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Guys it’s been 16 years of this legendariness. I know some of you are barely older than her. She’s your older sister, your mother, the confidante you never had.

Co-written with Liz Rose & produced by Nathan Chapman — so many phenomenons in the music industry owe royalties to this song.

The debut era in general pioneered a reassessment of the “seriousness” and validity of The Experience of Being A Teen Girl & the authenticity and artfulness in how this song was arranged helped advance that conversation beyond a dismissal of young female hysteria.

It also tapped into an untapped market — a market taylor was told by various label executives didn’t exist — that TS herself did not understand. Initially, she recognized the hunger for a young girl’s country writing perspective.

What she didn’t realize at the time but became clear to her over the years, is that this gap wasn’t a genre-specific phenomenon. The Taylor Swift gospel spread far and wide in those early years. People who had no interest in country at all were tuned in and enraptured.

This song also depicted her earliest pop inclinations — critics responded with hesitance to her “authenticity” as a country performer when this song came out, and those criticisms never really stopped coming.

And I guess they were right. This IS a pop song. If Taylor had tried to be a by the playbook country artist, we wouldn’t be where we are today. The first-person, present tense storytelling of this song laid the foundation of her greatest skills.

Enough rambling from me — I am so grateful to this song, and I have so many fond memories of pining after straight boys with girlfriends in my room, playing this on repeat.

What’s your journey with this song?! I would love to hear it!

— Zack

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Comments

second year doctoral student in swiftology

There was a period in which the only three "slow dances" played in the school gym dances were Bubbly, No One, or Teardrops. I didn't know debut that well at the point, but the ubiquity piqued my interest... and so I spent my 99 cents from my apple gift card. When I later went to burn some mix CDs for a birthday party favor, I learned I could only burn 7 copies of the same playlist before I had to re-buy the songs. And so I remain the proud owner of 3 .mp3s titled "Teardrops on my Guitar1" "Teardrops on my Guitar2" and "Teardrops on my Guitar3" ...

Reina Lemus

I have a vivid memory of hearing Teardrops for the very first time at 13 in a McDonald’s (lol) and thinking, “who IS this girl??” I was an avid country music hater but the song tapped into something in my pining, unrequited-crushing, afraid-to-talk-to-boys little brain. I didn’t become a real fan until Fearless (from which point I would say “I HATE country except Taylor Swift”) hearing Teardrops for the first time is still a core memory.

Maggie Thompson

My mom was super into country music/Rascal Flatts so she got me taylor's debut CD and I remember I used to listen to teardrops while playing this horse game called Pony Friends on the Nintendo DS and I was living my 9 year old horse girl FANTASY while living in the suburbs 😂 when I hear teardrops and our song....the nostalgia is overpowering like it's CHEMICAL 😭😭😂😂

GW

I’m from the UK where country music is basically never played on the radio or TV. But for some reason my mum had a basket of CDs in the house and I gravitated towards her copy of Wide Open spaces by The (Dixie) Chicks. I ended up in a YouTube hole listening to all their music. This was around 2005/06 when Not Ready To Make Nice was released so they were popping off and I was OBSESSED. My YouTube recommendations eventually turned into a stream of country music songs, none of which had the same hold on me like The Chicks… Until one day in 2007 this barbie-looking blondie with perfect ringlets started appearing in thumbnails on the feed. Instantly, Our Song had a chokehold on me and will forever be top 3 for me. But Teardrops was that deepcut I needed at the time. We all had A DREW. What can I say- I’m just a country loving faguette 🏳️‍🌈🤠 Me, my brother and mum are seeing The Chicks in June to fulfil our country needs, since Ms. Thing refuses to release international dates. 😂😂

GW

Side note: remember when Taylor said that Drew showed up on her driveway after the song was released? Do we think that actually happened or was that a classic swift white lie?

Ana Facha

i don't remember exactly when i first heard it, but i must've been 10? right before fearless came out, and oh boy did this song have a hold on me for a solid 4 years afterwards. i still don't remember how i came across it exactly, but the music video was burned into my brain and led me to discover the whole of debut. should a 11 year old have been sobbing in the shower to "i'll put his picture down and maybe get some sleep tonight"? no, but my pre-teen ass was incredibly dramatic and teardrops on my guitar enabled my main character in a music video tendencies in a way very few songs have since.

Cameron

This is still one of my all time favourites from Taylor… I feel like it’s got such beautiful imagery, the lyrics are simple but tasteful and hit right… if the Gaylors had any brain cells they would see THIS is the “queer-coded” song in her discography, if there’s any… Taylor is not only suffering from unrequited love, but she seems almost expectant of it and jaded by it, which idk if most straight people are expectant of or jaded by rejection, but EVERY gay kid is… Teardrops is more of a gay anthem than YNTCD ever could be

Mia Bates

I heard this song for the first time after in 2010, after love story hit uk radio, and I was 12/13 and very “im not like other girls I don’t like it” with love story in 2008, but then I got to high school in 2010 and had my first proper huge crush on a guy and the girl I sat next to in my home room class was super into Taylor Swift, and she was like “Taylor’s new album speak now is amazing, you should listen to these songs if you don’t like love story” she wrote me a list with the best day on it, better than revenge, but also snuck on hey Stephen and enchanted - and because I was suddenly head over heels for a guy at 14 I suddenly clicked what Taylor was saying with the latter two songs and was obsessed 😂 I then absolutely loved both speak now and fearless from then on, and went back to find earlier hits… and that’s when I heard Tim McGraw, our song and teardrops. Was absolutely obsessed with her outfits and styling in these videos 😍

Sarah

I suspect my experience is going to be different to (most?) people here. I turned 40 last year, so I was 24 when this came out. I didn’t discover Taylor until 2014, but when I went back to catch-up on her discography, this song immediately sent me back to that place of pining over the wrong people in high school. There is something about this song that can touch you whatever age you are when you first listen to it.

Tal

Kate G

I was super into MTV back in 2007. I remember seeing this video, thinking who is this chick, she’s beautiful and plays the guitar. I wanted to know everything about her! I owe so much to debut, how it shaped how play and used to write music. ❤️❤️❤️

abby

“so i drive home alone as i turn out the light ill put his picture down and maybe get some sleep tonight” a certain popstar who has her drivers license could literally never……..

Kellie Funnell

I remember vividly when I first heard this song! My baby sitter who was too old to be my baby sitter anymore…more like a big sis (I was 14) was taking me up to her college in Tennessee to hang out with her for the weekend and we were driving in her beat up car and she had the cd. I just wanted to listen to teardrops and our song over and over but she was obsessed with picture to burn lol. Let’s keep talking about when you heard songs for the first time!! I have so many memories

Christina Guzman

Hi! I’m new and old (age). My daughter was a Swiftie so I was by default. We saw a Fearless concert. It was amazing! Taylor in the rain beating those drum things 🫶🏻. Eventually my daughter moved to boy bands. We saw One Direction too. 😳 That concert was ridiculous. Now my kids are all grown. I’m working on my doctorate and if I ever manage to finish, it will be thanks to you because y’all are always in my ear when I’m studying or writing. I have time to experience full time Swiftiehood. I was so busy teaching and raising kids but always aware and a fan of Taylor. Long story to say that I am loving listening to your content and discovering all the lore. You guys are amazing!