If you’re a true Swiftie or just a fan of clever wordplay, Taylor Swift riddles are a perfect way to combine fun with your favorite pop icon. These riddles not only challenge your brain but also celebrate the many sides of Taylor from her chart-topping hits to her iconic persona. Taylor Swift Riddles.
Whether you’re looking to entertain friends, break the ice at a party, or just add a bit of musical flair to your day, these Taylor Swift riddles will keep you guessing and smiling. Let’s dive into the lyrical mystery and enjoy the puzzle!
Taylor Swift Songs Riddles
- What Taylor Swift song tells the story of a love that’s “Fearless” but also “Untouchable”? Answer: Fearless
- Which song would Taylor Swift sing about a “Love Story” that never ends? Answer: Love Story
- Which Taylor Swift hit talks about shaking off negativity? Answer: Shake It Off
- In which song does Taylor Swift say, “You belong with me”? Answer: You Belong With Me
- Which Taylor Swift song’s title is also a common phrase used to express regret? Answer: Back to December
- Which song describes a “Blank Space” on a page or heart? Answer: Blank Space
- What song did Taylor sing about an enchanted evening meeting someone new? Answer: Enchanted
- Which song has Taylor Swift reminiscing about the “All Too Well” moments? Answer: All Too Well
- Which Taylor Swift song was inspired by a famous red lipstick color? Answer: Red
- Which song has the famous line, “I remember how we felt sitting by the water”? Answer: Mine
- What song talks about “The Story of Us” and an awkward break? Answer: The Story of Us
- Which Taylor Swift track is about a love that is “Delicate”? Answer: Delicate
- Which song talks about a “Cruel Summer” of heartbreak? Answer: Cruel Summer
- Which song is about a person who “Loves You Like a Love Song”? (trick question: this is actually by Selena Gomez, not Taylor!) Answer: None (It’s by Selena Gomez)
- Which song contains the line “Darling, I’m a nightmare dressed like a daydream”? Answer: Blank Space
- What Taylor Swift song refers to a “New Romantics” lifestyle? Answer: New Romantics
- Which song references a “Tim McGraw” memory? Answer: Tim McGraw
- Which song starts with the words, “I remember when we broke up the first time”? Answer: We Are Never Ever Getting Back Together
- Which song has a title that also means a seasonal color? Answer: Red
- Which song features the lyric, “I got a blank space baby, and I’ll write your name”? Answer: Blank Space
Read More: Sword Riddles 2025
Taylor Swift Albums Riddles
- Which album is known for a “Fearless” reputation? Answer: Fearless
- Which album features the song “Lover”? Answer: Lover
- Which album is called the “Red” album? Answer: Red
- Which Taylor Swift album is named after a year? Answer: 1989
- Which album has the mood of “Folklore” and “Evermore”? Answer: Folklore and Evermore (two separate albums)
- Which album came out before “Reputation”? Answer: 1989
- What album contains “All Too Well”? Answer: Red
- Which album’s cover features Taylor in a dark, moody style? Answer: Reputation
- Which album was released in 2010 and is also a color? Answer: Speak Now (not a color trick riddle!)
- Which album is named after Taylor Swift’s birth year? Answer: 1989
- Which album’s style marks Taylor’s full transition to pop? Answer: 1989
- Which album includes songs like “Cardigan” and “Betty”? Answer: Folklore
- Which album has the theme of heartbreak and revenge? Answer: Reputation
- Which album is a surprise release in 2020? Answer: Folklore
- What album did Taylor release after “Fearless”? Answer: Speak Now
- Which album contains a song called “The Archer”? Answer: Lover
- Which album’s title suggests speaking out? Answer: Speak Now
- Which album marked Taylor’s return to country roots? Answer: Fearless (original and Taylor’s version)
- Which album features a track called “Willow”? Answer: Evermore
- Which album has the song “Look What You Made Me Do”? Answer: Reputation
Taylor Swift Tour Riddles
- Which Taylor Swift tour was called the “1989 World Tour”? Answer: 1989 World Tour
- Which tour followed the “Fearless Tour”? Answer: Speak Now World Tour
- What tour was known for the iconic “Reputation Stadium Tour”? Answer: Reputation Stadium Tour
- Which tour featured elaborate snake imagery? Answer: Reputation Stadium Tour
- Which tour was interrupted by a global pandemic? Answer: Lover Fest (planned but canceled)
- Which tour came right after “Red Tour”? Answer: 1989 World Tour
- Which Taylor Swift tour had a “Speak Now” theme? Answer: Speak Now World Tour
- What tour is Taylor Swift’s longest so far? Answer: Reputation Stadium Tour
- Which tour was promoted by the album “Fearless”? Answer: Fearless Tour
- Which tour was held in arenas rather than stadiums? Answer: Speak Now World Tour
- Which tour featured songs from “Folklore” and “Evermore” in 2021? Answer: There was no tour due to the pandemic, but Taylor did live performances
- Which tour marked Taylor Swift’s first full pop tour? Answer: 1989 World Tour
- Which tour was known for its theatrical storytelling? Answer: Speak Now World Tour
- What tour included the “Reputation” era costume changes? Answer: Reputation Stadium Tour
- Which tour was announced alongside the “Lover” album? Answer: Lover Fest (later canceled)
- Which Taylor Swift tour featured special guest appearances? Answer: 1989 World Tour
- Which tour was the first to have a live-streamed concert? Answer: Reputation Stadium Tour
- Which tour’s setlist had a mix of country and pop songs? Answer: Speak Now World Tour
- Which tour was designed with a “Red” and “White” color theme? Answer: Red Tour
- Which tour celebrated Taylor Swift’s move from country to pop? Answer: 1989 World Tour
Taylor Swift Lyrics Riddles
- “I remember it all too well.” Which song is this lyric from? Answer: All Too Well
- “Cause, darling, I’m a nightmare dressed like a daydream.” From which song? Answer: Blank Space
- “We never go out of style.” Which track has this line? Answer: Style
- “This love is difficult, but it’s real.” What song? Answer: Love Story
- “I’m just gonna shake, shake, shake, shake, shake.” Which song? Answer: Shake It Off
- “You call me up again just to break me like a promise.” Which song is this from? Answer: All Too Well
- “I knew you were trouble when you walked in.” What song? Answer: I Knew You Were Trouble
- “I don’t wanna touch you, I don’t wanna be just another ex-love.” Which song? Answer: Delicate
- “And I don’t know why, but with you I’d dance in a storm in my best dress.” What song? Answer: Fearless
- “I’m shining like fireworks over your sad, empty town.” Which song? Answer: Dear John
- “Band-aids don’t fix bullet holes.” Which song? Answer: Bad Blood
- “All the king’s horses, all the king’s men.” Which song? Answer: All Too Well
- “I had a marvelous time ruining everything.” What song? Answer: The Last Great American Dynasty
- “I’m a crumpled-up piece of paper lying here.” Which song? Answer: All Too Well
- “Time won’t fly, it’s like I’m paralyzed by it.” Which song? Answer: All Too Well
- “I remember how we felt sitting by the water.” Which song? Answer: Mine
- “This night is sparkling, don’t you let it go.” Which song? Answer: Fearless
- “You made a rebel of a careless man’s careful daughter.” Which song? Answer: Mine
- “We’re happy, free, confused, and lonely at the same time.” Which song? Answer: 22
- “I was enchanted to meet you.” Which song? Answer: Enchanted
Taylor Swift Fans and Culture Riddles
- What nickname do Taylor Swift’s fans proudly use? Answer: Swifties
- What social media platform does Taylor Swift often use to connect with fans? Answer: Instagram (also Twitter)
- What is Taylor Swift’s signature color often associated with her “Red” album era? Answer: Red
- Which awards show famously saw Taylor Swift’s “You Belong With Me” video win? Answer: MTV Video Music Awards (VMAs)
- What is the name of Taylor Swift’s cat often seen on her social media? Answer: Olivia and Meredith
- Taylor Swift’s move from country to pop is often called what? Answer: The Pop Transition
- What phrase is commonly used by fans for Taylor’s cryptic social media hints? Answer: Easter Eggs
- What Taylor Swift era is associated with snakes and a darker image? Answer: Reputation Era
- Which Taylor Swift era is known for cozy, indie vibes? Answer: Folklore/Evermore Era
- Taylor Swift often writes songs about what type of experiences? Answer: Personal relationships and emotions
- What is the title of Taylor Swift’s documentary released on Netflix? Answer: Miss Americana
- Which song famously made Taylor Swift the youngest Album of the Year Grammy winner? Answer: Fearless
- Taylor Swift is also known for her advocacy for what? Answer: Artist rights and music ownership
- What style of music did Taylor Swift begin her career with? Answer: Country
- What year was Taylor Swift born? Answer: 1989
- Taylor Swift’s “All Too Well” is known for what? Answer: Emotional storytelling
- What is Taylor Swift’s favorite way to surprise fans? Answer: Secret sessions and surprise album drops
- Taylor Swift’s cat Meredith is named after which celebrity? Answer: Meredith Grey from Grey’s Anatomy
- What’s the name of Taylor’s musical production company? Answer: Taylor Swift Productions
- What is the symbol often associated with Taylor’s “1989” era? Answer: Polaroid pictures
Taylor Swift Awards and Achievements Riddles
- How many Grammy Awards has Taylor Swift won as of 2024? Answer: 12 (Please verify latest count)
- Which song won Taylor Swift her first Album of the Year Grammy? Answer: Fearless
- Taylor Swift was the first woman to win Album of the Year Grammy how many times? Answer: Three times
- What record did Taylor Swift break with her “1989” album? Answer: First female artist to have three albums sell over 1 million copies in the first week
- Which Taylor Swift song won Video of the Year at the 2015 VMAs? Answer: Bad Blood
- Which Taylor Swift album was the fastest-selling female album in U.S. history? Answer: 1989
- What prestigious award did Taylor Swift receive from the Country Music Association in 2009? Answer: Entertainer of the Year
- Which Taylor Swift album won the Grammy for Best Pop Vocal Album? Answer: 1989
- Taylor Swift was honored as Artist of the Decade by which organization? Answer: American Music Awards
- Which music video features Taylor Swift and rapper Kendrick Lamar? Answer: Bad Blood
- What milestone did Taylor Swift achieve on Spotify in 2017? Answer: Most-streamed female artist globally
- Taylor Swift holds the record for most Billboard Music Awards won by a female artist. True or False? Answer: True
- Which song earned Taylor Swift a Golden Globe nomination for Best Original Song? Answer: Beautiful Ghosts
- Taylor Swift won her first Emmy Award for what? Answer: Original song for a TV special
- How many times has Taylor Swift been nominated for the MTV VMA Best Female Video? Answer: Multiple times (exact number varies)
- Which Taylor Swift song was named the Billboard Hot 100 Song of the Year? Answer: We Are Never Ever Getting Back Together
- Taylor Swift was the youngest artist to sign a publishing deal with which company? Answer: Sony/ATV Music Publishing
- Taylor Swift’s “Folklore” won Album of the Year Grammy in what year? Answer: 2021
- Which song from “Evermore” was nominated for a Grammy? Answer: No Body, No Crime
- Taylor Swift is known for breaking records in which music chart? Answer: Billboard Hot 100
Taylor Swift Fun Facts Riddles
- What instrument does Taylor Swift famously play? Answer: Guitar
- Which Taylor Swift song was inspired by a high school crush? Answer: You Belong With Me
- What city is Taylor Swift originally from? Answer: Reading, Pennsylvania
- Taylor Swift has a love for which type of cats? Answer: Scottish Fold cats
- Which Taylor Swift song features a cameo by actor Sean O’Pry? Answer: Blank Space
- Taylor Swift is known to write songs about what? Answer: Personal experiences and relationships
- What is Taylor Swift’s favorite color? Answer: Blue (varies based on interviews)
- What hobby does Taylor Swift enjoy besides music? Answer: Cooking and baking
- Which Taylor Swift song was her debut single? Answer: Tim McGraw
- What is the name of Taylor Swift’s first album? Answer: Taylor Swift
- Taylor Swift’s famous “squad” includes which type of people? Answer: Friends from music and acting industries
- What nickname did Taylor Swift give her fans? Answer: Swifties
- Which Taylor Swift song was featured in the movie “The Hunger Games”? Answer: Safe & Sound
- What type of writing tool does Taylor Swift prefer for her lyrics? Answer: Pen and paper
- Which Taylor Swift song is about a “Miss Americana”? Answer: Miss Americana & The Heartbreak Prince
- Taylor Swift’s “All Too Well” 10-minute version was released in which year? Answer: 2021
- What is Taylor Swift’s middle name? Answer: Alison
- Which sport did Taylor Swift play in her youth? Answer: Tennis
- Taylor Swift is known for what signature hairstyle? Answer: Blonde hair with bangs
- What philanthropic work is Taylor Swift involved in? Answer: Education and disaster reliefe
Taylor Swift Collaborations Riddles
- Which artist joined Taylor Swift on the track “Everything Has Changed”? Answer: Ed Sheeran
- Who collaborated with Taylor Swift on “Bad Blood (Remix)”? Answer: Kendrick Lamar
- Which country star sang with Taylor Swift on “Highway Don’t Care”? Answer: Tim McGraw
- Who joined Taylor Swift in the song “The Last Time”? Answer: Gary Lightbody
- Which artist featured in Taylor’s track “Two Is Better Than One”? Answer: Boys Like Girls
- Who collaborated with Taylor Swift on the song “Babe”? Answer: Sugarland
- Taylor Swift and Brendon Urie teamed up for what colorful anthem? Answer: ME!
- Taylor and Haim collaborated on which murder mystery-themed track? Answer: No Body, No Crime
- Taylor Swift and Phoebe Bridgers worked together on what track from “Red (Taylor’s Version)”? Answer: Nothing New
- What song did Taylor Swift co-write with Zayn Malik? Answer: I Don’t Wanna Live Forever
- Who worked with Taylor Swift on “Coney Island”? Answer: The National
- Which legendary songwriter joined Taylor Swift on the song “Renegade”? Answer: Aaron Dessner
- Who is Taylor’s frequent collaborator in her indie era? Answer: Jack Antonoff
- Which Bon Iver member sang with Taylor Swift on “Exile”? Answer: Justin Vernon
- Taylor Swift teamed up with which pop star for a remix of “Lover”? Answer: Shawn Mendes
- Which rapper was Taylor Swift rumored to collaborate with during the “1989” era? Answer: Drake (though no official release)
- Who did Taylor collaborate with on the song “Run”? Answer: Ed Sheeran
- What artist is both a friend and co-writer of Taylor Swift’s “You All Over Me”? Answer: Maren Morris
- What Taylor Swift collaboration featured in the “Fifty Shades Darker” soundtrack? Answer: I Don’t Wanna Live Forever (with Zayn)
- Which indie folk artist produced much of “Folklore” and “Evermore”? Answer: Aaron Dessner
Taylor Swift Easter Eggs & Clues Riddles
- What are Taylor Swift’s secret hints to fans often called? Answer: Easter eggs
- What number does Taylor hide in videos and lyrics as a clue? Answer: 13
- Which music video features a painting that hints at the “Lover” era? Answer: ME!
- Taylor Swift hinted at the “Red (Taylor’s Version)” release in which video? Answer: Wildest Dreams (Taylor’s Version)
- In which video did fans first notice the clock pointing to midnight? Answer: Bejeweled
- What accessory in “You Belong With Me” video foreshadowed “Speak Now”? Answer: Purple dress
- What bakery-themed detail teased “No Body, No Crime”? Answer: Haim sisters holding baked goods in a teaser photo
- What object appears in the “Willow” video hinting at “Evermore”? Answer: The golden string
- What animal has symbolized Taylor Swift since the “Reputation” era? Answer: Snake
- What word appeared in capital letters throughout a lyric booklet to hint at a future album? Answer: Speak Now (in the Fearless booklet)
- What era used butterflies as a hidden clue? Answer: Lover era
- Which album was teased with “TS7” clues? Answer: Lover
- What candy appeared in the “ME!” video representing pastel themes? Answer: Cotton candy
- What hidden item in “Look What You Made Me Do” represents past selves? Answer: Coffins and outfits
- What animal appears repeatedly in the “Lover” house video scenes? Answer: Cats
- What famous bridge was subtly referenced in “London Boy”? Answer: Tower Bridge
- What recurring imagery ties “Cardigan,” “August,” and “Betty” together? Answer: High school love triangle
- What object in “All Too Well: The Short Film” connects to the scarf mystery? Answer: Red scarf
- What color scheme was used to foreshadow “Midnights”? Answer: Deep blues and purples
- Which music video ends with a clock striking twelve? Answer: Bejeweled
Taylor Swift Mythology & Folklore-Inspired Riddles
- What song from “Folklore” is inspired by a fictional story of infidelity? Answer: Betty
- Which song from “Evermore” deals with a tragic ghost story? Answer: Tolerate It
- Which track involves a woman taking revenge after being wronged? Answer: No Body, No Crime
- What song narrates the tale of a woman who stole another’s house? Answer: The Last Great American Dynasty
- Which “Folklore” song is written from a male perspective? Answer: Illicit Affairs
- In what song does Taylor use the metaphor of a “mirrorball”? Answer: Mirrorball
- What song compares a relationship to the season of summer and ends badly? Answer: Cruel Summer
- What character appears in the trilogy of “Betty,” “August,” and “Cardigan”? Answer: James
- What kind of tree is featured in the “Willow” music video setting? Answer: Willow tree
- What song title is also a common word for a fairytale object? Answer: Cardigan
- Which song evokes an eerie, almost magical winter setting? Answer: Evermore
- What “Folklore” track alludes to betrayal using historical references? Answer: Mad Woman
- Which Evermore song uses courtroom metaphors? Answer: Ivy
- What character-driven ballad reflects a widow’s strange life story? Answer: The Last Great American Dynasty
- What track presents Taylor as a spectral storyteller? Answer: Epiphany
- Which mythological theme appears in “Gold Rush”? Answer: Desire and envy
- Which dreamy ballad in “Folklore” is about a crush from afar? Answer: Invisible String
- What Evermore song features subtle references to funeral symbolism? Answer: Champagne Problems
- Which “Folklore” song’s title is also an item of clothing? Answer: Cardigan
- What song ends with the imagery of fading lights and isolation? Answer: Exile
Final Thought
From playful riddles about lyrics to clever puzzles about albums, awards, and tours this list of Taylor Swift riddles offers something fun for every fan. Whether you’re solving these with your besties or using them to test your Swiftie IQ, they make for an entertaining way to engage with one of music’s most iconic storytellers.
