150 Taylor Swift Riddles Every Devoted Fan Should Know

Are you a true Taylor Swift fan looking to test your knowledge and have some fun? Taylor Swift Riddles are the perfect way to engage with her music, lyrics, and iconic moments. Whether you’re hosting a Swift-themed party, enjoying a quiet night in, or simply want to challenge yourself, these 150 riddles cater to every level of fandom. From easy questions that every casual listener can enjoy to hard puzzles reserved for the most devoted Swifties, this collection ensures there’s something for everyone.

Fans often struggle to recall specific lyrics, album details, or behind-the-scenes stories, making these riddles not only entertaining but also a great way to deepen your appreciation for Taylor’s artistry. Dive into interactive challenges, solve tricky puzzles, and celebrate your love for Taylor Swift with riddles that capture the essence of her incredible career. Get ready to prove you’re the ultimate Swiftie!

Swift Puzzles for the Swift-Minded

1. Riddle: I was released in 2008, featuring a song about a boy who wouldn’t treat me right. What album am I? Answer: Fearless
2. Riddle: This song narrates a teenage love story set against a backdrop of “wildest dreams.” What is the song’s title? Answer: “Love Story”
3. Riddle: Which Taylor Swift album includes the hit song “Blank Space”? Answer: 1989
4. Riddle: I am Taylor’s debut single, which talks about moving on from a broken relationship. What am I? Answer: “Tim McGraw”
5. Riddle: This song features a collaboration with Ed Sheeran and discusses friendship and fame. What is it called? Answer: “Everything Has Changed”
6. Riddle: Which album did Taylor release after Reputation? Answer: Lover
7. Riddle: In which song does Taylor mention, “The lights are so bright, but they never blind me”? Answer: “Clean”
8. Riddle: This song’s music video features Taylor in a prison setting. What is the song? Answer: “Look What You Made Me Do”
9. Riddle: What is the name of the song where Taylor sings about a secret relationship in the “Gorgeous” song? Answer: “Gorgeous”
10. Riddle: Which album includes the track “The Archer”? Answer: Lover
11. Riddle: In which song does Taylor reference the “Clock of Ages”? Answer: “All Too Well”
12. Riddle: What song starts with the lyrics “I remember when we broke up the first time”? Answer: “We Are Never Ever Getting Back Together”
13. Riddle: Which Taylor Swift song features a cameo by Taylor herself in the music video alongside a snake? Answer: “Look What You Made Me Do”
14. Riddle: This song was inspired by Taylor’s feud with Kanye West and Kim Kardashian. What is it? Answer: “Look What You Made Me Do”
15. Riddle: Which song from the Folklore album tells a story from the perspective of a housekeeper? Answer: “The Last Great American Dynasty”
16. Riddle: What is the name of Taylor’s song that references the zodiac sign Pisces? Answer: “Delicate”
17. Riddle: Which track from Evermore features a collaboration with The National? Answer: “Coney Island”
18. Riddle: In which song does Taylor mention “Battered by Storms”? Answer: “Safe & Sound”
19. Riddle: What song includes the lyric “Band-aids don’t fix bullet holes”? Answer: “Bad Blood”
20. Riddle: Which Taylor Swift song features a reference to London Bridge? Answer: “London Boy”
21. Riddle: What is the title of the song where Taylor sings about “sparks fly”? Answer: “Sparks Fly”
22. Riddle: Which song from Red features the lyric “Loving him was red”? Answer: “Red”
23. Riddle: In which song does Taylor use the metaphor of a “mirrorball”? Answer: “Mirrorball”
24. Riddle: Which Taylor Swift song features the line “I’m a nightmare dressed like a daydream”? Answer: “Blank Space”
25. Riddle: What is the name of the song where Taylor sings about driving down a stormy street? Answer: “Clean”

Easy Taylor Swift Riddles

1. Riddle: What was Taylor Swift’s first number-one single on the Billboard Hot 100? Answer: “Our Song”
2. Riddle: Which song includes the lyric “You belong with me”? Answer: “You Belong with Me”
3. Riddle: What is the title of Taylor’s song that shares its name with a famous apple variety? Answer: “Apple.” (Note: This is a trick question; Taylor doesn’t have a song named “Apple.” Possible correction: “None. Taylor Swift doesn’t have a song named ‘Apple.'” Alternatively, change the riddle.)
4. Riddle: Which Taylor Swift song features the line “Shake it off”? Answer: “Shake It Off”
5. Riddle: What is the name of Taylor’s song that encourages letting go of negativity? Answer: “Shake It Off”
6. Riddle: Which song from 1989 has a music video featuring Taylor as a cat? Answer: “Blank Space”
7. Riddle: In which song does Taylor sing about a “King of my heart”? Answer: “King of My Heart”
8. Riddle: What is the title of Taylor’s song that talks about being fearless in love? Answer: “Fearless”
9. Riddle: Which song includes the lyric “Darling, I’m a nightmare dressed like a daydream”? Answer: “Blank Space”
10. Riddle: What is the name of the song where Taylor reflects on her past relationship in 10 minutes? Answer: “All Too Well”
11. Riddle: Which Taylor Swift song has the chorus “I don’t wanna touch you, I don’t wanna be just another ex-love”? Answer: “Gorgeous”
12. Riddle: What is the title of Taylor’s song that shares its name with a Disney princess? Answer: “Enchanted”
13. Riddle: Which song features Taylor singing about a “beautiful disaster”? Answer: “State of Grace”
14. Riddle: What is the name of the song where Taylor sings about a “secret society”? Answer: “Secret Society”
15. Riddle: Which song from Reputation talks about fame and its challenges? Answer: “Ready For It?”
16. Riddle: What is the title of Taylor’s song that includes the line “I’m shining like fireworks over your sad, empty town”? Answer: “Ours”
17. Riddle: Which song features Taylor singing about being fearless and taking risks in love? Answer: “Fearless”
18. Riddle: What is the name of the song where Taylor sings about “dancing around the kitchen in the refrigerator light”? Answer: “Begin Again”
19. Riddle: Which Taylor Swift song features a reference to “Holy Ground”? Answer: “Holy Ground”
20. Riddle: What is the title of the song where Taylor sings, “I remember it all too well”? Answer: “All Too Well”
21. Riddle: Which song includes the lyric “Cause darling I’m a nightmare dressed like a daydream”? Answer: “Blank Space”
22. Riddle: What is the name of Taylor’s song that encourages moving on and not looking back? Answer: “Shake It Off”
23. Riddle: Which song from Lover features pastel colors and a whimsical music video? Answer: “Lover”
24. Riddle: What is the title of Taylor’s song that shares its name with a famous city in Pennsylvania? Answer: “Welcome to New York”
25. Riddle: Which song features Taylor singing about being fearless and standing tall? Answer: “Fearless”

Hard Taylor Swift Riddles

1. Riddle: In which song does Taylor Swift reference “the man” and discuss gender double standards? Answer: “The Man”
2. Riddle: Which track from Folklore is a fictional story about a maid named Virginia? Answer: “The Last Great American Dynasty”
3. Riddle: What is the name of the song where Taylor collaborates with Bon Iver? Answer: “Exile”
4. Riddle: In which song does Taylor use the metaphor of a “mirrorball” to describe herself? Answer: “Mirrorball”
5. Riddle: Which song from Evermore tells a story of a love triangle set in the 1980s? Answer: “Champagne Problems”
6. Riddle: What is the title of the song where Taylor explores the theme of immortality in a relationship? Answer: “Evermore”
7. Riddle: In which song does Taylor Swift mention “gold chains and swimming pools”? Answer: “Style”
8. Riddle: Which track from Reputation includes a spoken word intro addressing media perception? Answer: “Ready For It?”
9. Riddle: What is the name of the song where Taylor references the “cool kids” and social cliques? Answer: “You Need to Calm Down”
10. Riddle: In which song does Taylor Swift use the phrase “tied together with a smile”? Answer: “Invisible String”
11. Riddle: What is the title of the song where Taylor sings about being “the princess and the pawn”? Answer: “The Archer”
12. Riddle: Which song from Folklore features Taylor narrating from the perspective of a teenage boy named James? Answer: “Betty”
13. Riddle: What is the name of the song where Taylor Swift discusses her relationship with a “signer”? Answer: “You Are In Love”
14. Riddle: In which song does Taylor reference the “Grand Canyon” as a metaphor for a relationship? Answer: “The Lakes”
15. Riddle: What is the title of the song where Taylor reflects on her “seven” years with an ex-lover? Answer: “Seven”
16. Riddle: Which track from Evermore features themes of longing and nostalgia for a past love? Answer: “Willow”
17. Riddle: In which song does Taylor Swift sing about “cruel summer” and intense emotions? Answer: “Cruel Summer”
18. Riddle: What is the name of the song where Taylor collaborates with Aaron Dessner? Answer: “Willow”
19. Riddle: Which song from Folklore tells a story of love lost and regret in a quiet town? Answer: “The Story of Us”
20. Riddle: What is the title of the song where Taylor sings about “evermore, and forevermore”? Answer: “Evermore”
21. Riddle: In which song does Taylor Swift use the imagery of “golden hours” and “silver skies”? Answer: “Daylight”
22. Riddle: What is the name of the song where Taylor reflects on her past self and growth? Answer: “The 1”
23. Riddle: Which track from Reputation delves into themes of revenge and reclaiming power? Answer: “Look What You Made Me Do”
24. Riddle: In which song does Taylor mention “Tangled Up with You” as part of a lyric? Answer: “Begin Again”
25. Riddle: What is the title of the song where Taylor sings about “paper rings” and commitment? Answer: “Paper Rings”

Interactive Taylor Swift Riddles

1. Riddle: I am a song where you can clap your hands along to the upbeat rhythm. Which song am I? Answer: “Shake It Off”
2. Riddle: Guess the song: I talk about a love that’s like a rollercoaster, full of ups and downs. Answer: “Mine”
3. Riddle: I’m a song where Taylor invites you to dance with her under the city lights. What song am I? Answer: “Style”
4. Riddle: Identify the song: I describe a relationship that feels both magical and mysterious, like a fairy tale. Answer: “Enchanted”
5. Riddle: I’m a song that encourages you to forget the haters and enjoy life. Which song am I? Answer: “Shake It Off”
6. Riddle: Guess the song: I reminisce about a past relationship with both fondness and sorrow. Answer: “All Too Well”
7. Riddle: I am a song where Taylor sings about holding onto hope during tough times. What am I? Answer: “Clean”
8. Riddle: Identify the song: I feature a catchy chorus that you can’t help but sing along to. Answer: “Love Story”
9. Riddle: I’m a song where Taylor describes a secret romance hidden from the world. Which song am I? Answer: “Invisible String”
10. Riddle: Guess the song: I talk about the excitement and nervousness of a new love. Answer: “Begin Again”
11. Riddle: I am a song where you can clap your hands and stomp your feet to the beat. What am I? Answer: “Shake It Off”
12. Riddle: Identify the song: I use vivid imagery to describe a dreamy night with a loved one. Answer: “Wildest Dreams”
13. Riddle: I’m a song where Taylor sings about overcoming heartbreak and finding strength. Which song am I? Answer: “The Archer”
14. Riddle: Guess the song: I blend pop and country elements to tell a heartfelt story. Answer: “Teardrops on My Guitar”
15. Riddle: I am a song where you can dance freely without worrying about judgment. What am I? Answer: “Shake It Off”
16. Riddle: Identify the song: I explore the complexities of fame and personal identity. Answer: “Look What You Made Me Do”
17. Riddle: I’m a song where Taylor expresses longing for a simpler time. Which song am I? Answer: “Tim McGraw”
18. Riddle: Guess the song: I talk about a love that feels like it’s written in the stars. Answer: “Starlight”
19. Riddle: I am a song where you can sing along to the empowering chorus. What am I? Answer: “Shake It Off”
20. Riddle: Identify the song: I tell a story of two people reconnecting after years apart. Answer: “Back to December.”
21. Riddle: I’m a song where Taylor sings about finding peace and clarity. Which song am I? Answer: “Daylight”
22. Riddle: Guess the song: I feature a catchy hook about dancing through the night. Answer: “Shake It Off”
23. Riddle: I am a song where you can clap your hands to celebrate love. What am I? Answer: “Love Story”
24. Riddle: Identify the song: I depict the bittersweet feeling of a love that’s ending. Answer: “Sad Beautiful Tragic”
25. Riddle: I’m a song where Taylor encourages embracing your true self. Which song am I? – Answer: “You Need to Calm Down”

Taylor Swift’s Song Riddles for Kids

1. Riddle: I am a fun song where Taylor talks about dancing and having a good time. What am I? Answer: “Shake It Off”
2. Riddle: Which song tells a sweet story about a princess and her love? Answer: “Love Story”
3. Riddle: I am a song where Taylor sings about playing in the rain with friends. What am I? Answer: “Fearless”
4. Riddle: What is the name of the song where Taylor sings about cupcakes and candy? Answer: “Welcome to New York”
5. Riddle: I am a cheerful song where Taylor encourages kids to be themselves. What am I? Answer: “Shake It Off”
6. Riddle: Which song talks about friendship and being there for each other? Answer: “You Belong with Me”
7. Riddle: I am a song where Taylor sings about having adventures and exploring new places. What am I? Answer: “Wildest Dreams”
8. Riddle: What is the title of the song where Taylor sings about riding bikes and having fun? Answer: “22”
9. Riddle: I am a song that makes you want to jump and dance along. What am I? Answer: “Shake It Off”
10. Riddle: Which song describes a magical night under the stars? Answer: “Enchanted”
11. Riddle: I am a song where Taylor talks about playing hide and seek with love. What am I? Answer: “Everything Has Changed”
12. Riddle: What is the name of the song where Taylor sings about building castles in the sand? Answer: “Invisible String”
13. Riddle: I am a happy song where Taylor sings about sunshine and smiles. What am I? Answer: “Welcome to New York”
14. Riddle: Which song encourages kids to dance like nobody’s watching? Answer: “Shake It Off”
15. Riddle: I am a song where Taylor sings about flying kites on a windy day. What am I? Answer: “The Story of Us”
16. Riddle: What is the title of the song where Taylor sings about a playground and swinging? Answer: “Begin Again”
17. Riddle: I am a song that talks about magical moments and fairy tales. What am I? Answer: “Love Story”
18. Riddle: Which song makes you want to twirl and spin around happily? Answer: “Shake It Off”
19. Riddle: I am a song where Taylor sings about colorful balloons and joy. What am I? Answer: “22”
20. Riddle: What is the name of the song where Taylor sings about singing in the rain? Answer: “Fearless”
21. Riddle: I am a cheerful song that talks about summer days and sunshine. What am I? Answer: “Welcome to New York”
22. Riddle: Which song encourages kids to clap their hands and stomp their feet? Answer: “Shake It Off”
23. Riddle: I am a song where Taylor sings about making wishes on a shooting star. What am I? Answer: “Sparks Fly”
24. Riddle: What is the title of the song where Taylor sings about ice cream and fun? Answer: “Me!”
25. Riddle: I am a song that makes you feel brave and unstoppable. What am I? Answer: “Fearless”

Tricky Taylor Swift Riddles for Adults

1. Riddle: In which song does Taylor Swift reference the “grandest scene” and a metaphorical cityscape? Answer: “Welcome to New York”
2. Riddle: What is the name of the song where Taylor uses the phrase “mad woman” to describe herself? Answer: “mad woman”
3. Riddle: In which track does Taylor Swift discuss the concept of “invisible strings” tying her to someone? Answer: “Invisible String”
4. Riddle: Which song from Folklore explores the theme of memory and storytelling through a snowy setting? Answer: “The 1”
5. Riddle: What is the title of the song where Taylor reflects on the duality of her public and private personas? Answer: “The Archer”
6. Riddle: In which song does Taylor Swift mention “sword fights” and personal battles? Answer: “The Man”
7. Riddle: What is the name of the song where Taylor sings about a relationship that feels like a game of chess? Answer: “Getaway Car”
8. Riddle: Which track from Reputation delves into themes of vengeance and rebirth? Answer: “Look What You Made Me Do”
9. Riddle: In which song does Taylor Swift use the metaphor of a “mirrorball” to represent herself? Answer: “Mirrorball”
10. Riddle: What is the title of the song where Taylor discusses the weight of expectations and fame? Answer: “Blank Space”
11. Riddle: Which song from Evermore features a narrative about a haunted house and lingering memories? Answer: “Champagne Problems”
12. Riddle: In which track does Taylor Swift explore the idea of destiny and preordained connections? Answer: “Invisible String”
13. Riddle: What is the name of the song where Taylor sings about navigating a toxic relationship with grace? Answer: “Delicate”
14. Riddle: Which song from Folklore tells the story of a teenage boy named James and his feelings? Answer: “Betty”
15. Riddle: In which song does Taylor Swift reflect on her past self and personal growth using the imagery of autumn? Answer: “All Too Well”
16. Riddle: What is the title of the song where Taylor sings about the facade she presents to the world? Answer: “The Lakes”
17. Riddle: Which track delves into the complexities of a relationship that’s both beautiful and painful? Answer: “State of grace”
18. Riddle: In which song does Taylor Swift mention “Green Eyes” and Lost Love? Answer: “Everything Has Changed”
19. Riddle: What is the name of the song where Taylor explores themes of regret and longing in a relationship? Answer: “Last Kiss”
20. Riddle: Which song from Reputation includes a narrative about a tumultuous relationship and personal reinvention? Answer: “Ready For It?”
21. Riddle: In which track does Taylor Swift use the metaphor of a “peaceful place” to describe her ideal state of mind? Answer: “Peace”
22. Riddle: What is the title of the song where Taylor sings about feeling like she’s “locked out” of someone’s life? Answer: “This Is Why We Can’t Have Nice Things”
23. Riddle: Which song from Folklore features a collaboration with Aaron Dessner and tells a haunting story? Answer: “Exile”
24. Riddle: In which song does Taylor Swift discuss the concept of time standing still in a relationship? Answer: “Timeless”
25. Riddle: What is the name of the song where Taylor explores the idea of fate and intertwined lives through subtle references? Answer: “Invisible String”

Final Thoughts

Embarking on these Taylor Swift Riddles has been an exciting journey through her musical genius and lyrical prowess. Whether you tackled the easy puzzles or braved the tricky challenges, each riddle offered a unique way to connect with Taylor’s diverse discography and memorable moments.

If you find yourself stumped or triumphant, remember that these riddles are not just tests of knowledge but celebrations of being a devoted fan. Don’t keep the fun to yourself! Share these riddles with fellow Swifties, challenge your friends, and keep the spirit of Taylor’s music alive through playful discovery. Dive back in any time to refresh your memory or uncover new insights, and continue to revel in the magic that makes Taylor Swift a beloved icon. Happy puzzling!