72 Challenging Taylor Swift Trivia Questions And Answers

2023 was truly the year of Taylor Swift. She continues to captivate fans across the globe with her sold-out Eras Tour, and re-releases of her beloved studio albums. Taylor has amassed a following of loyal ‘Swifties,’ an army of fans who know the ins and outs of her music, her style, and even her personal life.

But to give yourself this honorable title, you must prove how big of a ‘Swiftie’ you really are! Answer our trivia questions, and see whether you’re a mastermind, or simply the foolish one.

Are you ready for it?

How to Plan a Taylor Swift Party

Planning a Taylor Swift-themed party can be a fun and exciting experience for fans of all ages. From decor and costumes to food and activities, there are endless possibilities to make this party a memorable celebration of Taylor Swift’s music and career. Here are some steps to help you plan the perfect Taylor Swift-themed party:

1. Set the Date and Location:
   Choose a date that works best for you and your guests.
   Decide on a location, whether it’s your home, a rented venue, or even an outdoor space.
2. Create Invitations:
   Design custom invitations inspired by Taylor Swift’s album covers or concert themes.
   Include details such as date, time, location, and any dress code requirements. Many fans like to dress up as different ‘eras’ from Taylor’s career, and you can find plenty of outfit inspo and Pinterest and TikTok.
   Incorporate Taylor Swift lyrics or song titles into the invitation for an extra touch.
3. Decorations:
   Incorporate Taylor Swift’s signature colors, such as red, white, and gold, into your decor.
   Display Taylor Swift posters, album covers, and iconic photos throughout the party area.
   Set up a photo booth area with props like oversized sunglasses, cowboy hats, and Taylor Swift-inspired outfits.
   Hang fairy lights or light-up signs with Taylor Swift lyrics or quotes.
   For an extra touch, create a stage backdrop using her album covers or memorable images from her music videos.
4. Dress Code:
   Encourage guests to dress up as their favorite Taylor Swift era, from country-inspired outfits and cowboy boots, to folklore and evermore cardigans and braids.
   Provide a crown or tiara for guests to wear to represent Taylor’s “Reputation” era.
5. Food and Drinks:
    Create a themed menu inspired by Taylor Swift’s favorite foods or song references.
    Serve “Love Story” Caramel Apple Pie, “Bad Blood” infused cocktails or mocktails. You could even ask guests to create their own ‘snack boards’ based on a different Taylor Swift era.
    Decorate cupcakes or cookies with Taylor Swift-inspired designs.
6. Music Playlist:
   No party is complete without music, and what better excuse to blast Taylor anthemes all night than a Swiftie party! Create a customized playlist featuring Taylor Swift’s greatest hits, from her country classics to her pop anthems. Streaming services, such as Spotify, also have plenty of Taylor playlists for you to choose from.
   Include fan favorites like “Love Story,” “You Belong with Me,” “Blank Space,” and “Shake It Off.”
   Add some lesser-known tracks to challenge fans during the trivia section. You could even include an ‘Intros’ round, where people have to guess the song from the first few seconds.
7. Activities:
   Taylor Swift Trivia: Below, we’ve listed a range of Taylor Swift trivia questions for you to challenge your friends and family with, including easy questions for the casual fans, and more difficult trivia for the hardcore Swifties. Divide guests into teams and offer small prizes for the winning team!
   Karaoke: Karaoke is always a fun time, so set up a karaoke machine or create a playlist of Taylor Swift songs for guests to show off their singing skills to!
   Dance-off: Organize a dance-off where guests can showcase their best Taylor Swift-inspired dance moves. Include songs with iconic music videos, such as “Shake It Off” and “Delicate.”
8. Party Favors:
   For the finishing touch to your Swiftie Extravaganza, create personalized party favors, such as custom-made Taylor Swift-themed keychains, bracelets, or mini albums.
   Include a handwritten note from Taylor Swift (or a replica) thanking guests for attending the party.

Whether you’re a long-time Swiftie or introducing her music to new fans, a Taylor Swift-themed party is a great way to celebrate her talent and share a memorable experience with friends and loved ones.

We’ve compiled a range of Taylor Swift trivia questions below, so you can have the ultimate quiz with friends and family! Our trivia is organized into three sections, depending on how much of a Swiftie you and your friends are:

• Easy (Trivia for Newbie Swifties and Casual Fans)
• Intermediate (Trivia for Big Taylor Swift Fans)
• Hard (Trivia for Hardcore Swifties)

Easy Taylor Swift Trivia

1. In which state was Taylor Swift born?
   Show answer
   Pennsylvania.
2. What is the name of Taylor’s loyal fanbase?
   Show answer
   Swifties.
3. What was the first single from Taylor Swift’s debut album?
   Show answer
   “Tim McGraw.”
4. Which famous actor starred alongside Taylor Swift in her music video for “Bad Blood”?
   Show answer
   Selena Gomez.
5. True or false: Taylor Swift won the Grammy Award for Album of the Year multiple times.
   Show answer
   True.
6. What is the name of Taylor Swift’s sixth concert tour, and her second stadium-only tour, which recently became the most popular concert tour of all time?
   Show answer
   The Eras Tour.
7. What is the name of Taylor Swift’s most recent studio album, released in 2022?
   Show answer
   “Midnights.”
8. Which Taylor Swift song became her first number-one hit on the Billboard Hot 100 chart?
   Show answer
   “Love Story.”
9. What is the full title of Taylor Swift’s second studio album?
   Show answer
   “Fearless.”
10. Which Taylor Swift album featured the hit singles “Bad Blood” and “Wildest Dreams”?
    Show answer
    “1989.”
11. Which song from Taylor Swift’s album “Speak Now” was rumored to be about her relationship with actor Taylor Lautner?
    Show answer
    “Back to December.”
12. What is the name of Taylor Swift’s debut album?
    Show answer
    “Taylor Swift.”
13. Which NFL football player is Taylor Swift dating as of early 2024?
    Show answer
    Travis Kelce.
14. Which popular Taylor Swift song is believed to be about former One Direction member, Harry Styles?
    Show answer
    Style..
15. Taylor won her first Grammy at what age?
    Show answer
    20.

Intermediate Taylor Swift Trivia

1. Which Taylor Swift song became the longest-running #1 hit on the Billboard Hot 100 chart?
   Show answer
   “Shake It Off.”
2. Which album notably marked Taylor Swift’s transition from country to pop?
   Show answer
   “1989.”
3. What was the name of Taylor Swift’s first official concert tour?
   Show answer
   “Fearless.”
4. Which fashion magazine featured Taylor Swift on its cover for the first time in 2019?
   Show answer
   Vogue.
5. What is the name of Taylor Swift’s documentary film released on Netflix in 2020?
   Show answer
   “Miss Americana.”
6. Which streaming platform exclusively featured Taylor Swift’s album “Reputation” upon its release?
   Show answer
   Apple Music.
7. Which song from Taylor Swift’s album “Speak Now” is rumored to be inspired by her feud with fellow musician John Mayer?
   Show answer
   “Dear John.”
8. True or false: Taylor Swift’s middle name is Alison.
   Show answer
   True.
9. Taylor met actor Taylor Lautner during the filming of which movie?
   Show answer
   Valentine’s Day.
10. Name the collaboration between Taylor Swift and Brendon Urie of Panic! At The Disco released in 2019.
    Show answer
    “ME!”
11. Taylor is named after which singer-songwriter?
    Show answer
    James Taylor.
12. Which movie features two Taylor written songs?
    Show answer
    “Hannah Montana: The Movie.”
13. How many studio albums has Taylor Swift released as of 2024?
    Show answer
    Ten.
14. Which song from Taylor Swift’s album “1989” became the first ever to debut at #1 on the Hot 100 chart?
    Show answer
    “Shake It Off.”
15. In which year did Taylor Swift release her debut album?
    Show answer
    2006.
16. Which song did Taylor write to perform at her high school talent show, which would later go on to be a huge hit?
    Show answer
    “Our Song.”
17. Which rock band did Taylor Swift famously join on stage to perform their hit song “Livin’ on a Prayer”?
    Show answer
    Bon Jovi.
18. Which song from Taylor Swift’s album “Red” was rumored to be about her brief relationship with actor Jake Gyllenhaal?
    Show answer
    “All Too Well.”
19. The Taylor Swift album “Speak Now” was released in what year?
    Show answer
    2010.
20. True or False: Taylor Swift won an Oscar for ‘Best Original Song.’
    Show answer
    False.
21. In 2014, which streaming service did Taylor remove her music from?
    Show answer
    Spotify.
22. Taylor Swift has re-recorded her original music to reclaim it under her label. In these re-recorded albums, she releases previously unheard songs as a special treat for fans. What are these new songs referred to as?
    Show answer
    ‘From the Vault’ songs.
23. Which song by Taylor Swift holds the record for the longest-running number-one hit on the Billboard Hot 100 chart (16 weeks)?
    Show answer
    “Blank Space.”
24. Which album did Taylor Swift win Album of the Year for at the Grammy Awards in 2021?
    Show answer
    “Folklore.”
25. In what year did Taylor Swift release her hit single “Shake It Off”?
    Show answer
    2014.
26. How many Grammys has Taylor Swift won in total (up to 2023)?
    Show answer
    12.
27. In 2009, Kanye West interrupted Taylor Swift’s speech at which awards show?
    Show answer
    MTV Video Music Awards.
28. What is Taylor Swift’s lucky number?
    Show answer
    13
29. Taylor would go on to write a Christmas hit based on her life growing up. But what was so special about where she grew up?
    Show answer
    She grew up on a Pennsylvania Christmas Tree Farm.
30. True or False: Taylor holds the Guinness World Record for the most U.S. Number 1 albums by a female artist.
    Show answer
    True.
31. Which song earned Taylor an award for Best Female Video at the 2009 MTV VMAs?
    Show answer
    “You Belong With Me.”

Hard Taylor Swift Trivia

1. True or False: Taylor Swift is the youngest artist ever to win Album of the Year at the Grammy Awards.
   Show answer
   True.
2. Which Taylor Swift song mentions “friendship bracelets,” based on a tradition that her fans exchange bracelets at her concerts?
   Show answer
   “You’re On Your Own, Kid.”
3. As a special surprise for two fans, Taylor Swift sang which song at their engagement party?
   Show answer
   “King of My Heart.”
4. Taylor made a big donation of $50,000 in 2015 to which organization?
   Show answer
   The Seattle Symphony Orchestra.
5. Which singer-songwriter has Taylor Swift collaborated with for the song “Both of Us”?
   Show answer
   B.o.B.
6. How many songs has Taylor released ‘From the Vault’ as of 2023?
   Show answer
   26 songs.
7. Taylor Swift wrote which 2016 dance anthem for another artist?
   Show answer
   “This Is What You Came For” by Calvin Harris feat. Rihanna.
8. Which actor appeared as Taylor Swift’s love interest in the music video for “You Belong with Me”?
   Show answer
   Lucas Till.
9. Taylor used to have a close relationship with which Victoria’s Secret model?
   Show answer
   Karlie Kloss.
10. Which female artist did Taylor Swift invite to join her on stage during her Red World Tour to perform “Brave”?
    Show answer
    Sara Bareilles.
11. Who is Taylor Swift’s best friend from high school, who she has even dedicated songs to?
    Show answer
    Abigail Anderson.
12. Which famous music producer discovered Taylor Swift at the age of 14?
    Show answer
    Scott Borchetta.
13. In the 2021 re-record of her best-selling album Red, Taylor released a 10-minute version of which popular song?
    Show answer
    “All Too Well.”
14. Which ‘From the Vault’ song is rumored to be about Harry Styles?
    Show answer
    “Now That We Don’t Talk.”
15. Which other famous singer did Taylor have a feud with, beginning in 2009?
    Show answer
    Katy Perry.
16. Which Taylor Swift song won the MTV Video Music Award for Video of the Year in 2015?
    Show answer
    “Bad Blood.”
17. Which hit crime TV show did Taylor Swift make her TV acting debut in?
    Show answer
    CSI: Crime Scene Investigation.
18. In which city was Taylor Swift born?
    Show answer
    Reading, Pennsylvania.
19. When is Taylor Swift’s birthday?
    Show answer
    December 13th 1989.
20. What is the title of the single Taylor Swift released in 2020 that features Bon Iver?
    Show answer
    “exile.”
21. True or False: Taylor Swift’s album “Speak Now” was entirely self-written.
    Show answer
    True.
22. What is the name of Taylor’s brother?
    Show answer
    Austin Swift.
23. What are Taylor’s cat’s names?
    Show answer
    Olivia Benson, Meredith Grey, and Benjamin Button.
24. During live shows, Taylor Swift fans famously chant during which “Reputation” song?
    Show answer
    Delicate.”
25. When she was 12 years old, who taught Taylor how to play guitar?
    Show answer
    Repairman and musician, Ronnie Cremer.
26. Taylor’s brother graduated from which college?
    Show answer
    Notre Dame.

Enjoy a Taylor Swift Party with Trivia Questions and Answers

Taylor Swift has undeniably left an incredible mark on the music industry, with her impressive songwriting, world-class performances, and powerful influence on fashion and culture. Her evolution from a young country singer to a worldwide pop superstar has been a fascinating journey to witness, connecting with millions of fans across the globe. 

Whether you aced the easy trivia questions or found the hard ones a true challenge, you can still be a Swiftie no matter what, and it’s clear that Taylor Swift’s impact on popular music can never be overstated. Her next album is sure to be a worldwide success, and if you’re able to see her on The Eras Tour before then, then you really are The Lucky One!

Eleanor Griffiths

Eleanor is a qualified English teacher and has received a Post Graduate Diploma in Education (PGDE), specializing in Secondary English, and holds a BA (Hons) in English Literature from Liverpool John Moores University. She is certified to teach English as a foreign language (TEFL) and has worked with students in the U.K. and South East Asia. She currently works as an English teacher in Vietnam, teaching students across a range of ages.

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