Desmond Tan is no stranger to covers; they’ve punctuated every chapter of his life. From his early days in the industry, where youthful energy and ambition defined him, to the more seasoned actor we've come to know, each interview has captured the essence of the different stages of his life.
But this one feels different. There’s a sense that he’s stepped into a new phase, one that’s about inner transformation as it is about outward success. He has a daughter now, and with that comes a shift—a deepening, a quiet assurance and a fresh perspective on life that wasn’t there before.
Perhaps it's the 17 years spent in the industry, but the insecurities that once clung to him like shadows in his youth have softened, giving way to self-acceptance. External measures no longer dictate his perception of himself, and he doesn’t seek validation from them either. It takes a certain level of nuanced understanding of oneself and the world to get there, but it makes perfect sense given his favourite film is Wong Kar Wai’s melancholic In The Mood For Love.
This digital cover feels like more than just a feature but a reflection of a man who has embraced his past, matured into his present and is ready to step into the future with newfound clarity. It’s a snapshot in time, one that perhaps, years from now, his daughter will look at and see not just her father, but a man who once grappled with self-doubt, anxiety, and identity, and emerged stronger for it.
ESQUIRE SINGAPORE: You're a father of a newborn. What was your initial reaction when you first held your baby?
DESMOND TAN: At first, I didn’t feel much when I saw her in the labour room—there was so much adrenaline. But once everything settled down, emotions hit me all at once. It was magical. I held her for the first time about six or seven hours after she was born, after all the checks were done. The moment felt surreal; like time stood still. It was just like in the movies, where the camera zooms in from a wide shot of the earth, then to the continent, then to Singapore, and finally into that very room. It was a heartwarming and moving experience, and even now, talking about it gives me goosebumps.
ESQ: How has fatherhood been treating you so far?
DT: I’m loving every moment of it. I haven’t felt frustrated or regretful. Everything’s been smooth, and I feel blessed to have an easy baby. Fatherhood has given me a new perspective on life, made me grow, and changed my priorities for the better. I now focus more on the quality and intrinsic value of things. It’s motivated me to push harder in both life and work, and I believe it’s expanded my emotional range as an actor.
ESQ: What are you currently working on?
DT: I’m working on a production called Devil Behind the Gate, where I play twin brothers. It’s one of the most challenging projects I’ve ever taken on because I have to portray two very different characters with opposite personalities.
Switching from one brother to the other on the same day is challenging, with all the necessary makeup, wardrobe, and character changes. But I enjoy the challenge, even the tough parts because I believe growth comes through deconstruction. This project is helping me build a new foundation for bigger opportunities.
ESQ: You've a daughter; how's it going?
DT: She’s an easy baby—sleeps from 8pm to 8am. But that means I often don’t see her awake. I leave early for work and by the time I get home, she’s asleep. The only time I see her awake is through photos or a baby monitor during my lunch break.
It reminds me of having a Tamagotchi—those virtual pets we had growing up. I turn on my phone, watch her through the camera, and sometimes talk to her through the speaker. At first, she would cry when she heard my voice, but now she recognises it and doesn’t cry anymore. It’s funny when I think about it.
ESQ: What's something you've always dreamt of doing with your child, even before having her?
DT: When I was younger, I imagined having a son to play soccer with, go biking, or camping. But when I had my daughter, everything changed. There are so many things I want to do with her—read books, sing duets, teach her music. The one song I always sing to her is “A Whole New World” and I hope that, one day, we’ll sing it together. It feels like a special bond between us, like the song is our theme.
ESQ: You entered MediaCorp when you were 21. How has the industry changed since then?
DT: The industry has evolved a lot, especially with the rise of streaming platforms. When I first started, people mainly watched TV for entertainment, but now there’s so much competition from productions around the world. We have to adapt to the changing tastes of both local and international audiences.
The way people consume entertainment has changed too—formats have shortened, and social media has become a big part of the industry. I used to see myself strictly as an actor, but now I realize I need to wear multiple hats. Social media helps promote our work, and I’ve come to embrace that.
ESQ: Are you interested in exploring other mediums like international film?
DT: Always. International interactions have opened up new opportunities, and I’m eager to take on international projects. Working on sets with different cultures and experiences always brings out something new in me. It’s exciting, and I’m constantly inspired to grow and explore more. I don’t want to be a wallflower in this industry—I want to leave a legacy, to be a beacon of inspiration for my generation and the next.
ESQ: What is your favourite film of all time?
DT: Definitely In the Mood for Love by Wong Kar Wai. The film captures the beauty of that era in Hong Kong—the costumes, like the iconic cheongsam worn by Maggie Cheung, the silhouette of Tony Leung’s suits, the hair, makeup and music.
I’m particularly drawn to the performances in the film. Tony Leung and Maggie Cheung’s portrayals, the subtlety, and even the silence in the movie speak volumes. The film’s understated emotions hit me more than the loud action of blockbuster movies. For example, the back shot of Maggie Cheung sobbing in the shower is powerful without showing her face. It’s these kinds of cinematic choices that show the power of film.
ESQ: Are you an introvert?
DT: I think I’m a mix, like everyone. We’re all somewhere on that spectrum. Over the years, I’ve become more extroverted, but I still have introverted moments. I get exhausted after being around a lot of people, but I also enjoy sharing things I’m passionate about. I’d say I’m about 80 per cent extroverted, though I’ve never taken the Myers-Briggs test.
ESQ: As a self-proclaimed "Ah Beng," do you ever feel a sense of imposter syndrome at fancy events like fashion week?
DT: I used to think of myself as an "Ah Beng," but I’ve realised I’m more of a heartlander, a local Singapore boy. I often felt out of place at high-society events but over time, I’ve grown comfortable in my own skin. I’ve learned that everyone has doubts, and it’s okay not to know everything. What matters is accepting your weaknesses and being willing to learn and grow, even if it’s just a little each day.
Now, I’m confident in who I am and my background. I don’t see it as imposter syndrome anymore; it’s just part of my journey. I enjoy meeting people at events without feeling the need to prove myself—it's about embracing who you are and owning your story.
ESQ: Do you struggle with small talk?
DT: When I was younger, I did. I felt the need to prove myself, to be recognized, and taken seriously. But as I matured, I realised that doing less is more. When you’re comfortable with yourself, people can sense it, and they’re drawn to you. It’s important to just relax, enjoy life, and share your passions. Over time, I’ve learned that the key is to be comfortable and positive. When you’re relaxed and enjoying yourself, others will want to be around you.
ESQ: When I was doing research for this interview, I came across an interview you had where you talked about how anxiety is one of your biggest fears. Is that true?
DT: My anxiety stemmed from my struggles with language as a child. In this industry, you’re expected to be strong in expressing yourself, which was difficult for me. The pressure of recorded interviews and live shows added to my stress. As a perfectionist, I put extra pressure on myself, which only made things worse.
ESQ: How did you overcome that?
DT: But over the years, I’ve learned to accept who I am—both my strengths and weaknesses. Accepting yourself makes you feel more comfortable and less anxious. You can’t treat anxiety with anxiety, but you can treat it with self-love and love for others.
Being a father has also helped. I’ve read books on parenting that focus on psychology, and I’ve learned that our anxieties as adults often stem from childhood experiences. By revisiting those events, you can unlock and overcome your fears and anxieties.
Photography: Hong Seong Jip
Art Direction: Joan Tai
Styling: Izwan Abdullah
Grooming: Haruka Tazaki
Producer: Oh Seoyul
Photography Assistant: Woo Do Kyun
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