To date Taylor Swift is to essentially guarantee that you will be immortalized in one of her albums. From her first high-profile boyfriend at 18, the singer has relied on a never-ending string of romantic relationships to inform her songwriting. Check out our timeline of Taylor Swift’s unique and extensive dating history that matches her exes to her hit songs.
Taylor dated Joe Jonas in the summer of 2008, but things were over by fall. Still, the relationship remains infamous because of its cruel and cold end. In a November 2008 appearance on Ellen, Taylor explained, “When I find that person that is right for me he’ll be wonderful. And when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18.”
Taylor went on to write three songs about Jonas: “Last Kiss”, “Better Than Revenge,” and “Forever and Always,” the last of which asks her ex, “Was I out of line? Did I say something way too honest, made you run and hide like a scared little boy?”
One year later, while hosting Saturday Night Live, Taylor apparently still held a grudge. “You might think I’d bring up Joe, that guy who broke up with me on the phone,” she sang. “But I’m not going to mention him in my monologue. Hey Joe! I’m doing real well and I’m hosting SNL—but I’m not going to write about that in my monologue.”
But a lot can change in a decade. In May 2019, Taylor returned to Ellen. During a segment called “Burning Questions,” DeGeneres asked her guest to name the most rebellious thing she did as a teenager.
“Probably when I put Joe Jonas on blast on your show,” Swift said. “That was too much… We laugh about it now but that was some mouthy—yeah, just some teenage stuff there.”
That’s not to say she doesn’t still rely on their short-lived romance for material. Fans suspect that the song “Invisible String” on her 2020 album Folklore is about Jonas. “Cold was the steel of my axe to grind / For the boys who broke my heart,” sings Swift. “Now I send their babies presents / Gold was the color of the leaves / When I showed you around Centennial Park / Hell was the journey but it brought me heaven.”
In March 2009, Taylor briefly dated actor Lucas Till. The two met on the set of Hannah Montana: The Movie, but the flame flickered out after just one month.
“We dated for a little bit. But, there was no friction because we were too nice,” Till told MTV News in 2019. “We just really both liked each other … [but] most relationships work out cause you get along and then you don’t, and then you make up and it’s passionate, and with us I really just liked her as a friend. That’s the only reason that didn’t work out.”
Till managed to escape the relationship unscathed. While there don’t seem to be any songs written about him, he did manage to nab a spot in the music video for her song, “You Belong With Me.”