50 Best Country Songs About High School Sweethearts
High School Love Stories in Country Music
There’s a certain kind of nostalgia that clings to songs tied to high school sweethearts. Not the polished, scrapbook kind but the raw mix of inside jokes, long drives, and arguments in parking lots. Those memories hit different when set to a steel guitar or a slow fiddle line. You can almost see the letterman jacket tossed over a chair, the late-night phone calls when curfews were being ignored, and the steady hum of a future nobody could picture yet. These tracks tap into that haze where every moment felt huge and small at the same time.
It’s not all golden-hour perfection. Some stories fade out under the glow of stadium lights. Others get tangled in jealousy or the quiet drift that comes when graduation creeps closer. The charm is in the details the worn-out boots on a Friday night date, the playlists mixing pop, rock, country, and R&B songs for the ride home, the hopeful promises scribbled into yearbooks. Country artists tend to linger there a little longer than most, stretching out those moments until you can smell the grass from the football field again.
And then there are the tracks that pull no punches on the heartbreak. The ones that keep the same slow sway but let the cracks show in the harmonies. They don’t smooth over the endings or pretend everyone stayed in touch. They let the listener sit in the ache for a bit, which might be why they stick around in your head. Here’s a rundown of the best Country Songs About High School Sweethearts.
Top 10 High School Romance Country Songs
1. 'She's in Love with the Boy'—Trisha Yearwood
2. 'Check Yes or No'—George Strait
3. 'Strawberry Wine'—Deana Carter
4. 'Forever and Ever, Amen'—Randy Travis
5. 'Then'—Brad Paisley
6. 'The Rest of Our Life'—Tim McGraw & Faith Hill
7. 'In Case You Didn't Know'—Brett Young
8. 'I Cross My Heart'—George Strait
9. 'Speechless'—Dan + Shay
10. 'Die a Happy Man'—Thomas Rhett
Country Music Hits From #11—20
11. 'You're Still the One'—Shania Twain
12. 'Bless the Broken Road'—Rascal Flatts
13. 'Amazed'—Lonestar
14. 'Love Story'—Taylor Swift
15. 'From the Ground Up'—Dan + Shay
16. 'The Dance'—Garth Brooks
17. 'Remember When'—Alan Jackson
18. 'I Swear'—John Michael Montgomery
19. 'Me and You'—Kenny Chesney
20. 'I Love You'—Martina McBride
Country Songs About Enduring Love #21—30
21. 'Little Moments'—Brad Paisley
22. 'Better Together'—Luke Combs
23. 'I Run to You'—Lady A
24. 'It's Your Love'—Tim McGraw & Faith Hill
25. 'Through the Years'—Kenny Rogers
26. 'When I Said I Do'—Clint Black
27. 'You Decorated My Life'—Kenny Rogers
28. 'Lost in This Moment'—Big & Rich
29. 'Nobody But You'—Blake Shelton and Gwen Stefani
30. 'When You Say Nothing at All'—Alison Krauss
Country Songs on Relationships and Romance #31—40
31. 'Forever and For Always'—Shania Twain
32. 'The Kind of Love We Make'—Luke Combs
33. 'I Just Can't Let Go'—John Conlee
34. 'I Need You'—Tim McGraw & Faith Hill
35. 'Young Love'—Kip Moore
36. 'Love Like Crazy'—Lee Brice
37. 'It Must Be Love'—Alan Jackson
38. 'Love Without End, Amen'—George Strait
39. 'Hey Pretty Girl'—Kip Moore
40. 'Half of My Hometown'—Kelsea Ballerini ft. Kenny Chesney
Country Songs About First Love #41—50
41. 'Whiskey Lullaby'—Brad Paisley ft. Alison Krauss
42. 'The Boys of Fall'—Kenny Chesney
43. 'American Country Love Song'—Jake Owen
44. 'Old School'—John Conlee
45. 'Simple'—Florida Georgia Line
46. 'Story of You and Me'—Sam Riggs
47. 'Our Song'—Taylor Swift
48. 'The House That Built Me'—Miranda Lambert
49. 'Young'—Kenny Chesney
50. 'Could I Have This Dance'—Anne Murray
© 2025 Carson McQueen
