20 Years Ago, She Met a Budding Musician at the Beach. She’d End Up Becoming One of the Biggest Pop Stars in the World 

When Holly Armstrong got a DM from Taylor Nation — the official fan club of Taylor Swift — inviting her to a private listening session for Swift’s seventh studio album Lover in 2019, she was floored.

“I lost my s—,” says Armstrong, a 34-year-old from Texas, speaking with PEOPLE.

These intimate events, dubbed “Secret Sessions” by fans, were a surreal dream for her. Sharing the room with fellow Swifties, screaming, crying, and soaking in brand-new songs before the world heard them — it was, in her words, “cathartic.”

But what came after the music meant even more. Fans at these sessions get a rare opportunity to meet Swift in person — and for Armstrong, it wasn’t the first time.

Back in 2003, long before Taylor Swift became a global icon, she was just a teenager with a guitar playing an acoustic set on the boardwalk in Point Pleasant, New Jersey. Armstrong, then 12, was on a family vacation when she happened to spot the young performer.

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

After her set, Swift handed out demo CDs. When Armstrong went up to meet her, Swift offered to sign it. “We very briefly talked about whatever 13-year-old girls talk about,” she says. “I was just over the moon.”

The CD featured two unreleased songs — “Lucky You” and “Smoky Black Nights” — and Armstrong listened to them endlessly on her Walkman back home in Texas.

Soon after, Armstrong experienced a traumatic event that would shape her childhood. “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,” she says.

For years, her love of Swift’s songs was something private. But as Swift’s fame exploded with her debut album in 2006 and her first chart-topping record in 2008, Armstrong watched the artist she once met on a boardwalk become a global superstar.

Still, she kept her early encounter mostly to herself. “The only social media I really did was Instagram, and I maybe had 100 followers — just family and friends,” Armstrong explains. She’d post the 2003 photo of her and Swift every year on the concert anniversary, never expecting wider attention.

That changed in 2019. When Swift dropped “ME!,” the lead single from Lover, Armstrong dove into the video’s Easter eggs, digging out all her memorabilia — including the signed demo CD — and sharing it in a video on her personal Instagram.

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

As fans discovered the old photo, Armstrong’s post went viral, and she received what she describes as “an outpouring of kindness unlike anything I’d ever imagined.”

Immersing herself in the fan community, she found more than just people to talk music with. “The community is a lifeline for so many people, myself included,” she tells PEOPLE.

She shared a deeply personal childhood trauma on social media, and the fanbase responded with overwhelming support. “The way people responded to that — I have no words,” she says.

That same year, Swift herself took notice. Armstrong was invited to the August Secret Sessions for Lover.

Reuniting with Swift after 16 years was surreal. They talked, and according to Armstrong, Swift remembered performing on that New Jersey boardwalk.

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

Once she was free to share the experience online, fans flooded her inbox with messages, thrilled to see her story come full circle.

Over the years, that community hasn’t left her side.

During the pandemic, Armstrong hit a low point, burned out from her corporate job and battling depression. She took a six-month break — and discovered a love for crafting. She began painting, making candles, and designing jewelry. Eventually, she decided to turn her passion into something more.

She launched Starlight & Sage Co., an online shop selling handcrafted pieces inspired by Swift’s lyrics and themes. The store officially opened on July 23 — and Swifties showed up.

On day one, she received 22 orders.

“I genuinely did not expect any,” Armstrong says. “It’s been the most fun I’ve ever had. Swifties show up.”