From Tyler Hilton’s “Teardrops on My Guitar”
Tyler Hilton played Drew, Taylor’s high school crush, in one of her first music videos in 2007.
As for how he got the gig, the actor noted that the two are fans of each other – he loved her song “Tim McGraw” and she had seen him on One Tree Hill – and invited him on stage to perform “Missing You.”
“She said, ‘I wanted you to listen to me until I got on stage because I didn’t want you to say no,'” Tyler recalled on a March 2025 episode of his podcast When They Popped. “She said, ‘But will you be in the next music video?'”
The two became close, even staying on Swift’s houseboat when he first moved to Nashville. Then, in 2018, Taylor and Tyler reunited backstage on the Reputation Tour.
“You did it,” the Walk the Line alum wrote on Instagram, adding, “So happy to see you and your family, we’ve come a long way since the Teardrops video!!!”
Things didn’t work out for Taylor and Drew, but Tyler found love with Megan Park. The couple met on the set of Charlie Bartlett in 2007 and married eight years later. However, the couple, who had two children together, announced their divorce in January 2026.
Tyler, who is also a musician, has recently toured with Kate Fogel and appeared in both A Christmas Contract and A Christmas Wishes with One Tree Hill alum Hilarie Burton.
