50 Best Country Songs About Taking a Chance on Love

Best Country Songs for Risking Love

There’s a certain edge to taking a leap with someone new. It’s not pure thrill, not quite panic, but a messy blend that feels sharp in the chest. The moment hangs in that strange space where you’re unsure if you’re walking into heartbreak or stumbling into the thing you’ll tell stories about years later. Country music thrives here. The guitars lean into it, the vocals stretch it out, and the lyrics sit in the awkward middle ground between brave and reckless. Some tracks spell it out clearly while others only brush past the theme, but they all capture that jittery pull of rolling the dice.

Love never lands clean. It can start in a smoky bar where you talk louder than you should, or in the quiet stretch of a car ride when the words tumble out before you’ve thought them through. It might show up in ways that sound closer to pop, rock, country, and R&B songs, but the thread tying them together is the gamble. These tracks don’t pretend the risk is neat or polished. They don’t smooth the edges to make things comfortable. Instead, they sit in the uncertainty, letting it ache a little, letting it buzz with the kind of electricity you can’t fake.

It’s not always fresh or bright. Sometimes it feels like running into something you know could wreck you, and that’s exactly why it pulls so hard. The best songs that lean into this theme understand the mess, the thrill, the strange kind of courage that comes with stepping forward anyway. Some may not be literally tied to the idea, but they fit the mood all the same. Here are the best country songs for risking love.

1. 'Love Story' by Taylor Swift

2. 'Yours' by Russell Dickerson

3. 'The Bones' by Maren Morris

4. 'Forever After All' by Luke Combs

5. 'It Won't Be Long' by George Birge

6. 'The Good Ones' by Gabby Barrett

7. 'Love You Anyway' by Luke Combs

8. 'Leap of Faith' by Lionel Cartwright

9. 'How Do I Live' by LeAnn Rimes

10. 'I Hope You Dance' by Lee Ann Womack

11. 'You're Still the One' by Shania Twain

12. 'Beautiful Crazy' by Luke Combs

13. 'Die a Happy Man' by Thomas Rhett

14. 'In Case You Didn't Know' by Brett Young

15. 'Bless the Broken Road' by Rascal Flatts

16. 'Crazy Girl' by Eli Young Band

17. 'Amazed' by Lonestar

18. 'My Best Friend' by Tim McGraw

19. 'I Cross My Heart' by George Strait

20. 'I Can Love You Like That' by John Michael Montgomery

21. 'A Little Bit Stronger' by Sara Evans

22. 'You'll Think of Me' by Keith Urban

23. 'Check Yes Juliet' by We the Kings

24. 'Kiss Me' by Sixpence None the Richer

25. 'Just a Kiss' by Lady A

26. 'I Do' by Colbie Caillat

27. 'Wanted' by Hunter Hayes

28. 'From the Ground Up' by Dan + Shay

29. 'I Can't Make You Love Me' by Bonnie Raitt

30. 'More Than a Memory' by Garth Brooks

31. 'I Swear' by John Michael Montgomery

32. 'When I Said I Do' by Clint Black with Lisa Hartman Black

33. 'I Can't Stop Loving You' by Ray Charles

34. 'I Don't Dance' by Lee Brice

35. 'God Gave Me You' by Blake Shelton

36. 'Then' by Brad Paisley

37. 'Making Memories of Us' by Keith Urban

38. 'Something Like That' by Tim McGraw

39. 'Hey Pretty Girl' by Kip Moore

40. 'I Saw the Light' by Hank Williams

41. 'You Look Like You Love Me' by Ella Langley featuring Riley Green

42. 'Something 'Bout a Sunday' by Ira Dean

43. 'No Place That Far' by Sara Evans

44. 'I Got a Boy' by Ella Langley

45. 'I Don't Know What I'm Doing' by Cody Johnson

46. 'You Look Good in My Shirt' by Keith Urban

47. 'A Thousand Years' by Christina Perri

48. 'I Would've Loved You Anyway' by Trisha Yearwood

49. 'She's Everything' by Brad Paisley

50. 'You'll Accomp'ny Me' by Bob Seger