Tyler Hilton: Taylor Swift’s “Teardrops” Crush & Life Updates

Tyler Hilton, known for his role as Drew on Taylor Swift’s 2007 music video for “Teardrops on My Guitar,” recently participated in a viral social media trend highlighting his connection to the pop star, reminding fans of his early work alongside Swift.

Hilton portrayed Swift’s high school crush in the video, a role he secured after the two had become mutual admirers. He recalled being invited onstage to perform “Missing You” with Swift, after which she asked him to appear in her next music video, according to a March 2025 appearance on the “When They Popped Podcast.” “She’s like, ‘I wanted to wait until you were on stage to ask you because I didn’t want you to say no,’ but will you be in my next music video?” Hilton recounted.

Their connection extended beyond the music video set. Hilton shared that he even stayed at the Swift family’s houseboat when he first relocated to Nashville, solidifying a close friendship. The pair reunited publicly in 2018 backstage at Swift’s “Reputation” tour, a moment Hilton commemorated on Instagram, writing, “You killed it bud, great seeing you and the fam, come a long way since Teardrops vid we did!!!”

Hilton, also a musician, has continued to pursue his own musical career, recently touring with Kate Voegele. He has also appeared in several holiday-themed films, including “The Christmas Contract” and “A Christmas Wish,” alongside fellow “One Tree Hill” alum Hilarie Burton.

While Hilton’s professional life remains active, his personal life has undergone recent changes. He and his wife, Megan Park, whom he met on the set of the 2007 film “Charlie Bartlett” and married eight years later, announced their separation in January 2026. The couple share two children.

Hilton has expressed a desire to collaborate with Swift again, recently stating his hope to star in another one of her music videos and even potentially cover one of her songs, according to The Tennessean.