Despite branding herself as the music industry’s most polarizing celebrity, we can all agree on one thing—Taylor Swift knows how to write a damn good love song. Whether she’s banging out an acoustic ballad about her first crush or crooning into Auto-Tune about her first enduring love, Taylor knows how to turn her personal love stories into universal ones. To put it simply, she hits you right in the feels. In sticking close to a one note melody that lets storytelling shine, Taylor has uncovered the key to love song gold: unabashed honesty and a heavy dose of simple romance.
So, in honor of America’s favorite corporate holiday, Valentine’s Day, I’m ranking Taylor Swift’s greatest love songs. Cue that sappy Spotify playlist, grab your boo, and let's get to celebrating.
5. “Holy Ground” – Red (2012)
Perhaps the most upbeat song on this list, Swift trades in quiet guitar strums for a beat you can tap your feet to in this hidden gem from the Red album. It’s a breezy tune consecrating an ultimately failed relationship, with Swift reveling in its softest, and often best, moments. “Holy Ground” molds the platitude, “Don’t cry because it’s over, smile because it happened” into something concrete and tangible, reminding us all not all break–up songs end in scorn. Swift’s imagery is potent: You can imagine her, all wide–eyes and wind–blown curls, exploring New York City with a boy she thinks will be the one. It’s specific yet shockingly relatable, making it the perfect song for a newly solo Valentine’s Day.
Best Lyric: “Tonight I’m gonna dance / for all that we’ve been through / but I don’t wanna dance / if I’m not dancing with you.”
4. “Our Song” – Taylor Swift (2006)
The first Swift song to populate mainstream radio, “Our Song” sits at the center of the Swiftie Canon. What started as a last–minute original for a high school talent show may actually be one of her most perfect songs. Yes, it sounds like high school—all youthful energy, conspicuous meetings, and grand displays of affection we’d probably be too embarrassed to accept now. But perhaps that’s the song’s greatest strength. “Our Song” transports listeners back to time when “long–distance” wasn’t a word in our relationship zeitgeist and our biggest worry was decided which song to request at prom. It’s simple, sweet, and tremendously catchy, smoothing out the edges of a first relationship.
Best Lyric: “I’ve heard every album / listened to radio / waiting for something to come along / that was as good as our song.”
3. “New Years Day” – Reputation (2017)
A return to the sound of the “Old Taylor,” “New’s Year Day” ends Reputation with an ode to commitment and perpetuity. It reads like handwritten wedding vows, with Swift boiling down all of our romantic hopes and dreams into one moment. Ultimately, we all want someone to clean up bottles with us on New Years day, to stay after last call or the cab ride has ended, and to remain through life’s monotony. It’s one of the few Swift songs that doesn’t romanticize a single thing. It’s honest, and with minimalist production, sounds like a peak into Swift’s diary.
Best Lyric: “I want your midnights.”
2. “You Are in Love” – 1989 (2014)
In a departure from her signature candid style, Swift uses “You Are in Love” as a window into not one of her relationships, but of one she views as “the benchmark for true, real love.” It catalogues the slow burn of producer Jack Antonoff’s five year relationship with acclaimed writer and Swift squad member Lena Dunham, emphasizing that love is a process, not a destination. A bonus track on 1989, this song sounds like a secret. Swift sings in hushed tones with a breathy finish, encasing listeners in a reverie for four minutes and 28 seconds. “You Are in Love” is an idyllic preview into what the future can look like, and I cannot imagine a Valentine’s Day playlist without it.
Best Lyric: “One night he wakes / strange look on his face / pauses and says / ‘You’re my best friend.’”
1. “Enchanted” – Speak Now (2010)
When I was 9 years old, I thought “Enchanted” was what my first kiss was supposed to sound like, and it's become the standard I hold every potential suitor to. If our first date doesn’t feel like the song’s crescendoing bridge, teeming with heady anticipation, I know it’s not meant to be. And while that probably says more about who I am than it does the song, let my anecdote be evidence of this — “Enchanted” reminds us to never settle. With a swirling melody and imagery straight out of The Favourite, this crown jewel adds a new dimension to the age–old Prince Charming fantasy. “Enchanted” is Swift at her best, spinning a yarn that combines the spellbinding wonder of love–at–first–sight with lingering vulnerability. It’s a modern–age fairy tale, a proximate fantasy, and the only song you should replay on Valentine's Day.
Best Lyric: “Please don’t be in love with someone else / please don’t have somebody waiting on you.”
