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August 26, 2025 60 mins

We love discussing Taylor Swift’s relationships and what we learn about them from the songs that she sings, and today’s podcast episode is no different. We are jumping into the relationship songs from Taylor’s debut album and discussing which songs are about which boy.

Starting with Tim McGraw we give you the details of her relationship with Drew Dunlap and how she created this classic song. We also discuss the breakup songs such as Picture To Burn and Should’ve Said No, sharing who each song is about, fun Taylor Swift facts, our favorite lyrics and more.

Join us weekly as we discuss all things Taylor Swift in the best Taylor Swift podcast around!

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