50 Best Country Songs About Fumbling a Girl
Country breakup songs where the guy blew it
There’s a strange punch in the gut when you realize you had it and let it slip. Not in a sweeping, tragic movie scene kind of way, but in the quiet moments after she’s already gone. You’re sitting in the truck, replaying a conversation you thought you won, only to hear how dumb it sounded the second time around. Some of these songs catch that blur between regret and disbelief, the kind that makes you check your phone even though you know she’s not calling. The lines hit harder because you know the screw-up came from your own side.
Nobody’s swaggering through these tracks like the hero of a honky-tonk night. It’s the late drives with the radio low, the shuffle through bars where every neon sign feels like it’s pointing at you. The voices crack in places you notice, because the singers aren’t smoothing over their mistakes. There’s a rawness in the way they tell it that runs close to certain pop, rock, country, and R&B songs built on the same kind of self-inflicted loss. It’s not about winning her back with some big gesture, more the slow crawl toward admitting you blew your best shot.
Some of these tracks ache. Others sting quick and get out. A few lean into humor because that’s all you’ve got left when the door’s closed and you’re still talking to yourself. They all carry a piece of that awkward, familiar sting you can’t quite shake no matter how many spins you give them. Here are the best country songs for when you fumble the girl.
Top 10 Country Regret Songs
1. 'Whiskey and You'—Chris Stapleton
2. 'I'm Sorry'—Blake Shelton
3. 'Why'—Jason Aldean
4. 'Here Comes Goodbye'—Rascal Flatts
5. 'You Didn't'—Brett Young
6. 'Die From a Broken Heart'—Maddie and Tae
7. 'Don't Think I Don't Think About It'—Darius Rucker
8. 'I'd Be Better Off In a Pine Box'—Doug Stone
9. 'What If I Never Get Over You'—Lady A
10. 'The Dance'—Garth Brooks
Country Songs About Wasted Words #11—20
11. 'I Drive Your Truck'—Lee Brice
12. 'Always on My Mind'—Willie Nelson
13. 'I Remember Everything'—Zach Bryan featuring Kacey Musgraves
14. 'He Stopped Loving Her Today'—George Jones
15. 'One More Last Chance'—Vince Gill
16. 'What Hurts the Most'—Rascal Flatts
17. 'You'll Think of Me'—Keith Urban
18. 'Colder Weather'—Zac Brown Band
19. 'Need You Now'—Lady A
20. 'Break Up in a Small Town'—Sam Hunt
Country Songs About Second Chances #21—30
21. 'You Should Be Here'—Cole Swindell
22. 'Second Chances'—Kelsey Lamb
23. 'One Second Chance'—Jeff Bates
24. 'What If'—Kane Brown
25. 'Like We Never Loved at All'—Tim McGraw and Faith Hill
26. 'I Wouldn't Be a Man'—Josh Turner
27. 'Wish I Didn't Know Now'—Toby Keith
28. 'That's a Mistake'—Riley Green
29. 'For Her'—Chris Lane
30. 'Another Try'—Josh Turner
Country Songs About Missing an Ex #31—40
31. 'I Fall to Pieces'—Patsy Cline
32. 'Neon Moon'—Brooks & Dunn
33. 'Someone Else Calling You Baby'—Luke Bryan
34. 'I'm So Lonesome I Could Cry'—Hank Williams
35. 'Give It Away'—George Strait
36. 'Always on My Mind'—Dolly Parton
37. 'Fire Away'—Chris Stapleton
38. 'Don't Close Your Eyes'—Keith Whitley
39. 'Brokenheartsville'—Joe Nichols
40. 'Goodbye Time'—Blake Shelton
Country Songs About Lost Love #41—50
41. 'Whiskey Lullaby'—Brad Paisley featuring Alison Krauss
42. 'The Long Black Veil'—Johnny Cash
43. 'For My Broken Heart'—Reba McEntire
44. 'If I Didn't Love You'—Jason Aldean and Carrie Underwood
45. 'Caroline'—Colter Wall
46. 'I Will Always Love You'—Dolly Parton
47. 'Concrete Angel'—Martina McBride
48. 'If Tomorrow Never Comes'—Garth Brooks
49. 'She's Gone, Gone, Gone'—Lee Ann Womack
50. 'Go Rest High on That Mountain'—Vince Gill
© 2025 Carson McQueen
