Regina Song on finding love again: “It’s hard to find someone who can handle me”

Local sensation Regina Song, the 21-year-old singer behind hits like The Cutest Pair (racking up 44 million streams!), is back with Love Me Again, a raw, emotionally charged follow-up to her single Fairy. While Fairy simmered with quiet anguish, Love Me Again lets it all out, diving deep into the messy aftermath of first love.

With over a million monthly listeners and a sold-out Southeast Asia tour under her belt, Song continues to solidify her status as a global artist, even gracing stages like Wanderland Festival and the upcoming LaLaLa Fest alongside international bigwigs. 

We delve deeper into the story behind Love Me Again, why the singer's healed heart will be ready to drench her next love with an intensity born from lessons learned and a renewed capacity for deep affection in this interview with Regina Song.

I understand that your mum sent you for piano lessons but when did you first realise you liked singing better?

Oh, that's a really good question. I think I've always been really interested in pop music. I grew up listening to a lot of female pop singers like Taylor Swift, Selena Gomez, Apple Levine and Katy Perry. So I always had this really strong interest in popular music. I liked Taylor Swift the most because of the way she tells her stories and the way it's also personal. I realised that singing is really fun.

Were there a lot of musical influences in your family? 

Like a lot of Singaporean families, we listen to Mandopop a lot. They love Jay Chou; I listened to a lot of that era’s music. My mum was also classically trained on the piano, which is why she sent me for piano lessons. And my dad learned the guitar, and he was in the Chinese orchestra, so there are quite a lot of similarities. I basically picked up a lot of instruments that my parents picked up.

When exactly did you realise you wanted to make music your career?

I think I realised that I wanted to make music my career when I started writing music? Like, there was always this thought at the back of my head that I wanted to write songs. I wanted to be a songwriter and even if I wasn't a performer, I knew I wanted to actively be writing songs and putting my work out into the world. 

When I was 17, I had this very strong urge to put out a song during the June holidays. That was the very first time I had ever experienced releasing a song, producing the song, making a marketing plan and trying to promote my song. So I think I went into it really blindly, honestly. But the entire experience made me realised that this is really what I want to do. Because when I hear my friends tell me, like, ‘Oh my God, I really like your song, it really helped me process my feelings and I really enjoy listening to it,’ it does something to me. I feel like I've actively contributed to someone's life, especially if it's my friend. It just filled me up with so much meaning and so much fulfillment. That was when I realised I really wanted to keep putting out songs and become an artist.

So going back to that age at 17, how did you put out your first work?

It was released online; it was my first single called Lucas. And I worked with a few friends of mine. They were very kind, too. I was supposed to learn how to do production. And then the producer, in the end, he asked me, ‘Oh, do you write songs?’ To which I replied, ‘Yeah, actually, I write songs.’ And I showed him my songs, and he liked them. And we were like, ‘Okay, let's work on the song together.’ So that's how it happened.

Did your studies help you with songwriting or any form of musical skills?

So when I went to School of The Arts, Singapore (SOTA) and I did classical piano. We had a lot of hands-on lessons, like, going to ensembles and learning about history, theory, rhythms and all of that. But I don't think there was an avenue to learn about songwriting or production, because that was very much like a school for classical music. I would say the people around me really helped me — like the environment — because I had a lot of friends who were interested in pop music. We played pop music all the time. I have friends who are also songwriters, and it just feels a little bit less alone when you're writing songs with people.

My other friend, her name is Rain; she's also a singer-songwriter from Singapore, and her artist name is Rhyu. She was one of my best friends growing up, and we wrote a lot of songs together. So I would say in that environment, it really shaped the way I looked at music and how I wrote my music. 

I joined an acapella group, Syncopella, for six years and I really developed a fondness for choir, like layering vocals and creating interesting harmonic progressions for my vocals. So that's very evident in a lot of my music. I was also in a pop band, and it really trained me to develop my presence as a singer because when you're a singer in a band, you're not just performing by yourself. You have to work with other people and figure out how they can best support you. So being in SOTA really did shape me very well. I'm really grateful for the opportunity to be in an art school where everyone is amazingly talented and inspires me a lot. 

I think it's great having a team supporting you and feeling less alone. I think when you're doing music, there's a lot of fear and confusion of not really knowing what's going on. So being in a label helped guide me to have a clearer vision of what I want and also I don’t have to do everything by myself. I think that's very important, because everyone has their strengths and weaknesses. As an artist, I got to play to my strengths and not worry about so many things. 

How do you define success?

I think success is how the person wants to define it. For me, personally, I define success as being dedicated to one's craft and fully, truly showing the best side of themselves and being true to their artistry. I strongly believe that not all music is meant to be played on a radio or blown up. I genuinely believe that if someone were to stay true to themselves, that is being very successful, because it's very easy to be distracted and feel like you're not good enough because you didn’t make something that's mainstream. I think it was a really long discovery process for me. I had to find the balance between putting out something that I liked and putting out something that I know other people like, as well. So I think that's another definition of success. I would say, trying to find a good balance, like the yin yang of trying to make music and putting out your artistry. 

Do you feel any pressure to live up to the expectations of your prior success?

Well, I definitely feel it because I do have quite a competitive nature, and I'm especially competitive towards myself. I like to set a higher standard than what I did before; make music that I feel would better represent me. I definitely feel the stress because it's not easy trying when you are a quote-unquote pop girl and you have to find ways to reinvent yourself all the time. I think this is especially the case for women; we just have to find new shiny facets of ourselves all the time, like what Taylor Swift said. I truly resonate with that, because it's really hard. With that said, I'm really excited to just develop my sophomore album and put out work that really resonates with me. Like I said, I don't believe that all music was meant to blow up or become a radio hit. 

What were some of the sacrifices you had to make in order to be where you are today?

Let me think (pauses) I wouldn't say I sacrificed studying, but I made sure to take a gap year to really focus on learning about myself and doing music. I did have to sacrifice some sleep. I'm not sure if this would be considered a sacrifice, but I think being singer-songwriter and understanding how artists have completely changed the game of music. Last time, it was very label-driven and if you don't have the resources, it's going to be hard for you to blow up. But now, with social media, working the TikTok algorithm and having reels and short form content in place, there's so much more possibilities and potential for a small artist to get recognised. I think because of that, I have spent a lot of time on social media, and it has taken some kind of toll on mental health. Some days will be bad. Some days you'll be like, ‘You know what? That's not that bad.’

I did have to spend a lot of time affirming myself and all. So sometimes my mental health takes a hit. Yes, I'm not gonna lie.

Another personal sacrifice would be to not be in a relationship. Actually, in the one and a half years that I was in the label, I was also in a relationship. At that time, I was seeing someone and I thought that the person was great. I just don't think that I was diverting my energy into the right places, which is why I felt like I had to focus on my career. 

How do you manage your mental health? Do you talk to somebody about it?

Honestly, I like to give myself motivational talks. I don't really enjoy talking to other people about it, because I just feel like it's a very me thing. It's very much like an internal thing. So if I ever get demoralised, I'll just be like, ‘You know what? Yes, it matters, but it shouldn't be something to affect my mood so much.’ That’s the best way that I can cope with it and of course, I'm always trying to brainstorm on how I can continue to engage with my audience.

I guess you're your own personal hype woman in that sense. 

Yeah, we all need to hype ourselves as well. 

What do your family and friends think of your success today? 

I would say that my parents have been relatively supportive; I'm glad that they are proud of me. My mum has been quite involved in my life; I would say she likes to give her input anytime she can, which can be a little bit frustrating sometimes, but I know she's just trying to be a good mum. My dad is very much like a digital marketer, so he likes to ask me, ‘Oh, do you need me to write an ad for you?’ It’s not a very big scale, but their effort and their intention makes me very touched. Sometimes I do feel like all the successes that have happened were supposed to happen anyway, because I was quite desperate to try to prove to them that I could do it. 

Was there any point where you had a cut-off time if this doesn’t work out? 

If this doesn't happen, I think they will probably expect me to continue my studies, or anything like that. I think my brain works in a really unique way where I'm like, ‘Okay, I desperately wanted them to know that I didn't feel like I needed to go to school.’ I mean, I do believe in a good education, but I just feel like it wasn't time. So in the end, I did enroll in school, and I enjoyed it, but I felt like it was really distracting me from what I really wanted to do, which is to really spend time doing my music and building my career. 

I felt like school was draining my energy quite a bit, because I had to go to school every day and learn about music, but even that was a lot, and I just kept thinking, I needed to do something about that. I'm just happy that people like my music. It's still a surreal feeling.

Let’s talk about your new song, Love Me Again. Is it a sequel to The Cutest Pair?

The Cutest Pair was definitely a song that was heavily inspired by the relationship I had. It seems like a happy song, sonically, but if you really read the lyrics, it's actually coming from a place of not being enough. A lot of things happened after my relationship ended, and it was really hard for me, because that person was my first love, and I really invested a lot into the relationship.

My singles Fairy and Love Me Again are closely tied together because they were written about the same period. Basically, my first love found someone new, which is very normal but it doesn't mean that it didn't hurt. I was definitely really affected during that time, because it happened during the peak of everything. 

I had started to gain a lot of listeners, a lot of traction, but while it was the best period of my life, it was also the worst period of my life. I don't know why I just felt this way. Fairy was about me being angry, but ‘love me again.’ It was me going through the grief— the loss of someone. I think that I was very focused on being angry, because all of my friends were like, ‘Oh my God, forget him.’ And I was like, ‘Yeah, forget him.’ But I didn't give myself time to process and just be sad about it. So Love Me Again was kind of me processing everything.

It’s the grieving process. I guess you encapsulated your emotions in those songs too. 

It came together because when I started writing the verse, I remember it being the festive season and I was not feeling it. I was getting Christmas blues and I was not feeling happy at all. It just happened that the person had changed his profile picture and he hasn’t done it in so long, which was crazy! The picture showed the location where we were last together and now he’s there with someone new. It really got a reaction out of me. So I went to the piano and I started writing the first verse. Everything came together within one or two days. I really like to write songs when I feel intense about something. 

At your age right now, coupled with this public persona, is it harder to make friends or even date?

When people are genuine towards me, I feel like I can feel it. That, I’m not concerned about. I guess it’s hard to find someone who can handle me. I think I can be quite a handful sometimes. It’s not been easy, but I wouldn’t say it’s been impossible. I have definitely met a lot of people who have inspired me a lot, who really understand me. 

Say, you find yourself in a new relationship. What kind of a girlfriend do you think you would be?

I think people can be afraid to approach me just because I have gained some kind of popularity and that’s not easy to handle. So that’s what I meant about being handful, because they have to answer a lot of questions. I am just trying to find someone who really understands me and likes me for me, and not because of any other reason. I would be an extremely affectionate one. I give love in all ways. You know the love languages? I would give all five because I am quite intense when it comes to being in a relationship and dating someone. I always like to be emotionally available to whoever I am seeing. If I am in a relationship, my heart and soul will be put into it.

Do you believe this all ties back to your star sign? If you believe in astrology.

I do believe in astrology. I am Aquarius and it just happens that I (pauses) it’s weird; I’ve always been talking to and dating just Aquarius men. It’s a really interesting thing. I don’t know what it is about Aquarius, about being in love, but I remember they don’t like their freedom being taken away, which is quite true. I don’t like to be controlled. As long as the other person can understand, that’s great.

You played in Wonderland in March and you have another upcoming festival this year, which is LaLaLaFest. There have been big public performances for you, so what’s your preparation like?

I’m extremely excited because the experience at Wonderland was so surreal. Playing at a festival and having people watch you is not something I get to experience every day. I took in everything, all the moments. I was really taken care of in the Philippines and I had a wonderful time playing my set. The most important thing about playing in a set is thinking about what actions you want to do and try to give every performance something special. I’m trying to think about what outfits to wear, what unreleased songs to play and giving people a sneak peek. I’m really excited to be in Indonesia because I love being in Indonesia. The last time I went on tour, the fans there were amazing and I can’t wait to play alongside many amazing artists that I look up to. It’s a great honour and I am really excited.

What’s your personal style like?

I like to wear girly things: I like frills, I like to wear pink and colours that make me stand out on stage. I like something flowy and things that make me look tall on stage because I’m not that tall; I’m only 160 cm so I want to make sure I dress in a way that I look tall. 

Are we going to expect a new album this year?

Yes, it’s going to be released early next year. I haven’t announced anything yet but it’s going to be my sophomore album and I’m going to announce the title when I have the concept and everything else settled and sorted out. It’s going to have 11 to 13 tracks and I am going to have a deluxe album as well and that’s going to be very exciting as I’ve never had a deluxe album before. It’s going to have two to three more songs and I am leaving my personal favourites in there. 

This album is written about my first relationship (pauses) Fangirl was a lot about my teenage experiences, being very naive and new to love. But I want to show a new, more mature side to myself having been in one relationship; I want to show how it started and how it ended, and showcase the different stages of being in a relationship. The album is inspired by a lot of nature references in my songs and it’s going to be a whole new concept and I am really excited about it. Even before Fangirl was released, I was already thinking about this album.

Share with us one motto you’ve been living by lately.

Mine would be, if you can choose to be happy, choose to be happy. Life can be a lot and it’s easy to dwell on the bad things but I like to keep a positive outlook on life.

Love Me Again by Regina Song is available on various streaming platforms