Taylor Swift was a determined teenager when she approached Tyler Hilton, now 41, and asked him to be in the Teardrops On My Guitar music video with her.

The Bejeweled singer, 35, was just 15-years-old at the time, and Hilton was a touring musician who was guest starring on One Tree Hill. 

Hilton talked about how much he liked Taylor’s song with Tim McGraw in an interview back in 2007 saying that while he admired her songwriting and moxie, he had no premonition that she’d become the global superstar she is today. 

‘I didn’t know this, but she had watched all my videos on YouTube, like, all these little skits I did,’ he said.

‘Her manager reached out and was like, “Wait, this girl Taylor Swift is actually a huge Tyler fan. She’s freaking out that you mentioned her in this magazine.”

‘And I was like, “Oh, that’s so adorable,”’ Hilton continued, explaining that Swift’s manager invited him to her show at a little country bar in Southern California.

Taylor Swift was a bold and determined teenager when she approached Tyler Hilton, now 41, and asked him to be in the Teardrops on my Guitar music video with her

The Bejeweled singer, 35, was just 15-years-old at the time, and Hilton was a touring musician who was guest starring on One Tree Hill at the time

Hilton went to that show, where a young Swift performed his song Missing You and asked him to perform with her.

‘[She was] a very forward 15-year-old,’ he told Us Weekly. 

‘She literally corners me on stage and goes, “I didn’t want to ask you backstage ’cause I was afraid you’d say no, but would you be in my next music video?” 

‘That’s how I ended up in the Teardrops On My Guitar music video. And after that she was like, “Oh, I’m doing some shows, would you want to come open for me?” 

‘And she just kept getting bigger and bigger,’ he said. 

Hilton explained that the they stayed in touch and he watched her get more and more famous.  

‘I was just charmed by her and her family. We became close and then when I moved to Nashville, they let me live on their boat and live with them for a little while when I first moved to Nashville,’ he recalled. 

Hilton lived on the Swifts’ boat for a few weeks while he looked for an apartment in Nashville.  

Hilton talked about how much he liked Taylor’s song Tim McGraw in an interview back in 2007 saying that he admired her songwriting and moxie. Seen here in 2006 

‘I didn’t know this, but she had watched all my videos on YouTube, like, all these little skits I did.’ Seen here in 2008

‘Her manager reached out and was like, “Wait, this girl Taylor Swift is actually a huge Tyler fan. She’s freaking out that you mentioned her in this magazine.”‘ Seen here in 2019

‘And I was like, “Oh, that’s so adorable,”’ Hilton continued, explaining that Swift’s manager invited him to her show at a little country bar in Southern California.’ Seen here in 2025

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‘They were just, like, the Swifts — like, my buds — and their little teenage daughter was a fan. And I was like, “Aw, that’s so sweet.” And now she’s the biggest star in the world, he said.

He also shared that Taylor would play him her new song straight from the lyrics she wrote in her diary. 

‘She was playing me songs in her bedroom out of her diary for her second record,’ he told the outlet. 

‘She was playing me White Horse and it was crazy because I’m in her bedroom and I’m like, “Whoa, this girl is actually, like, princess, fairy, unicorn girl.” 

‘It’s not an act — she actually had her songs written in, like, a fluffy diary and she is that nerd, you know what I mean? 

‘That’s what’s so sweet about her and I think is responsible for her longevity — it’s not an act. She’s actually that much of a nerd and it’s so endearing,’ he shared. 

Hilton admitted he ‘actually can’t believe she became as famous’ as she did.

‘We all collectively thought she was so adorable. It is like when the nerdy girl in high school becomes famous, she is that earnest,’ he said. 

‘She’s like, “Do you wanna hear another song outta my diary?” I’m like, “Oh, OK.” And they were all really good, but it was just like, “This is so funny.”’

Since that time, Taylor has released has 11 studio albums and won 14 Grammy Awards.

She’s also put on several global tours including her recently completed, record-breaking Eras Tour.