Most people in my life know that there are two pop culture things I can talk about for days: Gilmore Girls and Taylor Swift. So imagine my surprise when I came across a Tiktok about how every Taylor song can be related to a particular Gilmore Girls scene. So like the completely sane and not at all obsessed person I am, I sent it to my friends and boyfriend, pulled up the “Complete Taylor Swift” playlist on Spotify and the list of all Gilmore Girls episodes, and got to work!
To no one’s surprise, I was able to find a match for nearly every song but to not further expose myself and not to bore you all, here are the top ten Taylor Swift songs that remind me of Gilmore Girls.
The Best Day from Fearless (Taylor’s Version)
Of course, The Best Day had to be the first one! This touching song chronicles Swift’s relationship with her mom–making it the perfect soundtrack to the friendship between Lorelai and Rory. The lyrics take us through stages of life–from being five years old to a grumpy teenager to an adult. It mirrors, in many ways, the journey that we see the Gilmore girls go through as Rory grows.
Standout lyric: I know you were on my side/Even when I was wrong/And I love you for giving me your eyes/Staying back and watching me shine
Nothing New from Red (Taylor’s Version)
If this isn’t college Rory in song form, I don’t know what is. Nothing New explores the anxiety and falling apart that occasionally happens in your twenties. As all Gilmore Girls fans know, Rory went through a serious quarter-life crisis starting at the end of season four; she has a relationship with a married man, drops out of Yale, steals a yacht, and stops talking to her mom. All within the span of a season! Nothing New is often hailed as a gifted kid burnout anthem, which also applies to Rory, who was so bright that she burned out.
Standout lyric: I wake up in the middle of the night/It’s like I can feel time moving/How can a person know everything at 18 but nothing at 22?
The Way I Loved You from Fearless (Taylor’s Version)
The Way I loved You is about being in a relationship with someone “safe” but longing for that passionate, bad boy love…aka Rory all of season two when she’s with Dean, her protective first boyfriend, but is quickly falling for newcomer rebel Jess. It didn’t take me long to pull a song that reminded me of Jess Mariano, who is my favorite out of Rory’s boyfriends. I think this song captures the teenage angst Rory was experiencing in the best possible Way.
Standout lyric: It’s 2:00 a.m. and I’m cursing your name/So in love that I acted insane/ And that’s the Way I loved you
Paper Rings from Lover
It is impossible not to smile while listening to this song–much like the engagement scene where Lorelai asks Luke to marry her. After the build-up of Luke and Lorelai throughout the whole show, it’s such a fulfilling moment! It’s the sweetest thing, and they didn’t need shiny things, just each other.
Standout lyric: I like shiny things, but I’d marry you with paper rings/ Darling, you’re the one I want/ And I hate accidents except when we went from friends to this.
State of Grace from Red (Taylor’s Version)
It’s another Rory and Jess one! State of Grace is probably my favorite Taylor Swift song of all time. This song speaks to how Jess and Rory fall in and out of each other’s lives, but it’s electric every time they’re together. The storytelling perfectly captures the feeling of a tumultuous but beautiful love story.
Standout lyric: So you were never a saint/And I’ve loved in shades of wrong/We learn to live with the pain/Mosaic broken hearts/But this love is brave and wild
Champagne Problems from Evermore
One of the best deep cuts from Evermore, Champagne Problems, tells the story of a denied proposal. As Rory prepares for graduation in season seven, Logan proposes, and Rory says no, she wants to pursue her career. The song is a conversation between the woman who said no and the man who asked, specifically mentioning mental illness and the college experience. It fits Rory and Logan perfectly.
Standout lyric: I never was ready, so I watch you go/Sometimes you just don’t know the answer/’Til someone’s on their knees and asks you
Love Live from Speak Now
I couldn’t make this list without putting a song that reminds me of the quirky town of Stars Hollow. Long Live, specifically, applies to when Lorelai, Michel, and Sookie make their dreams come true and open the Dragonfly Inn. It also conjures up images of town hall meetings, festivals, and Miss Patty’s infamous stories.
Standout lyric: Long live all the magic we made
Love Story from Fearless (Taylor’s Version)
Ah, a Swifite classic! I think of young Richard and Emily with Love Story. We don’t learn that much about their younger days, but what we do know is they met at college, and Richard’s mom, the original Lorelai, disapproved of Emily. I think this song also showcases true and everlasting love.
Standout lyric: We were both young when I first saw you
All You Had To Do Was Stay from 1989
All You Had To Do Was Stay reminds me of when Jess leaves at the end of season three. It explains the heartbreak of a breakup where the other just goes away and touches on the complicated feelings of when that person comes back, as Jess did in season four. In a non-romantic context, it can also be applied to how Luke felt about the Jess situation.
Standout lyric: Now you say you want it back/Now that it’s just too late/Well, it could’ve been easy/All you had to do was stay
I’m only me when I’m with you from Debut
We’ll end on a similar note as we started. I’m Only Me When I’m With You is Taylor Swift’s love letter to her closest family and friends. It has a similar energy to the iconic theme song Where You Lead by Carole King. This show is ultimately about family and community, which makes it so comforting.
Standout lyric: Well, you drive me crazy half the time/The other half I’m only trying/To let you know that what I feel is true/And I’m only me when I’m with you
You can listen to all the songs mentioned below! I hope you enjoyed this interdisciplinary deep dive into my two pillars of pop culture and basically what is playing in my head at any given moment. What songs remind you of your favorite TV show?