20 Years Ago, She Met an Aspiring Musician on the Beach! Now She’s a Global Pop Icon

Holly Armstrong, a fan of Taylor Swift for over $20$ years, has met the star twice — once in 2003 and again in 2019.

Holly Armstrong became one of Taylor Swift’s first fans when she saw the star perform on a boardwalk in New Jersey in 2003. The $34$-year-old Swiftie tells PEOPLE that the pop superstar’s music — and the fandom around it — has been a “lifeline” for her. Armstrong has recently taken her fandom to the next level, launching an online shop full of handmade crafts loosely inspired by some of her favorite lyrics from Swift.

As Holly Armstrong recounts the experience of receiving a DM from Taylor Nation — pop superstar Taylor Swift’s official fan club — inviting her to a secret listening session ahead of the release of Swift’s seventh studio album Lover in 2019, she doesn’t hold back.

“I lost my s—,” Armstrong, a 34-year-old Texan, tells PEOPLE.

The listening party, dubbed in the fandom “Secret Sessions,” was a “fever dream” and everything Armstrong could ask for: it was “cathartic” to be surrounded by so many other superfans, she says, who could scream and cry together as they listened to an album of brand new songs that would soon soundtrack their lives.

But the fan meet-and-greet with Swift that followed was something else entirely. For many Secret Sessions attendees, the chance to chat and snap a photo with the “Cruel Summer” singer is a once-in-a-lifetime opportunity — but Armstrong had already met Swift over a decade prior.

In 2003, years before the iconic singer-songwriter would release an innumerable string of chart-topping hits or collect her 14 Grammy awards, Swift, then a young teenager with a guitar and a dream to make it big in country music, was performing a small acoustic set on the boardwalk in Point Pleasant, N.J.

Armstrong, who was $12$ at the time, was on vacation with her family and spotted the young musician.

“There were probably 20, 30 people at most, just gathered around,” she remembers. “It wasn’t a moment I thought would be as important as it has become.”

After Swift finished her set, she handed out demo CDs to audience members — and when Armstrong went up to meet her, Swift asked if she wanted her to sign it. “We very briefly talked about whatever $13$-year-old girls talk about,” says Armstrong. “I was just over the moon.”

Though the CD only had two of Swift’s songs — demos of unreleased tracks “Lucky You” and “Smoky Black Nights” — when Armstrong returned home to Texas, the tunes played in her Walkman on repeat.

“A few months after I got home from the beach, I went through something no kid should ever really have to go through,” she says of a life-altering event from her childhood. “And in that trauma, in that fear, in that feeling of not feeling safe, I latched onto the closest thing that I could — and that was Taylor’s music.”

For several years, Armstrong’s love of Swift’s music was entirely personal. But slowly, as Swift put out her debut album in $2006$ and released her first chart-topping record in $2008$, the “gem that I had kept to myself for so long,” says Armstrong, became one of the most famous singers on the planet.

As Swift’s popularity grew, so did her community of fans, who flocked to social media platforms like MySpace, Tumblr, Twitter and Instagram to discuss the pop sensation, debate their favorite songs and theorize about her future releases. But even as one of her earliest supporters, Armstrong says, she stayed quiet in the fandom about her experience of meeting Swift back in 2003 — wanting to protect the memory that had become so sacred for her.

“The only social media I really did was Instagram, and I maybe had $100$ followers — just family and friends,” says Armstrong. Though she would post her 2003 photo with Swift on the anniversary of the New Jersey concert every year, she never intended for it to reach the wider Swiftie community.

But the day Swift released “ME!” — the lead single from Lover — in 2019, Armstrong obsessed over Easter eggs in the music video, pulling out all of her Swift memorabilia from over the years and laying it out on her bed alongside the signed demo CD. She recorded a video of the moment, uploaded it to her personal Instagram account, and the post took off.

“I don’t know what I did, I don’t know what hashtag I used, but it got swept up in the Swiftie community,” recalls Armstrong. “I was so flattered.”

And when more fans discovered the 2003 photo of Armstrong with Swift, her account received even more attention and “an outpouring of kindness unlike anything I’d ever imagined,” she says.

As she became more enmeshed in the fandom over the next few months, she discovered how the community acted as a “lifeline for so many people, myself included,” Armstrong tells PEOPLE.

For instance, when fans who are struggling to pay their bills try to sell their merch to make some extra cash, rather than buying the merch, fans will donate a few dollars to help out so that Swifties in need don’t have to part with their prized possessions. And when Armstrong candidly opened up about a traumatic moment from her childhood on social media, she was overwhelmed by the response.

“The way people responded to that — I have no words,” she says.

Armstrong even credits the fan community for uplifting her story across social media in 2019, so much so that it caught the attention of Swift herself, who invited Armstrong to a Secret Sessions in August before Lover dropped.

When she finally reunited with her idol after 16 years, they had a lot to chat about — Swift even remembered performing on the New Jersey boardwalk, says Armstrong.

“And to top it all off, she thanked me,” Armstrong adds. “It was the most validating thing I’ve ever heard, and I didn’t know I needed to hear it.”

When Armstrong returned home from the listening party, no longer sworn to secrecy and able to share her experience on her social media platforms, fans similarly showed up, sending her dozens of messages, excited that she finally got the chance to reunite with Swift.

And Swifties have continued to support Armstrong over the past few years.

During the pandemic, a bout of extreme burnout from her corporate job sent her into a deep depression and prompted her to need six months of leave. With her time off, she discovered a love of crafting — painting, designing jewelry and making candles — and eventually decided it was time for a career shakeup.

Armstrong left her job and started working on Starlight & Sage Co., an online shop where she sells hand-crafted goodies loosely inspired by some of her favorite lyrics and themes from Swift’s music, which officially launched on July 23. She says she’s been amazed by the level of interest from fellow Swifties across social media.

On the first day of operations, she received 22 orders — even though she says she “genuinely did not expect any.”

“It’s been the most fun I’ve ever had,” says Armstrong of the new business. “Swifties show up.”