Taylor Swift’s High School Crush Unsuccessfully Tried To Connect With Her After Hearing This Hit Single From 2007

In 2007, Taylor Swift released “Teardrops On My Guitar”. Her second single, and first Top 15 hit, “Teardrops On My Guitar” followed “Tim McGraw”, her debut single.

Swift wrote “Teardrops On My Guitar” with Liz Rose. The song, like much of Swift’s music, is very autobiographical, about a boy she liked in high school. Only 17 years old when “Teardrops On My Guitar” was released, it is about a boy named Drew, later revealed to be Drew Hardwick, whom Swift mentions multiple times in the song. 

“Teardrops On My Guitar” says in part, “Drew walks by me / Can he tell that I can’t breathe? / And there he goes, so perfectly / The kind of flawless I wish I could be.” 

Swift later reveals that not only was “Teardrops On My Guitar” about a boy, Hardwick, whom she had a crush on, but it actually propelled him to eventually reach out to her. Unfortunately for him, it was too late, as by the time he connected with Swift, the spark had already passed for her.

What Taylor Swift Says About the Boy Who Inspired “Teardrops On My Guitar”

Hardwick was dating someone else when this song came out. Two years later, he was suddenly single, but it was too late for Swift.

“About two years after the album came out in the States, he showed up in my driveway,” Swift recalled. “Apparently he and his girlfriend had broken up, so that was his first stop when he was back in town. I was like, ‘You are so late, you know. If you’d stopped by right after the album came out then that would be one thing, but…’ I remember reading on his MySpace page one time, ‘My name’s Drew, and I have a famous song written about me. Email me, and I’ll give you details.’ I was like, right, wow, note taken.”

Swift later admits the timing of him dropping by seems a bit suspicious to her.

“I have theories about what he was doing,” Swift later shared. “He had his friend with him, so maybe he was trying to prove to people that the song really is about him or whatever. Or maybe he was really trying to be friends. Or maybe he thought I was still pining away from him. Whatever!”

If “Tim McGraw” put Swift on the proverbial map, it’s “Teardrops On My Guitar” that showed just how autobiographical Swift would go in her music. After this song, she released “Our Song”, “Picture To Burn” and “Should’ve Said No”, all personal songs.

Photo by Ethan Miller/Getty Images

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