Skip to main content



Gen Y Speaks: I’ve bent right to your wind, Taylor Swift. I've been (too) enchanted by your personal life

I still remember the first time I heard a Taylor Swift song during a long bus ride — I was 20 and was sharing earphones with my best friend on her iPod.

Gen Y Speaks: I’ve bent right to your wind, Taylor Swift. I've been (too) enchanted by your personal life
Follow us on TikTok and Instagram, and join our Telegram channel for the latest updates.

I still remember the first time I heard a Taylor Swift song during a long bus ride — I was 20 and was sharing earphones with my best friend on her iPod.

She had recently discovered and fallen in love with the singer and her songs, one of which was a tune about a girl who had teardrops on her guitar because of an unrequited love named Drew. 

One might think that since I am the same age as Swift (we are both born in 1989), I’d understand a song that Swift wrote as a 17-year-old teenage girl for her debut album at the time.

But my first impressions listening to Swift’s song on that bus was that it sounded like an angsty teen whining about her love life.

And so, I judged my friend’s taste in music negatively, though I now think that I was being rather mean at the time. I also wondered if there was something going on in her love life that I did not know about. 

I took notice of her later albums (Red was my favourite) and spent my early 20s listening to her various heartbreaks and exploits.

Eventually, I lost interest in her music at some point and have never been to any of her concerts when she came to Singapore, namely the Red Tour in 2014 and the 1989 World Tour in the following year. 

But at the height of the pandemic in 2020, Swift collaborated with two of my other favourite artists — Bon Iver and The National. The moody, dreamy vibes of The Long Pond Studio Sessions, a documentary about her album Folklore which featured both artists, really resonated with me at that time. 

After that, I was hooked again. Tay Tay was cool again, in my books.


Even though my music tastes have evolved over the years, I have found her verses mostly on-point.

The confessional, heartfelt nature of her lyrics has always made listening to her songs feel like reading her diary. 

Like her eager fans and self-styled detectives, I remember scrutinising the easter eggs she would drop in her lyrics and music videos for clues about her personal life. 

And even when I stopped listening to her music, my fascination with her private life continued. 

Because I follow her on social media, , I know she has three cute cats — Meredith Grey, Olivia Benson and Benjamin Button — who regularly appear on her Instagram feed. She is close to her mom, who is battling cancer.   

I guess it is also inevitable for Swifties to be overly invested in her love life, and I admittedly am guilty for this too. 

I stopped being a fan of John Mayer (the most-likely villain in her song Dear John), thought Harry Styles (did he inspire the track Style?) was cool, and was confused about her fling with Tom Hiddleston.

Then, I betrayed her by siding with the Kardashians during the infamous phone call in 2016.

Actor Jake Gyllenhall, who dated Swift for three months in 2009 when she was 20 and he was 29, was arguably the protagonist in the fan favourite song All Too Well. He is still a subject of heated debate among her fans. 

In recent months, her whirlwind relationship with Matt Healy of rock band 1975 was in the spotlight because of his past misogynist comments during a podcast surfaced. Many fans expressed their disappointment. They have reportedly split ways.

Explaining the infamous spat between Kanye West and Taylor Swift would require diagrams and timelines, but it is not difficult for any fan to recount, though I won’t attempt to tackle it here.

The point is: Many of her fans would fight to their death for her as if they knew her personally.

I’m almost embarrassed to admit I know all these details about a celebrity. I fell so deep into the rabbit hole, even though ironically, the friend who introduced me to Taylor Swift is no longer a fan.


At this point, readers who are non-Taylor Swift fans must be rolling their eyes at yet another public declaration of love for the star, amid all the news about Swift’s Singapore concerts.

But I decided to pen this piece because I saw some confusion over why she is such a cultural phenomenon, and why my fellow Swifties were so feverish in their pursuit of concert tickets.

Full disclosure: I tried for a seat at the Eras Tour. My queue number was over 470,000 for the UOB pre-sale and 981,181 for the general sales.

I eventually got tickets from a much more resourceful fan who rallied eight family members and friends to book tickets during the pre-sale.

But even if I had not, I don’t think I would be shedding any tears.

There are many reasons for the overwhelming response despite a whopping six shows available, and the rest of Southeast Asia were eyeing those tickets too. After all, she hasn’t performed here in eight years. 

Still, the overnight, snaking lines at some SingPost outlets for the tickets and the emotional outbursts of some fans through the traumatic (in their own words) ticket-buying process drew some judgement.

Speaking in defence of the fans, I understand how some fans might feel death by a thousand cuts when they realised they would not be able to watch her perform live with other fans. 

A part of me thinks this parasocial behaviour is weird. 

Taylor Swift reminds me of a friend who has an interesting, messy life. Just that instead of listening to a long, meandering rant, I am rapt as she croons about how ‘’casually cruel in the name of being honest’’ an ex was.

In Antihero, a song from her latest album midnights, Swift reflects on being older but never wiser. This level of self-awareness is admirable because it is rare, and stuck with me as I’m approaching my mid-30s. 

Except of course, how could most people possibly relate to her? She was revealed to be the celebrity whose private jet emitted the most carbon dioxide in 2022. 

She is currently worth an estimated US$740 million (S$998 million) — with her revenue mostly coming from record sales and concerts — and is expected to become a billionaire by the end of her Eras Tour, according to Forbes. 

Her relationships are not always the only aspect of her life under judgement. 

Her activism has been accused of being calculated and performative: she was criticised for not speaking out more during the Trump years and was previously accused of using LGBT rights as a fashion statement in her catchy jingle “You need to calm down”.

In a way, I sympathise with her.

Despite gender equality at its golden age, women are often still held to different standards — Taylor Swift has sung about how she has been judged for ‘’playing the field’’ because of her dating history, but a man would be considered a ‘’boss’’ or ‘’alpha type’’ for the same thing.

That is just the reality that we live in.

I think Miss Americana, in her never-ending quest to be relatable and likeable, has over-delivered. 

After all, many of her fans have inevitably fallen willingly into her charms, myself included.

She is one of the most heavily scrutinised women in the world, and in all this chaos, she makes the best out of it with her sad, beautiful, tragic hooks.

I think Swift is just another singer with a complicated, albeit highly marketable, personal life.

But she is also a savvy storyteller, and I respect that despite all the drama, she is still captivating younger audiences today. 


Linette Heng, 33, is a freelance writer.


Related topics

Taylor Swift The Eras Tour music

Read more of the latest in



Stay in the know. Anytime. Anywhere.

Subscribe to get daily news updates, insights and must reads delivered straight to your inbox.

By clicking subscribe, I agree for my personal data to be used to send me TODAY newsletters, promotional offers and for research and analysis.