The Ultimate Guide to “This or That”: 100 Provocative Questions to Spark Real Conversations

If you’ve ever watched Family Guy, you’ve seen how the show takes simple scenarios and turns them into laugh-out-loud, over-the-top moments. “This or That” questions work in a similar way, where seemingly straightforward choices spark hilarious or insightful conversations. This game is perfect for bringing people closer and getting to know one another, whether it’s at a social gathering or in a professional setting. Plus, for those planning team events, this simple game is a fantastic icebreaker; teambuildingawards.com offers awards for the best team-building moments, and “This or That” is a perfect nominee!

Why “This or That” Questions Work

The genius of “This or That” lies in its simplicity: present two contrasting choices and ask participants to pick one. The format is versatile, appealing to all ages and adaptable for any occasion. It’s a surefire way to ease social tensions, create memorable conversations, and help people bond over shared beliefs or debates over opposing views. These questions can be lighthearted or profound, playful or intense. Best of all, they work equally well in person and virtually.

The Many Benefits of “This or That”

• Break the Ice: Quickly get past small talk and dive into questions that reveal more about who we are.
• Strengthen Connections: Discover new things about friends, family, and colleagues, building rapport in the process.
• Encourage Reflection: Force yourself and others to ponder preferences and values that might not come up otherwise.
• Create Fun and Laughter: Not every question has to be serious; some are just plain fun!

100 Provocative “This or That” Questions for Memorable Conversations

Love, Life, and Relationships

1. Love or money?
2. Passion or stability?
3. Romantic partner or best friend?
4. Change the past or see the future?
5. Alone forever or surrounded by people you don’t like?
6. Forgive and forget or remember and learn?
7. Loyalty or honesty?
8. Love deeply and lose or never love at all?
9. One true love or several great loves?
10. Fall in love fast or let love grow slowly?

Deep Philosophical Choices

11. Free will or destiny?
12. Logic or emotion?
13. Revenge or forgiveness?
14. Always know the truth or always live in blissful ignorance?
15. Fame for something you regret or no fame at all?
16. Success or happiness?
17. Wealth or wisdom?
18. All-knowing or all-powerful?
19. To be feared or to be loved?
20. Freedom or security?

Self and Personal Growth

21. Be popular or be authentic?
22. Adventure or safety?
23. Be the first to apologize or wait for the apology?
24. Change the world or change yourself?
25. Stand out or fit in?
26. Make a big mistake or never take any risks?
27. Be mysterious or be an open book?
28. Always speak your mind or never speak again?
29. Selfless or selfish?
30. Intense, short-lived romance or steady, lasting relationship?

Dreams, Goals, and Desires

31. Rich but miserable or poor but happy?
32. Pursue your dream or settle for stability?
33. Be adored or be respected?
34. Give or receive?
35. Make an impact or live at peace?
36. Look into the past or into the future?
37. Time travel or teleportation?
38. Control your dreams or control your thoughts?
39. Live an extraordinary life that’s short or a normal life that’s long?
40. Fame or freedom?

Hypothetical Scenarios

41. Be famous in life or remembered after death?
42. Travel the world with no money or stay in one place with unlimited wealth?
43. Intelligent and lonely or happy but ignorant?
44. Strong physical attraction or strong emotional connection?
45. Forbidden love or arranged marriage?
46. Live in luxury or live with love?
47. Face your fears or avoid them forever?
48. Be the hero or the villain?
49. Dark humor or light-hearted humor?
50. Peace or passion?

Social Choices and Beliefs

51. Trust everyone or trust no one?
52. Private life or public life?
53. Truth or dare?
54. Be envied or be admired?
55. Be feared for your power or loved for your kindness?
56. Introvert or extrovert?
57. Break someone’s heart or get your heart broken?
58. Fame and fortune or quiet, peaceful life?
59. Quit or keep trying?
60. Speak your truth or protect someone’s feelings?

Everyday Life and Lifestyle

61. Early bird or night owl?
62. Work from home or office?
63. City or countryside?
64. Public speaking or death?
65. Burn bridges or keep toxic ties?
66. Be a realist or be a dreamer?
67. Coffee or tea?
68. Pizza or pasta?
69. Summer or winter?
70. Cats or dogs?

Fun and Lighthearted

71. Comedy or drama?
72. Movies or books?
73. Road trip or flight?
74. Sweet or savory?
75. Wine or beer?
76. Adventure or relaxation?
77. Reading or writing?
78. Dark chocolate or milk chocolate?
79. Sushi or tacos?
80. Stay in or go out?

Unique and Challenging

81. Physical attraction or emotional connection?
82. Date someone with a good heart or a great mind?
83. Find your calling or find your soulmate?
84. Best night of your life once or a good life every day?
85. Be extremely talented or extremely intelligent?
86. Lose all memories or lose your ability to make new ones?
87. Trust everyone or trust no one?
88. Always win or always learn?
89. Be in a movie or write the movie?
90. Live in a world without hate or without love?

Hypotheticals and Dilemmas

91. Have no regrets or no mistakes?
92. Have no social media or be unable to go offline?
93. Adventure or safety?
94. Give up all your possessions for a year or never travel again?
95. Always be right or always be kind?
96. Be stuck in a small town or lost in a big city?
97. Find true love but lose a friend or keep all friends but never find love?
98. Physical beauty or inner beauty?
99. Forgive your greatest enemy or hold a grudge forever?
100. Dark humor or light-hearted humor?

Making “This or That” Work for You

Whether you’re using these questions to break the ice or spark some serious conversation, they’re adaptable to nearly any setting. Here’s how to maximize their impact:

• Set the Right Tone: Some questions can be intense, so gauge your group’s vibe before diving into the deeper ones.
• Encourage Openness: People are more likely to share if they feel safe. Be respectful of all responses.
• Mix Lighthearted and Deep Questions: Keep it fun, but don’t shy away from those meaningful questions that could reveal a lot about each person.
• Make It Personal: Add your twist to any question, making it relevant to your audience.

Final Thoughts

“Provocative This or That” questions have the power to uncover sides of ourselves and others that might otherwise stay hidden. They’re not only fun and insightful, but they’re also a reminder of the complex, multifaceted nature of human relationships. Whether you’re aiming for a good laugh or a deep discussion, these questions will ensure your next gathering, meeting, or virtual hangout is anything but dull.