Sometimes you need a quick win. A 5-minute icebreaker. A way to wake up a sleepy Monday meeting. A low-pressure activity that gets people talking without asking them to “share a fun fact” (please, no more fun facts).

Enter: Would You Rather.

It’s simple. It’s nostalgic. And when done right, it sparks connection without putting anyone on the spot.

Let’s get into it!

⭐ Everyday Life: Non-Work Edition

1. Would you rather always have the perfect playlist for every moment or always have the perfect outfit?
2. Would you rather live somewhere it’s always fall or always spring?
3. Would you rather have unlimited time or unlimited energy?
4. Would you rather be the funniest person in the room or the smartest?
5. Would you rather always get the window seat or never sit in traffic again?
6. Would you rather have a rewind button or a fast-forward button for life?
7. Would you rather be an early bird naturally or a night owl naturally?
8. Would you rather always remember names or never forget where you parked?
9. Would you rather have a personal chef or a personal driver?
10. Would you rather be great at small talk or great at deep conversations?

🏆 Work Style & Team Dynamics

11. Would you rather start work at 7am and leave early or start at 10am and work late?
12. Would you rather work four 10-hour days or five 8-hour days?
13. Would you rather always be slightly early or slightly late?
14. Would you rather have walking meetings or camera-off meetings?
15. Would you rather have your team surprise you with a celebration or get to plan your own perfect celebration?
16. Would you rather have a “no meetings” day every week or a “no email” day every week?
17. Would you rather communicate only via Slack or only via email?
18. Would you rather have your own office playlist on speakers or complete silence?
19. Would you rather present to executives or facilitate a team workshop?
20. Would you rather earn a surprise bonus or get an extra paid week off?
21. Would you rather be the idea person or the execution person?
22. Would you rather brainstorm in a group or think independently?
23. Would you rather have back-to-back meetings one day or spread throughout the week?
24. Would you rather receive public recognition or private praise?
25. Would you rather work on one big project or many small ones?
26. Would you rather try something new or optimize something existing?
27. Would you rather shadow another department for a week or teach your role to someone else for a week?
28. Would you rather have a super fast-paced environment or a steady one?
29. Would you rather work from anywhere in the world for a year or take one month completely unplugged?
30. Would you rather celebrate small wins or big milestones?

🍕 Food & Drink Favorites

31. Would you rather host a team bake-off or a mystery ingredient cooking challenge?
32. Would you rather invent a new ice cream flavor or a new holiday dessert?
33. Would you rather eat breakfast for every meal or dinner for every meal?
34. Would you rather try a new cuisine every week or stick to your favorites forever?
35. Would you rather have a personal food critic narrate every meal you eat or have to rate every meal publicly?
36. Would you rather eat only crunchy foods or only soft foods?
37. Would you rather give up coffee or give up dessert?
38. Would you rather have to dip everything in sauce or never use sauce again?
39. Would you rather do a team cooking class or a team mixology class?
40. Would you rather have your favorite meal once a week or try something brand new every week?

🌎 Travel & Adventure

41. Would you rather take a beach vacation or a mountain getaway?
42. Would you rather explore a new country or revisit your favorite place?
43. Would you rather go on a road trip or take a flight?
44. Would you rather be the planner or just show up for the trip?
45. Would you rather camp outdoors or stay in a luxury hotel?
46. Would you rather try skydiving or scuba diving?
47. Would you rather take a group tour with strangers or design a totally custom trip?
48. Would you rather take one long vacation or multiple mini getaways?
49. Would you rather live abroad for a year or travel somewhere new every month for a year?
50. Would you rather have a team retreat in the city or in nature?

🎨 Creativity & Hobbies

51. Would you rather take a painting class or a dance class?
52. Would you rather learn a new language or learn a new instrument?
53. Would you rather read the book or watch the movie?
54. Would you rather do a DIY craft night or a trivia night?
55. Would you rather have unlimited books or unlimited podcasts?
56. Would you rather try pottery or photography?
57. Would you rather join a sports league or a book club?
58. Would you rather write a short story or create a short film?
59. Would you rather learn baking or bartending?
60. Would you rather be amazing at public speaking or amazing at writing?

🤪 Off the Wall (But Still HR-Safe)

61. Would you rather have to sing your presentations or dance your presentations?
62. Would you rather only use emojis in Slack or only use GIFs?
63. Would you rather have a theme song play every time you join a meeting or a spotlight shine on you?
64. Would you rather swap jobs with a teammate for a day or with your CEO for a day?
65. Would you rather have a meeting with no agenda or an agenda that’s 3 pages long?
66. Would you rather work in pajamas forever or in business formal forever?
67. Would you rather have a pet in every meeting or a plant you must care for during meetings?
68. Would you rather only type in all caps or never use punctuation?
69. Would you rather time-travel to the past or to the future for one workday?
70. Would you rather narrate your workday or have it narrated by someone else?

🧠 Thoughtful & Surprisingly Deep

71. Would you rather be known for your kindness or your expertise?
72. Would you rather make a big impact on a small team or a small impact on a huge organization?
73. Would you rather take a big risk or play it safe?
74. Would you rather master one skill or be good at many?
75. Would you rather be constantly learning something new or constantly improving what you already know?
    

How to Use These Questions at Work

A few easy ways to make the most of them:

• Use 1–2 as a meeting opener.
• Post one weekly in Slack.
• Turn them into breakout room prompts.
• Have team members submit their own.
• Use them as part of onboarding to help new hires connect.

The magic isn’t in the question itself — it’s in the conversation that follows.

Ready to Turn Icebreakers Into Real Connection?

Fun questions are a great start. But the real culture-building happens when connection becomes a habit, not just a once-in-a-while activity.

If you want plug-and-play experiences that spark conversation, build trust, and make meetings something people actually look forward to, that’s exactly what we do at Confetti.

From team-building events to ready-to-run meeting kits, we help you create moments that matter (without adding more to your plate).

👉 Explore experiences that bring your team together at withconfetti.com.

Because “How was everyone’s weekend?” can only take you so far 💛