| No. | Term | Definition |
|---|---|---|
| 1. | Adventurous | Eager to explore risks. |
| 2. | Against the grain | Boldly nonconforming. |
| 3. | All-in | Fully committed despite risk. |
| 4. | Audacious | Boldly unconventional or fearless. |
| 5. | Ballsy | Bluntly brave; unafraid. |
| 6. | Bite-the-bullet | Face hardship with courage. |
| 7. | Bold | Confidently brave; willing to risk. |
| 8. | Brash | Bold in a rude way. |
| 9. | Brave | Ready to face danger. |
| 10. | Brazen | Shamelessly bold. |
| 11. | Break the mold | Defy expectations boldly. |
| 12. | Burn your bridges | Commit decisively; no retreat. |
| 13. | By hook or by crook | Boldly determined, any means. |
| 14. | Call your bluff | Challenge bold claims. |
| 15. | Cavalier | Carefree about serious risks. |
| 16. | Chancy | Involving uncertain risk. |
| 17. | Come hell or high water | Persist despite any danger. |
| 18. | Courageous | Showing courage under threat. |
| 19. | Cross the line | Go beyond accepted limits. |
| 20. | Cut and thrust | Bold, vigorous contest. |
| 21. | Damn the torpedoes | Charge ahead despite danger. |
| 22. | Daredevil | One who seeks risky thrills. |
| 23. | Dauntless | Not easily intimidated. |
| 24. | Defiant | Openly resisting authority or danger. |
| 25. | Devil-may-care | Recklessly unconcerned about consequences. |
| 26. | Doughty | Brave and persistent. |
| 27. | Enterprising | Ready to initiate ventures. |
| 28. | Fearless | Without fear. |
| 29. | Feisty | Spiritedly aggressive or bold. |
| 30. | Foolhardy | Recklessly bold; lacking caution. |
| 31. | Fortune favors the bold | Risk can bring reward. |
| 32. | Freewheeling | Unrestrained; taking chances. |
| 33. | Gallant | Brave, noble, and courteous. |
| 34. | Game | Willing to try despite risk. |
| 35. | Go for broke | Risk everything for success. |
| 36. | Go out on a limb | Take a risky position. |
| 37. | Gritty | Tough and resolute. |
| 38. | Gutsy | Showing nerve and courage. |
| 39. | Hardy | Robust; able to endure danger. |
| 40. | Have the nerve | Be bold enough to act. |
| 41. | Heroic | Remarkably brave; noble. |
| 42. | High-spirited | Lively; boldly energetic. |
| 43. | Hotheaded | Impulsively bold; quick to act. |
| 44. | Impetuous | Acting quickly without thought. |
| 45. | In the teeth of danger | Facing danger directly. |
| 46. | In-your-face | Aggressively bold and direct. |
| 47. | Intrepid | Fearless in face of danger. |
| 48. | Jaw-dropping | Astonishingly bold or extreme. |
| 49. | Keep a stiff upper lip | Endure hardship without complaint. |
| 50. | Leap before you look | Act without considering risks. |
| 51. | Lionhearted | Brave and strong-willed. |
| 52. | Macho | Aggressively masculine; bold. |
| 53. | Make waves | Cause bold disruption. |
| 54. | Maverick | Independent-minded risk taker. |
| 55. | Nerve-racking | Tense; involving great risk. |
| 56. | Nervy | Boldly cheeky or brave. |
| 57. | No guts, no glory | Reward requires risk. |
| 58. | No-holds-barred | Without restraint; very bold. |
| 59. | On the edge | In a risky situation. |
| 60. | Outspoken | Boldly frank in speech. |
| 61. | Play with fire | Take dangerous risks. |
| 62. | Plucky | Bravely determined. |
| 63. | Pugnacious | Eager to fight; combative. |
| 64. | Punchy | Forcefully energetic; bold. |
| 65. | Push the envelope | Extend limits boldly. |
| 66. | Raise eyebrows | Shock with boldness. |
| 67. | Rash | Hastily risking consequences. |
| 68. | Rebellious | Resisting control; boldly disobedient. |
| 69. | Reckless | Careless of danger. |
| 70. | Resolute | Firmly determined despite risk. |
| 71. | Risk-taking | Willing to accept danger. |
| 72. | Rowdy | Noisy, unruly, and bold. |
| 73. | Sassy | Boldly cheeky; impertinent. |
| 74. | Savage | Fiercely bold; ruthless. |
| 75. | Scrappy | Determined and ready to fight. |
| 76. | Shameless | Unembarrassed; boldly improper. |
| 77. | Shoot from the hip | Act or speak impulsively. |
| 78. | Spirited | Full of bold energy. |
| 79. | Spunky | Lively, brave, and determined. |
| 80. | Stick your neck out | Take a personal risk. |
| 81. | Stouthearted | Brave and determined. |
| 82. | Strident | Forcefully assertive; boldly loud. |
| 83. | Take the bull by horns | Confront danger directly. |
| 84. | Temerarious | Recklessly bold; rash. |
| 85. | Tenacious | Stubbornly persistent under pressure. |
| 86. | Thick-skinned | Unafraid of criticism. |
| 87. | Throw caution to the wind | Act without restraint. |
| 88. | To hell with it | Recklessly dismiss consequences. |
| 89. | Trailblazing | Innovatively bold; setting new paths. |
| 90. | Unabashed | Not ashamed; openly bold. |
| 91. | Unbowed | Not defeated or humbled. |
| 92. | Undaunted | Not discouraged by danger. |
| 93. | Unflinching | Not shrinking from pain or fear. |
| 94. | Uninhibited | Free from restraint; boldly expressive. |
| 95. | Unorthodox | Boldly unconventional. |
| 96. | Unruly | Hard to control; boldly disorderly. |
| 97. | Unshakable | Firm; not easily frightened. |
| 98. | Valiant | Bravely determined. |
| 99. | Venturesome | Ready to take risks. |
| 100. | Visionary | Boldly imaginative and forward-looking. |