Interview with Musician Regina Song (@sleepyreggy)

This month, our Editor-in-Chief had the pleasure of sitting down and chatting with Regina Song, a rising Singaporean singer-songwriter sending ripples throughout the industry. After the release of her debut album fangirl, Regina has gained over 2.3 million listeners on Spotify, with her viral song ‘the cutest pair’ having amassed over 51 million streams as of early September 2025. Moving forward, Regina is set to release an album later this year, with her latest single ‘Before I leave’ captivating hearts worldwide.

In this interview, we delve into the emotional complexities of her music, songwriting, and inspiration, in addition to opening up about personal challenges, experiences, and embracing the highs and lows of love and community.

Hi, Regina! What is your favorite song that you've created, and why?

Regina decided on “Heartache Frenzy”, a fan favorite from her debut album. Instead of her usual approach with piano or guitar, she wrote random chords on pieces of paper, placed them in a bowl, and drew four at random to build the foundation of the song. Afterward, she composed using GarageBand rather than her usual instruments.

“I love how the song turned out because the flow came so easily,” she says.

Your recently released single, 'Before I Leave', is a beautiful and bittersweet track. What was your thought process and inspiration behind creating this song, and what thematic elements can fans expect in your upcoming album?

'Before I Leave' was written during Regina’s time at a summer exchange program in Boston in 2023, shortly after her first breakup. It was a period of rebellion and trying things that felt "un-like herself”, such as using dating as a distraction. The song questions why people chase love in places they'll never return to, with Regina mentioning that it captures that 'lavender haze' of fleeting romance. She wrote it in a practice room at Berkeley College, embodying that contemplation of love abroad.

“The essence of the song is that rebellious face we all put on after a breakup,” she admits.

In her upcoming album, fans can expect these themes to expand—from teenage love to more mature perspectives, dealing with heartbreak, doubt, and ultimately growth. The album documents Regina’s entry into her first relationship and the recovery process that followed, capturing both the highs and lows of all things love.

Your upcoming album is scheduled to release in late 2025. If you could describe the album in one word, what would it be?

Growth. This album represents Regina’s evolution from the naïve teenage love she explored in 'fangirl' to more mature relationships and broader connections—not just romantic, but with friends, mentors, and herself. Whereas 'fangirl' was about falling in love from afar, this new album is about being in love, experiencing doubt and heartbreak, and ultimately taking power back from being a hopeless romantic.

“It’s not just about romantic love; it’s about relationships with people and navigating life after high school,” she says.

Our audience is largely composed of young creatives ages 13-25. What practical advice—whether about songwriting, production, or leveraging social media—would you give to our audience who hope to turn their passion into a career?

Regina gave us four key pieces of advice that helped her navigate her early career. Firstly, focus on skill over outcome. Don't focus on the result; focus on being good. Second, release everything. Give every song a chance—even if you're unsure about the fear of judgment. Thirdly, detach emotionally from your work. Treat finished songs as products rather than personal extensions.

“Don’t focus on the result; focus on being good.”

Finally, create external triggers for action. Find motivations like deadlines or feedback systems to combat procrastination and perfectionism. Remember that understanding algorithms is important, but don't let them control you.

“I faced challenges when starting because I was too focused on what the algorithm favored, but I found my breakthrough when I focused on creating authentic content that felt true to me.”

Our community at Chartium has a strong Singaporean presence. I'd love to hear about your own background—how has growing up in Singapore influenced your creative style and the ideas you're passionate about?

Regina talks about how Singaporean culture emphasizes competitiveness and hard work, which creates both tension and opportunity for artists. She mentions how the local music industry is small but tightly-knit, with strong mutual support among artists. She’s delighted at how the Singaporean music industry is growing rapidly nowadays.

“We are born to be competitive, but art should come from a place of wanting to create.”

Growing up in Singapore, Regina mentions how she faced pressure to pursue traditional careers, but she’s been fortunate to have supportive parents who sent her to piano lessons at age 6 (though she didn't enjoy them initially!). Later on, she eventually enrolled in the School of the Arts as a classical pianist, and that immersive creative environment during her teenage years gave her opportunities to write, sing, and play music that shaped her artistic identity. She also adds on to how Singapore’s multilingual environment has given her exposure to various music genres (K-pop, Mandopop, and Western pop) has given her a diverse musical palette that she blends into her own style.

Your debut album fangirl is described as a "literal documentation of your growth as an artist," capturing emotions from delusional love to frustration. How did you approach blending diaristic storytelling with musical experimentation across genres like pop, R&B, and indie?

Regina say that her approach to fangirl was intentionally emotionally focused rather than genre-focused. She started with bare-bones chords and lyrics that felt true to my experiences, then allowed collaboration with my label to explore new sounds without over-thinking. Angsty songs received more upbeat production, while emotional tracks got slower, sadder tones.

“I've always been inspired by how Taylor Swift creates universes in her songs.”

Your music resonates globally, with "the cutest pair" becoming a TikTok sensation and an anthem for young love. How do you balance authenticity with the pressures of viral trends, and what message do you hope to convey to youth about self-expression and embracing vulnerability?

Regina believes her balance comes from prioritizing personal feeling and song quality over chase-the-trend pressure. She write songs guided by emotion first, then reviews her list to pick tracks that best fit the album. Additionally, she mentions how quick trends come and go, so it’s important to stay authentic and true to yourself.

“As long as I keep staying authentic and put out work I’m proud of, my listeners will resonate with it.”

Regina’s message to youth is that vulnerability is strength. Watching someone you care for deeply move on unexpectedly can be confusing and complex, but processing these emotions is part of growth. Regina hopes that her music offers peace and comfort to listeners experiencing similar feelings while helping them process their emotions.

You've spoken openly about facing personal challenges during the peak of your success with "the cutest pair," including a breakup and management changes. How did these experiences shape the emotional depth of your upcoming album?

After reflecting, Regina believes these experiences were fundamental to the emotional depth of the new album. During that period, she had to watch her first love move on and see someone new, turning into someone that she couldn't recognize. The combination of frustration, disappointment, and anger, ultimately transforming into concern, drove her to write "Fairy" in one night, demonstrating her power in taking back from heartbreak . Meanwhile, the management changes taught Regina to trust her instincts more deeply. The new album explores these life changes through a mix of upbeat and sentimental songs.

“It's okay to not be okay sometimes, and that growth often comes through pain.”

Where can you see yourself in the next 10 years, and why? If you could say something to yourself in the next 10 years, what would it be?

Regina sees herself primarily as a touring artist—she absolutely loves live shows, meeting fans, and traveling. She aims to perform at major festivals and continue releasing projects that resonate with both herself and listeners. Regina is also exploring launching an apparel line linked to her music brand—merchandise feels like a fun extension of artistic identity. On a personal level, Regina mentions that she hopes to be married by age 31, desiring a life that feels sweet and balanced alongside her music career!

“I hope she (me) is happy and at peace with the decisions, like the decisions she has made and that whatever happened happened for a reason.”