| Hint | Song Title | Album |
| A First Scar Break-Up Song | |
| A Song Remembering a Relationship | |
| Apology Song For a Certain Name-Sharing Ex-Boyfriend | |
| A Song About Body Parts Found Above Your Nose | |
| Written About a First Date | |
| 'Nothing's Quite Like _____ ______ _____ _____' | |
| Featuring Colbie Callet | |
| Break-Up Song | |
| He Left on a Plane | |
| 'Just Know I'm Right Here Hoping...' | |
| Written for the Hannah Montana Movie | |
| Also the Title of Nicholas Sparks' Famous Book | |
| The Inspiration for Her Two Fragrances | |
| With Ed Sheeran | |
| Named an Album | |
| First Day of School, Making Friends, First Boyfriend, First Kiss... | |
| Supposedly Written About Joe Jonas | |
| He Wants to Cheat on His Girl with Taylor | |
| During Concert, Taylor Rings a Bell with 'XIII' On It | |
| About a Boy Named Stephen | |
| Reminiscing About a Relationship | |
| 'Every Time I Don't...' | |
| Second Song on Taylor's 2-Song Album | |
| A 'Looking Back, I Knew This Would Happen' Kind of Song | |
| She Knows Everything About Him, But if Asked if She Loved Him, She Wouldn't Tell the Truth | |
| 'Friday Night Beneath the Stars' | |
| A Bonus Track | |
| I Like Him, He Likes Her | |
| Scared to Fall In Love? Don't Worry, I'll Catch You | |
| Break-Up | |