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That sounds like a fun game! Here's a pick from each Taylor Swift album:

1. Taylor Swift (2006) - "Tim McGraw"
2. Fearless (2008) - "Fifteen"
3. Speak Now (2010) - "Enchanted"
4. Red (2012) - "All Too Well" (10-Minute Version)
5. 1989 (2014) - "Blank Space"
6. Reputation (2017) - "Delicate"
7. Lover (2019) - "Lover"
8. Folklore (2020) - "Exile" (feat. Bon Iver)
9. Evermore (2020) - "Champagne Problems"
10. Fearless (Taylor's Version) (2021) - "Fearless"
11. Midnights (2022) - "Karma"

Let me know which song(s) resonates with you or your favorite among these!