fucked.’”

What is your motto at the moment?

I have a few affirmations, but they are private. I love this Gloria Steinem quote: “The truth will set you free but first it will piss you off.”

My favourite quote since forever is by Robert Browning: “There is an inmost centre in us all, where truth abides in fullness;… and, to know, rather consists in opening out a way where the imprisoned splendor may escape, then in effecting entry for a light supposed to be without.”

Any goals/plans for summer?

Get out of the city. Get up north. Make fires, swim, write, breathe fresh air. Sell a million albums.

What are the qualities you like least & most about your parents?

I like my mom’s humour, not her micromanaging. I like my dad’s generosity and kindness, not his impatience and negativity.

Rewind five years. What advice would you give yourself?

Well, when people want divorce they come to me sometimes and I say, “Go on a vacation.” Better to be selfish and indulge in a solo week of decadence than split up a family. However, I do not have regrets for the decision my ex and I made.

What is the most courageous thing you’ve ever done?

Had babies. It is unbelievable on so many levels. And, going down the black diamond ski hill in Panorama, BC, when I was twelve.

What childhood memory makes you laugh out loud?

My brother and I turned a neighbour’s abandoned garage into a clubhouse and we bought a heater for winter. Matt turned it on and lit it and it exploded. He turned around and his eyebrows were singed off. Of course we were scared, but we laughed our heads off.

What unnecessary object would you love to own?

A salt water hot tub fuelled by fire with strong jets.

What tip, technique or hack has made your life better in the past year?

Portable Bose speakers. The parking app on my phone.

Which issues do you wish people took more seriously?

Emotional intelligence, domestic violence and teaching kids cultural arts appreciation and understanding in schools.

What outfit do you wear more than any other (your uniform, basically)?

Yoga pants, tank top and a poncho with Blundstones.

Who/what has surprised you lately, and how?

Greta Thunberg for speaking up and being so clear and brave about climate crisis. Speaking to the UN on the level. Holding people accountable.

When you look back on your life, are you at where you thought you’d be by now?

I always knew I’d have two kids, but I never planned to be divorced. I thought I’d be in California by now. I love Georgian Bay and am close to the family cottage, which is a great rejuvenator. Everything happens as and when it should, and there’s lots of life yet left to live. I didn’t know where I’d be at but I didn’t think I’d be in Toronto this long. My children are here for now, so it’s my home and I turn winter into a cozy fest to cope. It works. The fine art of coziness.