Key Highlights

Tyler Hilton From “Teardrops on My Guitar”

Tyler Hilton portrayed Taylor’s high school crush Drew in one of her first music videos back in 2007.

Connection: The actor noted that both he and Taylor were fans of each other—he loved her song “Tim McGraw,” and she watched him on One Tree Hill. This led to her inviting him on stage to perform “Missing You.”

Invitation: Tyler recalled on a March 2025 episode of 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?'”

Friendship: The two became close, with him even staying on the Swift family’s houseboat when he first moved to Nashville. In 2018, Taylor and Tyler reunited backstage at her Reputation tour.

Instagram Post: “You killed it bud,” the Walk the Line alum wrote on Instagram, “great seeing you and the fam, come a long way since Teardrops vid we did!!!”

Love Story: While it didn’t work out for Taylor and Drew, Tyler found love with Megan Park. They met on the set of 2007’s Charlie Bartlett, and wed eight years later. However, the couple, who share two children, announced their split in January 2026.

Current Projects: Recently, Tyler, also a musician, has been touring with Kate Voegele and has starred in both The Christmas Contract and A Christmas Wish with fellow One Tree Hill alum Hilarie Burton.