Taylor Swift and Gilmore Girls: Which Songs Relate to Every Character?

A matchup of Taylor Swift songs that relate to our favorite Stars Hollow residents

Autumn leaves falling down like pieces into place

Remarkist came to be because of a TV show we all know and love, Gilmore Girls, when actor John Cabrera–who had never seen the show before April of 2021–decided to watch all 153 episodes with fans. In celebration of Taylor Swift, we decided to bring Taylor to Stars Hollow (she’d probably fit in nicely there–can’t you just see her joining the Town Troubadour?) We came up with a list of songs to match up with our fave Gilmore characters and couples. 💜

Lorelai Gilmore - “The Best Day” and “Lavender Haze”

“The Best Day” reflects the loving and supportive relationship between a mother and daughter👩‍👧, which is central to Lorelai’s character. But beyond motherhood, one thing we appreciate about Lorelai Gilmore–and we also see in “Lavender Haze”–is the defiance against societal norms, particularly those related to traditional female roles. The line “Surreal, I’m damned if I do give a damn what people say” encapsulates Lorelai’s determination to follow her own path despite pressures. As a single mother who left her affluent family to lead an independent life, “No deal, the 1950s shit they want from me,” reflects Lorelai’s rejection of the traditional, conservative values of her parents. Lorelai vehemently opposes the high-society life they represent, marked by materialistic comforts, superficiality, and rigid expectations. Instead, she yearns for a life defined by her own rules, symbolized by the “lavender haze” - a state of tranquility and independence produced by massive amounts of coffee. ☕️ “All they keep asking me is if I'm gonna be your bride/The only kind of girl they see is a one-night or a wife,” perfectly mirrors Lorelai’s romantic endeavors. Her relationships, particularly with Rory’s father Christopher, and diner owner Luke Danes, are often scrutinized by others. Despite the constant pressure and expectations to conform, Lorelai remains steadfast, refusing to let others define her worth or path.

Rory Gilmore - “Fifteen” and “Bejeweled”

The theme of innocence, growing up, and coming of age in “Fifteen” closely relates to Rory’s journey throughout the series. For later in her life, “Bejeweled” is also a perfect picture of the pivotal moment she adorns Emily’s jewelry 💎 and she walks into the room and makes the whole place shimmer ✨ to the point of causing Dean to realize he isn’t worthy of her. The shimmer that night is so powerful it also deeply escalates her friendship with Logan, marked by his bold gestures throughout the evening. And well, if we were to ask her about Dean picking her up, she’d respond, “I don’t remember,” as she had completely forgotten him. Familiarity had indeed bred contempt; remember he entertained her on a date in his parents’ basement, but she was destined to be held in the heart of a penthouse.

Emily Gilmore - “Anti-Hero” and “Mastermind”

“Anti-Hero,” a track renowned for its exploration of masked identities and concealed motives, holds an uncanny mirror to Emily Gilmore’s character. As a wealthy 💵 matriarch, Emily’s life is one of privilege, but it is also steeped in the expectations and obligations that come with such standing. Taylor’s lyrics, “covert narcissism disguised as altruism,” capture the essence of Emily’s complex persona. While she appears to be driven by altruistic motives, Emily often uses her benevolence to manipulate and assert control and maintain her status. Emily’s character, like the protagonist in “Anti-Hero,” navigates a world where appearance and reality often diverge. Her actions, seemingly political (or as Taylor might say, “congressional”), sometimes carry undertones of significant communal narcissism, a trait masked by her social standing and benevolence. 

“Mastermind” paints the picture of an individual who manipulates situations and people to her advantage, intentionally and methodically. Emily is known for her strategic thinking, which she uses to control situations and steer them in the direction she desires. The line “I laid the groundwork and then just like clockwork 🕰, the dominoes cascaded in a line,” encapsulates Emily’s nature of planning and foresight. This is seen time and again in the show, as she carefully sets plans into motion to influence her family’s decisions.

Richard Gilmore - “The Lucky One”

In “The Lucky One,” Taylor paints a vivid picture of the glamorous yet challenging life of a person who has witnessed the glitz and the grit of high society 💵 🥃 and provides a striking reflection of Richard’s character. From the outside, Richard appears fortunate and blessed, living a life many would aspire to have. However, beneath this facade, he continually grapples with personal challenges and the weight of his success. This duality aligns perfectly with the song’s narrative, which explores the paradox of privilege.

Trix - “Marjorie”

Known as Lorelai “Trix” Gilmore, the great-grandmother 👵🏻 of Rory and mother of Richard, this character carries a significant influence in the Gilmore family’s life. Her strong presence, even when she's not physically present, mirrors Taylor’s lyric, “And if I didn’t know better, I'd think you were talking to me now.” This lyric signifies the enduring presence of loved ones, an idea that reflects Trix’s influence on the Gilmore family. “Marjorie” also discusses the concept of legacy and the impressions left by influential figures.  Trix’s character can be reflected in the song’s exploration of regret and reconciliation. Trix’s relationship with her family, particularly with her daughter-in-law, Emily, is riddled with conflict. Marjorie’s legacy for Taylor are the lyrics, “Never be so polite, you forget your power. Never wield such power, you forget to be polite.” This echoes Trix’s dominant personality and her complicated relationships, illustrating the potential consequences of power without consideration.

Luke Danes - “Willow”

Luke Danes, the rugged and reliable diner owner in Stars Hollow, is a pillar of constancy in the show. His deep-seated love for sorceress Lorelai Gilmore serves as a cornerstone of his character, enduring through thick and thin, much like the steadfast love depicted in “Willow.” Taylor’s lyric, “I’m begging for you to take my hand, wreck my plans, that’s my (wo)man,” could very well articulate Luke’s feelings towards Lorelai. Luke has often altered his plans and prioritized his love for Lorelai. To Luke, Lorelai is a “mythical thing,” the embodiment of a free spirit who chooses her own path, and a whirlwind of wit and charisma that captivates him. Much like the enchanting allure of a mythical creature, Lorelai’s vivacious personality, and fast-talking charm weave a spell Luke cannot resist. Lorelai refuses to be confined by societal norms or expectations, and the line, “life was a willow, and it bent right to your wind,” parallels an individual swaying with the wind of her magical manifest desires. However, despite her penchant for freedom, Luke serves as her anchor ⚓️, the reliable “train” that can bring her home when she needs solace. Taylor’s lyric, “The more that you say, the less I know, yet, wherever you stray I follow,” encapsulates Luke’s feelings towards Lorelai beautifully. Lorelai often uses her rapid-fire conversational talent as a smokescreen, a bait-and-switch mechanism to divert from the heart of matters. Like Taylor’s protagonist reflects “Every bait and switch was a work of art.” He’s not even mad, he’s impressed because he is “all in.”

Sookie St. James - “Paper Rings”

Sookie’s upbeat and bubbly personality, along with her love for her friends and her husband, Jackson, are reflected in this happy, up-tempo love song. “Paper Rings” is an upbeat track that captures the exhilarating feeling of being in love. 💘 It’s a song that conveys a sense of devotion so profound that materialistic aspects, such as a diamond ring 💍, are of no consequence. Taylor sings, “I like shiny things, but I’d marry you with paper rings,” signifying a love that is profound, unpretentious, and genuine.

Lane Kim - “22”

“22” is a jubilant celebration 🎉 of the highs and lows of being 22, a confusing yet liberating age that Taylor Swift labels as “miserable and magical.” The energetic and colorful song encapsulates the oscillating emotions of this age, much like Lane’s life as she navigates her early twenties. As a young woman, Lane grapples with her dreams of being a drummer 🥁 and reconciling this with the stringent expectations of her conservative mother. Like the song’s narrative, Lane’s life is full of emotional ups and downs, fears, and aspirations. Yet, she faces them with a youthful spirit, mirroring Taylor’s lyrics, “We’re happy, free, confused, and lonely in the best way.” The song also reflects Lane’s relationship with her band, Hep Alien, and her roller coaster romantic life with those rockers. The camaraderie and shared passion within the band, coupled with her romantic entanglements, echo the exhilarating, carefree, yet slightly chaotic energy of “22.” Moreover, “22” captures Lane’s journey of self-discovery. As the series progresses, Lane becomes more comfortable embracing her love for music, rebelling against her mother’s traditions, and finally finding her place in the world, encapsulating Taylor’s notion of “dancing like you’re 22.”  

Paris Geller - “The Last Great American Dynasty”

Paris’s character is often associated with high society, just like Rebekah Harkness in the song. The song tells the tale of Rebekah Harkness, a woman known for her wealth, societal status, and fun party crashing. The song’s narrative holds a striking resemblance to Paris Geller’s character arc - a young woman entrenched in high society, ambitious, intelligent, and unabashedly herself. Paris is well known for her “list of enemies.” 📝 If we told you about the episode you missed where she “dyed the neighbor’s dog key lime green,” you’d believe us, right? Paris Geller is a character whose life revolves around high societal expectations and a relentless pursuit of success. She is often perceived as too aggressive or too driven, similar to how Rebekah is described in Taylor’s song. Paris has a fierce 🔥 personality and isn’t afraid to be assertive or even intimidating. She can be intense in relationships, and “Last Great American Dynasty” can be seen as a reference to Paris’s relentless drive and how she can be overwhelming at times. If you heard Rory mention an evening as “Paris had a marvelous time, ruining everything,” you’d believe it right?  Taylor’s lyrics, “There goes the last great American dynasty/who knows, if she never showed up, what could’ve been,” could be interpreted as a nod to Paris’s ambition and struggles with her Harvard “dynasty.” Despite the societal norms and expectations, Paris remains unapologetically herself - fiercely ambitious, strong-willed, and passionate.

Dean Forester - “White Horse”

Dean, Rory’s first boyfriend, initially seems like a dream come true–a knight in shining armor 🤴 in the world of teenage romance. Taylor’s lyrics, “I’m not a princess, this ain’t a fairytale. I’m not the one you’ll sweep off her feet, Lead her up the stairwell,” resonate with Rory’s journey. As Rory’s worldview evolves, she begins to understand the complexities of love, realizing that fairy tale endings often exist only in storybooks.

Jess Mariano - “Exile”

While we also were quite torn on how to feel about Jess, we all would agree the feeling of being an outsider in “Exile” also corresponds to Jess’s struggle to integrate into the close-knit community of Stars Hollow. His aloofness and rebellious streak often set him apart from the rest, culminating in him frequently landing in trouble. Moreover, the song’s exploration of being out of sync with a loved one mirrors Jess’s relationship with Rory. Despite their shared attraction, Jess and Rory never seem to align, their timing always off, much like the estranged lovers in “Exile.” Taylor’s lyrics, “You never gave a warning sign,” ⚠️ echo Jess’s constant struggle to communicate and connect with Rory, eventually leading to their relationship’s downfall.  You can almost hear Rory respond that she indeed “gave so many signs.”  Taylor’s lyric, “I think I've seen this film before, and I didn't like the ending,” mirrors Jess’s recurring pattern of disappointment and alienation though many of his relationships.

Logan Huntzberger - “Champagne Problems”

A hauntingly beautiful ballad, “Champagne Problems” 🍾 narrates the tale of a privileged life, marked by the complexities of interpersonal relationships and personal struggles. Logan, hailing from a wealthy family, is a character who seems to have it all on the surface. He presents a lifestyle of means, reflected in the lyric, “Dom Pérignon, you brought it.” However, beneath this surface of privilege and wealth lies a multitude of personal issues. Despite his outward charm and affluence, Logan grapples with his family’s expectations, the pressure to conform, and his quest for personal identity. This dichotomy between his external life and internal struggles resonates deeply with Taylor’s song, especially the lyric, “Your heart was glass, I dropped it.”

Kirk Gleason - “Me!”

“Me!,” an upbeat, self-love anthem 📣 from Taylor, celebrates the power of individuality and self-acceptance. It encapsulates the joy of being unique and not conforming to society’s expectations, themes that aptly resonate with Kirk’s character. Kirk Gleason, one of Stars Hollow’s most eccentric and beloved residents, embodies a unique blend of quirks and idiosyncrasies that set him apart from the crowd. Over and over we celebrated how his character marches to the beat of his own drum. Instead, Kirk embraces his uniqueness, much like in “Me!” where Taylor declares, “I'm the only one of me/Baby, that’s the fun of me.” Taylor’s lyrics, “I promise that you’ll never find another like me,” could very well serve as Kirk’s mantra. From his assortment of odd jobs to his unique perspective on life, Kirk exudes individuality. His narrative is a testament to his singularity in the town of Stars Hollow, just as Taylor’s song champions the beauty of being oneself. Furthermore, the song’s lively and playful tone matches Kirk’s character, who often provides comic relief in the series. 

Miss Patty - “Don't Blame Me”  

“Don't Blame Me” echoes the spirited romantic journey of Miss Patty from Gilmore Girls. Taylor’s lyrics, “Don't blame me, love made me crazy. If it doesn’t, you ain’t doing it right,” could be considered Miss Patty’s personal anthem. The song’s unapologetic tone aligns with Miss Patty’s embrace of love’s highs and lows, and her unceasing quest for new romantic adventures, particularly with men in uniform. 🦺

Brian Fuller - “The Lakes”

“The Lakes” is a tranquil ballad that beautifully encapsulates the longing for solace and authenticity. The song explores Taylor’s desire to escape the clamor of fame and seek refuge in nature’s 🌲 serenity, themes that echo Brian’s narrative. Just as Taylor sings about seeking solace “by the lakes,” Brian too seems to find comfort and peace ☮️ in his music and friendships, seemingly unbothered by the chaotic world around him. Brian’s love for playing music 🎵, a significant aspect of his character, resonates with the melodic tranquility of “The Lakes.” Just as Taylor uses her art to convey her feelings and experiences, Brian too uses music as a vehicle for self-expression. This shared love for music establishes a profound connection between the song and Brian’s character, highlighting the universality of music as a means of authentic self-expression. Brian mirrors Taylor’s longing for authenticity in the song. Brian, unlike many other characters, remains untouched by the competitive and fast-paced world around him, choosing instead to stay true to his passion for music and loyalty towards his friends. Similarly, here Taylor expresses a yearning to escape the superficiality of fame and return to a more authentic existence. The protagonist yearning to throw their phone 📱 in the lake has forsaken material cares and always only seems to have three dollars, 💸 much like our beloved Brian. 

Relationships

Rory and Dean - “Everything Has Changed” and “August”

Everything changes when Dean moves to Stars Hollow from Chicago and sets his eyes on Rory. Rory goes from sticking her head in another book, 📕 oblivious to the rest of the world, to noticing Dean. Her life plans of going to Chilton and Harvard are rocked. Why not stay at Stars Hollow High? What’s wrong with going to public school? Who remembers their first love? They bring back so many wonderful feelings that are so hard to forget.

Rory and Jess - “Come Back…Be Here” “Treacherous” “Getaway Car”

Rory is tormented by choosing to stay with her first “love,” or trying something new and exciting with a “bad boy.” Who doesn't want some excitement, a “reckless path” (“Treacherous”) in their life and to fall for a “bad boy?” There is nothing wrong with loving more than one person. But sooner or later, you will need to choose or the choice will be made for you. In the end, do those bad boys stay or run, when life gets too real? You could imagine Rory asking Jess to “come back, be here” when he decides to run 🏃‍♂️ as life gets difficult and he leaves, needing to work on himself. Like Taylor’s protagonists who plot their escape in a “Getaway Car,” Jess and Rory’s romance is a daring deviation from Rory’s stable relationship with Dean. Rory is drawn to Jess’s rebellious spirit and intellectual depth, making their romance an intoxicating escape from her otherwise predictable life. However, the lyrics, “We were jet-set, Bonnie and Clyde, Until I switched to the other side,” reflect the eventual downfall of their relationship. She could say “And that was the last time I ever saw you” many times.

Rory and Logan - more “Champagne Problems”

 A noteworthy theme in the song is that of a broken engagement 💍, with the phrase symbolizing high-class issues that are trivial in the grand scheme of life but significant to those involved. This is mirrored🪞in Rory’s rejection of Logan’s proposal, the event also underscores the societal pressure and expectations they struggle with, highlighting the personal battles referenced in Taylor’s song.  As Taylor laments, “But you’ll find the real thing instead,” Rory and Logan, too, face the harsh reality of their relationship's limitations, encapsulating the pain of love lost.

Rory and Lorelai - “Never Grow Up" and “Blank Space”

“Never Grow Up” is a tender lullaby that Taylor reflects Lorelai's feelings for Rory, especially in the early seasons but again as she says goodbye to her as she leaves for college, a moment that hits us right in the feels. Yet as their relationship progresses, we also see Lorelai’s parentage through the message of “Blank Space:” “Boys only want love if it’s torture/Don’t say I didn’t, say I didn’t warn ya.” Often, Lorelai imparts to Rory that some partners only desire love when it’s difficult or challenging, they are drawn to the chase and the pursuit, which wrong or right, was something we saw in Jess. “So it’s gonna be forever/Or it’s gonna go down in flames:” Lorelai could be cautioning Rory about the fleeting nature of young love. It can seem like it’ll last forever or end dramatically, implying that Rory should be cautious with her feelings. “You can tell me when it’s over/If the high was worth the pain:” Lorelai could be advising Rory that heartbreak 💔 is often a part of love, especially young love, and that Rory should be prepared for the potential pain that could come with her relationship with Dean. “Got a long list of ex-lovers/They’ll tell you I’m insane:” Lorelai could use this line to show Rory that she herself has been through many relationships and has the experience to understand how they can go wrong. “But I got a blank space, baby/And I’ll write your name:” In this context, it could be a warning ⚠️ from Lorelai to Rory that young partners may not always have the best intentions, and they might just be looking for the next name to fill a “blank space.”

Ms. Kim and Lane - “Never Grow Up”  

The line, “Could still be simple” might hint at Mrs. Kim’s wish for Lane to embrace the simple, traditional life she envisages for her, which starkly contrasts with Lane's love for rock music 🎶 and her ambition to break free from her restrictive upbringing. “And even though you want to, just try to never grow up” can reflect the conflict Lane experiences as she matures. She yearns for independence, yet also struggles with the potential impact on her relationship with her mother. 👩‍👧

Lorelai and Luke - “You Are in Love”

“Small talk, he drives/coffee at midnight.” Her love for coffee ☕️ and the countless shared moments at Luke’s Diner, often around midnight, 🕛 affirm their bond and mirror the sentiments of these lyrics. Their anthem “You Are In Love,” echoes the deep-rooted love, comforting familiarity, and resilience in the relationship of Lorelai Gilmore and Luke Danes. The act of sharing coffee serves as their unique love language, illustrating the intimacy they share in the ordinary routine of life. “And when you understand the joke that nobody else has gotten” can particularly be linked to the duo’s unique camaraderie. Lorelai always found one fatal flaw in her suitors: they couldn’t keep up with her humor 😂 like Luke can. Their relationship is laden with inside jokes and shared laughter, a reflection of their deep understanding of each other. “You fight and you talk” reflects their ability to talk through these conflicts, to reach a point of understanding and compromise that fortifies their relationship. The song captures how love can be found in simple, everyday moments, a love that Luke and Lorelai personify. The lyrics “You're my best friend” resonate strongly, as the two have a solid friendship that is the foundation of their relationship. Lastly, the song’s lyric, “I’ve spent my whole life trying to put it into words,” could signify Luke's realization of his love for Lorelai, which he tries to articulate throughout the series.  The couple’s ability to argue yet communicate is a testament to the strength of their bond, making this lyric highly relatable to their love story.

Lorelai and Christopher - “Better Man,” “The One,” and “Cardigan”

In their early relationship, “Better Man” captures the essence of Lorelai’s feelings for Christopher, particularly in the early seasons. As the lyrics say, “I know I’m probably better off on my own/Than loving a man who didn’t know/What he had when he had it.” This aligns with Lorelai’s perspective on Christopher, as he often fails to step up when it matters most. As the series progresses, the couple experiences moments of hope and reconciliation, much like the lyrics suggest: “Sometimes, in the middle of the night, I can feel you again/But I just miss you, and I just wish you were a better man.” Despite their deep-rooted love, the couple eventually recognizes their incompatibility. Lorelai’s struggle to completely sever her ties with Christopher, due to their shared history and daughter, is also depicted in the song: “We might still be in love, if you were a better man.” This resonates with Lorelai’s lingering feelings for Christopher despite their unsuccessful attempts at being together. 

When Lorelai reconnects with Christopher, no matter who she is with, the sentiments of “the one” and “cardigan” resound.

Lorelai and Max -  “Maroon” 

The lines “(Out with) no shoes/Looked up at the sky and it was maroon” captures Lorelai’s spontaneity and desire for love, as she takes a leap of faith with Max. Yet the phrase “The lips I used to call home, so scarlet, it was (maroon)” speaks volumes about the eventual end of their relationship. Despite their passionate moments and Max’s proposal 🌼, Lorelai realizes that she doesn’t feel “at home” with him, leading to their breakup. The lyrics “Carnations you had thought were roses, that’s us” is also an apt metaphor for their relationship. What started as an exciting and promising romance (roses 🌹) ultimately turned out to be something less satisfying and fulfilling (daisies 🌼). “Laughing with my feet in your lap/Like you were my closest friend” encapsulates the bond between Lorelai and Max, as they started as friends and colleagues before their relationship deepened. This could mirror the friendly dynamic between the two in the early stages of their relationship.

Zack and Lane - “Change” 

Zack is the “stereotypical” rocker. 🎸 He parties hard and loves the ladies. When the band needs a drummer 🥁 they answer an ad placed by Lane. Their lead, Dave, leaves to go to college and California, leaving Lane’s heart broken. 💔 Zack and Lane’s story was far from a storybook. Zack doesn’t really notice Lane at first; she’s nothing more than their drummer. Then one day, everything changes. Lane tells Zack she likes him, and the rest is history.

Paris and Rory - “I Can See You”

Throughout the course of the series, Paris and Rory’s relationship can be paralleled to the narrative outlined in Taylor Swift’s “I Can See You.” Starting as competitors, the two have a tumultuous relationship marked by rivalry, slowly morphing into an unexpected friendship-an evolution that reflects the undercurrents of longing, tension, and curiosity present in Taylor’s song. The lyrics, “You brush past me in the hallway, And you don’t think I, I, I can see ya, do ya?” echo the initial stages of Paris and Rory’s relationship. Both brilliant students at Chilton, they start as rivals, brushing past each other in the competitive race towards academic 🎓 success, all the while keeping a watchful eye 👀 on one another. As the song progresses to, “I've been watching you for ages, And I spend my time trying not to feel it,” we see the turning point in Paris and Rory’s relationship. Their rivalry slowly morphs into mutual respect, and eventually, friendship. Paris has been watching Rory, acknowledging her intelligence, and trying to deny the budding friendship. Over time the shared secrets, struggles, and triumphs that Rory and Paris navigate together forges their relationship and though unexpected, become a touchstone in their lives. This closely held bond, just like the clandestine connection in Taylor's song, becomes one of many secrets they share.

Paris and Doyle - “I Knew You Were Trouble” 

Paris navigates her life at high velocity, pushing herself to excel in her academic 🎓 and career pursuits 🔬. Yet, beneath this layer of tenacity and resilience, Paris harbors a profound and beautiful capacity for emotion. This dichotomy is starkly evident in her romantic relationships, particularly her complex entanglement with Doyle McMaster. “I Knew You Were Trouble,” could well serve as Paris’s anthem for her turbulent romantic journey. This song encapsulates the experience of falling for someone, fully cognizant of the impending tumult, yet being powerless to resist the pull of attraction. Taylor’s lyrics, “I knew you were trouble when you walked in...A new notch in your belt is all I’ll ever be,” reveal the protagonist’s awareness of the impending heartache, reminiscent of Paris’s romantic entanglements. In her relationship with Doyle, Paris finds herself in a whirlwind of emotion and turmoil. Doyle, like the character in Taylor’s song, brings both love and trouble into Paris’s life. Furthermore, Taylor’s melody carries a tone of regret and self-blame, themes that echo Paris’s feelings after her breakups and romantic hurdles. Paris often finds herself questioning her choices and reflecting on the part she played in the turbulence of her relationships.

From Lorelai's quest for personal happiness, Rory’s romantic entanglements, to Kirk’s chaos to Luke’s stability, and even the endearing love stories of characters like Sookie and Lane, Taylor Swift’s discography 💿 is a perfect accompaniment to the world of Stars Hollow. This is intended to be interactive 🗣 and a starting point: what song would you pick instead? 🎼 Come chat with us on Discord to discuss!

Want more?

Join us at rmrk*st all month for Taylor Swift content! Make sure you check out the listening parties, watch parties and more we have planned at Remarkist on our app! And if you love games, check out our Instagram for Melodic Mayhem, our bracket-style lyric showdown! You can find and chat with other Taylor Swift fans on our Discord!