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.
As for how he got the gig, the actor noted the two were fans of each other—he loved her song “Tim McGraw” and she watched him on One Tree Hill—then invited him on stage to perform “Missing You.”
“She’s like, ‘I wanted to wait until you were on stage to ask you because I didn’t want you to say no,'” Tyler recalled on a March 2025 episode of the When They Popped Podcast, “‘but will you be in my next music video?'”
The two became close, with him even staying on the Swift family’s houseboat when he first moved to Nashville. Then in 2018, Taylor and Tyler reunited backstage at her Reputation tour.
“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!!!”
While it didn’t work out for Taylor and Drew, Tyler found love with Megan Park. The two met on the set of 2007’s Charlie Bartlett, and wed eight years later. Though the pair, who share two children, announced their split in January 2026.
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.
