Taylor Swift ‘Cornered’ Actor on Stage and Allowed Him to Live on Her Family’s Nashville Boat

Musician and One Tree Hill guest star Tyler Hilton shares a unique bond with Taylor Swift that began in the mid-2000s. Their connection traces back to Hilton’s admiration for Swift’s debut single, “Tim McGraw,” which led him to mention her in an interview. Swift, then a rising star, took notice and invited Hilton to perform at one of her shows. More recently, Hilton mentioned how Swift once allowed him to live on her family’s boat in Nashville, Tennessee. Here’s how the situation arose.

Musician Tyler Hilton revealed how Taylor Swift ‘cornered’ him before she became hugely successful

Before Taylor Swift’s meteoric rise to fame, she sang country music in local venues. Musician and actor Tyler Hilton told Us Weekly in March 2025 that he knew the pop queen was destined for stardom after hearing her hit single, “Tim McGraw.” When Swift was 15, Hilton told a country music magazine, “‘Oh, by the way, that little thing you did on that new girl Taylor Swift, I’m actually a huge fan of her song. She’s such a good songwriter. … How many 15-year-olds are actually good songwriters?’”

Swift was a huge fan of Hilton’s. “Her manager reached out and was like, ‘Wait, this girl Taylor Swift is actually a huge Tyler fan,'” Hilton recalled to the publication. ‘She’s freaking out that you mentioned her in this magazine.’ And I was like, ‘Oh, that’s so adorable.'”

Later, Swift’s manager invited Hilton to see Swift perform at a country bar in South Carolina. According to Hilton, the teen “cornered” him onstage and asked him to be in her music video. He agreed and starred in the video for “Teardrops On My Guitar.”

While Swift benefited from her blossoming friendship with Hilton, he also received help from 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 told Us Weekly. “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.”

Tyler Hilton posted a series of selfies with Taylor Swift in 2018

Tyler Hilton is a true fan of Taylor Swift. In 2018, he congratulated her on her successful “Reputation” tour with a series of selfies on Instagram.

“Congrats to @taylorswift @camila_cabello @charli_xcx on a killer last night of Tour!!” he captioned the post, which included several photos of him and Swift posing for their phone camera. “You killed it bud, great seeing you and the fam, come a long way since Teardrops vid we did!!!”

In October 2018, Hilton recalled the houseboat tale he still talks about in 2025.

“My dad came out to Nashville, and we were looking for a place for me to stay, and Taylor and her family were like, ‘You can just stay on our boat! We have a boat near our house, and it’s like a house, so just stay there,’” Hilton told Entertainment Tonight. “Just the sweetest family, the sweetest girl, and one of the most talented people I’ve ever met.”

Did the 2 stars ever date?

Taylor Swift had Tyler Hilton play her unrequited crush in the music video for “Teardrops On My Guitar.” So, did they ever date?

Swift and Hilton have only ever been close friends. Hilton married Megan Park in 2015, and Swift is very serious with Travis Kelce.

Hilton once hinted that he’d be open to remaking the music video he once starred in. “And maybe we’ll remake the old ‘Teardrops’ video for old time’s sake,” he told Elite Daily.

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