Got a Long List of Ex Lovers
What Are My Words Worth
Put On Your Records And Regret Me
Bridges Burn, I Never Learn
I Go On Too Many Dates
100

Swift attended SuperBowl LVIII to cheer on this boyfriend as he played for the Kansas City Chiefs

Who is Travis Kelce?

100

This song contains the following lyric:

"Memorizing him was as easy as knowing all the words to your old favorite song"

What is "Red"?

100

As of 2023, this tour holds the Guinness World Record for Highest-Grossing Music Tour of all time

What is the Eras Tour?

100

This song contains the following bridge:

"I’m drunk in the back of the car
And I cried like a baby comin’ home from the bar"

What is "Cruel Summer"?

100

On this date, Taylor Alison Swift was born in West Reading, Pennsylvania 

What is December 13, 1989?

200

Swift claims this ex broke up with her over a 27 second phone call

Who is Joe Jonas?

200

This song contains the following lyric:

"Why they lost their minds and fought the wars
And why I've spent my whole life trying to put it into words"

What is "You Are in Love"?

200

This album holds the record for the most weeks at number one for a female country album

What is "Fearless"?

200

This song contains the following bridge:

"Remember when you hit the brakes too soon?
Twenty stitches in the hospital room"

What is "Out of the Woods"?

200

On this date, Swift's 11th album, Tortured Poets Department, was released.

What is April 19, 2024?

300

Swift wrote "Back to December" about this ex-boyfriend

Who is Taylor Lautner?

300

This song contains the following lyric:

"Until I see you again
These are the words I held back as I was leaving too soon"

What is "Enchanted"?

300

Swift set a new record in 2024 when she became the first artist in history to win four of these awards

What is the Grammy for Album of the Year?

300

This song contains the following bridge:

"Well, maybe we got lost in translation, maybe I asked for too much
But maybe this thing was a masterpiece ’til you tore it all up"

What is "All Too Well"?

300

On this date, The Eras Tour kicked off in Glendale, Arizona.

What is March 17, 2023?

400

Swift became Instagram official with this ex when she posted a photo of them riding an inflatable duck

Who is Calvin Harris?

400

This song contains the following lyric:

"Long handwritten notes, deep in your pocket
Words, how little they mean when you're a little too late"

What is "Sad, Beautiful, Tragic"?

400

After Swift released this single in 2006, she became the youngest artist in history to have written and performed a No. 1 song on the Hot Country Songs chart

What is "Our Song"?

400

This song contains the following bridge:

"Back when we were still changin’ for the better
Wanting was enough
For me, it was enough"

What is "August"?

400

On this date, Swift released her first pop album, 1989. 

What is October 27, 2014?

500

Swift briefly dated this grandson of a former U.S. president

Who is Conor Kennedy?

500

This song contains the following lyric:

"So just walk away, ain't no use defending
words that you will never say"

What is "Cold as You"?

500

Swift achieved this record when "Is It Over Now?" debuted at No. 1 on the Hot 100

What is the only woman to replace herself at no. 1? (Dethroned "Cruel Summer")

500

This song contains the following bridge:

"You think I didn't see there were flashing lights? At least I had the decency to keep my nights out of sight"

What is "Is it Over Now? (From the Vault)" ?

500

On this date, Swift was interrupted by Kanye West during her acceptance speech for Best Female Video at the MTV Video Music Awards

What is September 13, 2009?

600

He played the love interest of Swift in her 2008 music video for "You Belong With Me", later stating they dated "for a little bit" before it fizzled out.

Who is Lucas Till?

600

This song contains the following lyric:

"And you watched me go
And I knew my words were hard to hear
And harder to ever take back"

What is "That's When (From the Vault)"?

600

Swift has won the most of this award in history, holding 40 awards. Swift surpassed Michael Jackson, who holds 26 awards, and Whitney Houston, who holds 22.

What are the American Music Awards?

600

This song contains the following bridge:

"So I'll walk out of here tonight
Try to go on with my life
And you can say we're still friends"

What is "Don't You (From the Vault)"?

600

On this date, Swift released her self-titled debut album, a collection of country-pop tunes the singer wrote during her freshman year of high school.

What is October 24, 2006?