History has a funny way of being rewritten once you’re the biggest star on the planet. Everyone knows the names now—Travis, Joe, Jake, Harry. They’re the titans of the Swiftian cinematic universe. But before the private jets and the Eras Tour, there was a guy named Drew Dunlap.
If you aren't a "Debut" era purist, you might have missed him. Honestly, most people mix him up with the other Drew—Drew Hardwick, the "Teardrops on My Guitar" guy who didn't even know she liked him.
Drew Dunlap was different. He was real. He was there. And he’s the reason we have the song that started it all.
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The Freshman Year Breakup That Launched a Career
The year was 2005. Taylor was a freshman at Hendersonville High School in Tennessee. Drew Dunlap was a senior. It was that classic, fleeting high school romance that feels like the world until the graduation caps start flying.
Basically, they dated for about a year. When Drew had to leave for college, they knew it was over. That "end-of-summer" sadness is a trope for a reason, right? Most of us just cry in our cars and move on. Taylor Swift wrote "Tim McGraw."
She actually wrote it in the middle of a math class. She was sitting there, thinking about the fact that Drew was leaving and wondering if he’d remember her when he heard their favorite song. It’s kinda wild to think that a teenage girl’s anxiety about being forgotten by a college boy became the foundation for a billion-dollar empire.
Why the "Two Drews" Confusion Happens
It’s a mess, honestly. Let’s clear it up.
- Drew Dunlap: The actual boyfriend. He inspired "Tim McGraw" and "Our Song." They broke up because of life and distance, not because he was a jerk.
- Drew Hardwick: The classmate. He’s the one mentioned by name in "Teardrops on My Guitar." He never actually dated her; she just pined for him while he talked to her about another girl.
You’ve probably seen the headlines about "Drew" having legal troubles later in life. That was Hardwick. By all accounts, Dunlap stayed pretty much out of the limelight, which is probably for the best when you're the first entry in a very public dating history.
The "Tim McGraw" Effect
When "Tim McGraw" hit the radio, Drew Dunlap wasn't just some guy anymore. He was a protagonist.
Imagine being a college freshman and hearing your ex-girlfriend—who you probably thought was just a "singer-songwriter kid" from high school—singing about your old Chevy and how you hope she's the one you think of when you hear that one specific song.
Taylor eventually told USA Today that Drew actually bought the album. He liked it. He thought it was sweet. His girlfriend at the time? Not so much. Can you blame her? It's gotta be weird to date a guy whose ex is the rising star of country music, singing about how "he said the way my blue eyes shined put those Georgia stars to shame."
The Ghost of Drew in the Vault
For a long time, Drew Dunlap was a footnote. A "Debut" era relic. But then came the re-recordings.
When Taylor started opening the "Vault," fans began dissecting songs like "We Were Happy" and "Don't You." The timeline for these tracks usually points back to 2004 or 2005. While Taylor hasn't confirmed it, many Swifties believe these songs reflect the aftermath of the Dunlap breakup.
"Don't You" is particularly biting. It’s about seeing an ex who is being too nice. It’s that awkward "hey, we're still friends, right?" vibe that feels like a punch in the gut when you aren't over them. Given that Drew and Taylor reportedly stayed on decent terms, it fits the narrative better than her more explosive breakups with guys like Sam Armstrong (who allegedly inspired "Should've Said No").
Why Drew Still Matters in 2026
You might wonder why we’re even talking about a high school boyfriend from twenty years ago.
It’s because Drew Dunlap represents the last time Taylor Swift’s life was "normal." He represents the "Dorothea" of it all—the girl under the bleachers before she became the industry. In recent years, especially with the Folklore and Evermore eras, Taylor has returned to those themes of small-town nostalgia and "the one that got away" because of fame.
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Some fans even theorize that "Tis The Damn Season" is a fictionalized "what if" scenario involving a muse like Drew. What if she’d stayed in Pennsylvania or Tennessee? What if she’d followed the boy to college instead of moving to Nashville and signing with Big Machine?
Actionable Insights for the Casual Fan
If you want to understand the "lore" without getting lost in the weeds, keep these things in mind:
- Check the Lyrics: "Tim McGraw" is the definitive Dunlap song. If you listen closely, it isn't a "breakup" song in the traditional sense. It's a "remember me" song.
- Separate the Drews: If you see a TikTok about "Taylor's ex Drew" being a criminal, that's Hardwick. Dunlap is the "nice" one who went to college.
- The "Our Song" Connection: While often associated with the general high school experience, "Our Song" was written for a talent show during the time she was seeing Drew. It captures the frantic, breathless energy of that first real relationship.
The reality is that Drew Dunlap is likely living a very normal life somewhere, probably telling people at parties that he’s the guy in the song—and half of them probably don't believe him. But for those who track the architecture of Taylor’s songwriting, he’s the original blueprint. He wasn't a "star-crossed lover" or a "toxic" mistake. He was just a high school senior who left for school, inadvertently giving the world the spark that started the fire.
To really see how much he influenced her early work, go back and listen to the Taylor Swift debut album through the lens of a 16-year-old girl who just wants her boyfriend to miss her. It hits different when you realize it isn't just "country storytelling"—it was her actual life.