| Hint | Answer | % Correct |
|---|---|---|
| What song references Romeo and Juliet and was Swift's first top-ten Billboard hit? | Love Story | 91%
|
| What homage to a country singer was Taylor Swift's debut single? | Tim McGraw | 89%
|
| What song about a seasonal romance was on the album Lover in 2019 and became a smash hit in 2023 because of its prominence in the Eras tour? | Cruel Summer | 87%
|
| What was Midnight's lead single, a sardonic self-critique where Swift claims that her problems are actually caused by herself? | Anti-Hero | 86%
|
| What was Folklore's lead single, a poetic folk-rock ballad about a comfortable relationship between Betty and James? | Cardigan | 85%
|
| What song's music video, about a cheerleader and nerdy girl competing for a boy, won Music Video of the Year (much to Kanye's chagrin)? | You Belong with Me | 83%
|
| In what 2019 hit does Taylor Swift criticize internet trolls and homophobes, leading to it being called a "gay anthem"? | You Need to Calm Down | 82%
|
| What horribly catchy bubblegum smash hit calls out haters, players, and tabloids? | Shake it Off | 81%
|
| What Midnights "dream pop" love song, featuring Lana Del Rey, wasn't released as a single but still hit #4 on the Billboard Hot 100? | Snow on the Beach | 81%
|
| What was the third #1 hit from 1989 and was written as a diss track against Katy Perry? | Bad Blood | 80%
|
| What electropop bop was Reputation's lead single, hit #1 on the Billboard, and sampled 1991 hit "I'm Too Sexy"? | Look What You Made Me Do | 79%
|
| In what critically praised Billboard #1 hit does Taylor Swift poke fun at her dating history, saying her exes might call her insane? | Blank Space | 77%
|
| What song from 1989 refers without subtlety to Taylor Swift's romance with Harry Styles of One Direction fame? | Style | 75%
|
| What breakup song was Taylor Swift's first Billboard #1 hit? | We Are Never Ever Getting Back Together | 65%
|
| In what major 2012 dubstep-infused hit did Swift lament a recently ended toxic relationship? | I Knew You Were Trouble | 57%
|