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The Boys Taylor Swift Dated In High School || Debut Song Deep Dives Part 2 episode artwork

EPISODE · Aug 26, 2025 · 1H

The Boys Taylor Swift Dated In High School || Debut Song Deep Dives Part 2

from Typical Tuesday Night || A Taylor Swift Podcast · host Karli + Jess

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!SPONSORS:Fazit (use code TTN15 for 15% off) // https://shareasale.com/r.cfm?b=2350715&u=4555276&m=142497&urllink=&afftrack=Clean Simple Eats (use code TTN10 for 10% off) // https://glnk.io/54jl/ttn Taylor Swift Songs || Taylor Swift Podcast || Taylor Swift || Taylor Swift Debut AlbumSend us Fan MailSupport the showFollow along to hear a new Taylor Swift related episode every single Tuesday.Watch our episodes on YouTube!Follow Us On Social Media:Typical Tuesday Night Podcast @typicaltuesdaynight.podcastKarli @everyday_ellisJess @jess.taitJoin our Patreon for bonus episodes and exclusive Taylor Swift group chat!Shop Our Merch!Feel free to contact us at [email protected]

What this episode covers

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...

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The Boys Taylor Swift Dated In High School || Debut Song Deep Dives Part 2

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How long is this episode of Typical Tuesday Night || A Taylor Swift Podcast?

This episode is 1 hour and 0 minutes long.

When was this Typical Tuesday Night || A Taylor Swift Podcast episode published?

This episode was published on August 26, 2025.

What is this episode about?

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...

Can I download this Typical Tuesday Night || A Taylor Swift Podcast episode?

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