There’s no denying that Alexander Stewart made 2025 his most honest era yet.
The Toronto-born singer/songwriter stepped into this bold new chapter with the release of his sophomore album What If? back in October, and it’s a deeply personal 12-track project that’s shaped by two years of reflection, growth and big life questions.
Written entirely by Stewart himself, the album finds him unpacking the roads taken, the ones left behind, and the quiet moments in between that define who we become.
“Over the course of writing this album these past two years, I found myself asking the question ‘what if?’ over and over. What if I’m stuck in this relationship? What if I lose a family member? What if I’m not enough? What if nothing works out the way I thought it would? What if it does and I can’t handle it?” Alexander said in a press release. “Making this album became an outlet for me to live with all of these thoughts swirling around in my head, and it’s the culmination of a lot of self-work, reflection, therapy, and ultimately realizing that maybe everything is happening just the way it’s supposed to.”
At its core, What If? explores the idea of alternate realities — how different life choices might’ve changed everything. That theme hits hard on one of the album’s most emotional standouts, “The Boy Almost Was.”
Inspired by Stewart’s sister, who lives a quiet, joyful life back home in Toronto, the track moves between Stewart’s current reality and the life he might’ve lived had he never left to chase music in Los Angeles.
“The song is kind of everything in my brain growing up I thought I wanted, and then I moved to Los Angeles and started making music. There’s always been that part of my brain that was like, ‘what if I never moved?,'” Stewart told Celeb Secrets host Juliet Schroder backstage at Z100’s Jingle Ball in New York City on Dec. 12.
“It’s this sliding-doors concept back and forth between my life currently and the life I would’ve lived in Toronto. The whole thing is like… who’s happier?”
It was extremely cathartic, and probably the highlight [of the album],” he continued.
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One of the project’s most talked about moments is “Friends Don’t,” Stewart’s heartfelt duet with Lauren Spencer Smith. In case you didn’t know already, the song has already surpassed 7 million global streams, and according to Stewart, was a collaboration that was as natural as it gets.
“That song’s very special to me,” he gushed. “I wrote it about a year and a half ago, and it just felt right to be a duet given the nature of the song.”
When it came to choosing Lauren, there was no formal pitch, no label meeting… just trust.
“There’s only one person on this planet that I wanted to duet with, so I just sent it to her. I didn’t even ask her if she would like it,” he revealed. “She hit me back and it happened and it was amazing. It was so organic, which is the only was it was going to happen. I feel very happy.”
The album also features fan favorites like “Here Again,” which has racked up more than 4.5 million global streams, and “Blame on You.” Notably, “Here Again” marked Stewart’s first release under his global partnership with Virgin Music Group, a milestone that allows him to continue owning his masters.
To celebrate the album, Stewart is hitting the road on the What If? World Tour, bringing his new music directly to fans across Europe and North America. The tour kicks off November 13 in Manchester, with stops across the UK and Europe before wrapping up that leg in Milan on December 3. After a brief break, Stewart will launch the North American run on February 24 in Vancouver, playing over 20 shows — including Irving Plaza in New York City and Pacific Electric in Los Angeles, where the tour will conclude on April 4.
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With What If? out in the world, it only felt right for the 26-year-old to achieve some career bucket list goals– performing on the iHeartRadio Jingle Ball Tour this holiday season.
“I’m just happy to be here, guys,” Stewart told Celeb Secrets with a grin, still riding the high of his set earlier in the day. “This is my first actual Jingle Ball run, so I’m just like.. yeah.. happy to be here.”
While Stewart may be new to the Jingle Ball family, he’s already treating the experience like something sacred. This year, he made a conscious promise to himself: to stop rushing past milestones and actually feel them as they happen.
“My whole resolution last year and continuing into 2026 is to get my head out of the ground and smell the roses a little bit,” he shared. “And just appreciate what’s happening around me. So I’ve been trying to really have a good time.”
For more on Alexander Stewart and What If?, make sure to watch our full interview below — and don’t forget to let us know what you think of the project by either leaving a reaction at the bottom of the post or by sliding into our DMs on Instagram at @celebsecrets.
For more coverage from the iHeartRadio Jingle Ball Tour 2025, click here.
