The Ultimate List of "Would You Rather" Questions for Families

Nothing sparks laughter faster than a great Would You Rather showdown. Whether you are cruising down the interstate or gathered for a cozy game night, these prompts help everyone share preferences, values, and silly imagination. Load them into MileSmile, switch on hands-free Car Mode, and let the steering wheel buttons keep the game rolling while the driver stays focused.

How to Play on the Go

• Stay hands-free: Turn on Car Mode so MileSmile reads each question aloud and you control everything from the wheel.
• Pick a vibe: Choose the category that matches your energy—silly, thoughtful, or travel-inspired.
• Rotate storytellers: After each vote, ask one person to explain their choice for deeper conversation.
• Keep score (or not): Use in-app polls for quick votes or simply enjoy the dialogue.

Quick-Choose Categories

Category	Best For	MileSmile Tip
Road Trip Classics	First hour of a drive	Enable narration so everyone hears the prompt at the same time.
Food Fights (the fun kind)	Snack breaks	Use Quick Play for fast votes before the next exit.
Travel & Adventure	Mapping stops	Bookmark answers to inspire detours and future trips.
Home & Heart	Evening wind-down	Try the Calm voice pack for a softer tone.
Laugh-Out-Loud	Energy slumps	Add sound effects to celebrate the most creative answers.

Each category continues the numbering so you can track progress. Mix and match to keep energy fresh on every mile.

Road Trip Classics (1-20)

1. Would you rather listen to one perfect playlist all trip or let each passenger DJ for 15 minutes?
2. Would you rather stop at quirky roadside attractions or power through to arrive early?
3. Would you rather pack all snacks from home or try something new at every gas station?
4. Would you rather take the scenic route with views or the fastest route with no stops?
5. Would you rather sit by the window on every drive or always claim the co-pilot seat?
6. Would you rather have every rest stop include a picnic or a quick stretching game?
7. Would you rather have the car read questions aloud or see them as cards on the dash?
8. Would you rather sing along to classics or try karaoke challenges from MileSmile?
9. Would you rather drive at sunrise or at dusk for golden-hour views?
10. Would you rather play trivia every 20 miles or Would You Rather every 10?
11. Would you rather choose the music for the entire day or choose all the snack stops?
12. Would you rather travel with a surprise itinerary or plan every landmark together?
13. Would you rather have the best roadside diner breakfast or the perfect campfire dinner?
14. Would you rather stop for a scenic photo every hour or save all photos for one epic location?
15. Would you rather drive through mountains or along the coast?
16. Would you rather let the youngest passenger pick the next game or the oldest?
17. Would you rather have unlimited audiobooks or unlimited podcast episodes?
18. Would you rather pack super light or bring every comfort item you love?
19. Would you rather have clear starry skies every night or perfect sunshine every day?
20. Would you rather have a spontaneous detour to a small town or a planned stop at a famous landmark?

Food Fights (21-40)

21. Would you rather eat breakfast for dinner or dinner for breakfast on a road trip?
22. Would you rather try every regional dessert or every regional savory dish?
23. Would you rather never eat fries again or never eat pizza again?
24. Would you rather have unlimited trail mix or unlimited fruit snacks for the car?
25. Would you rather cook together at a campsite or find the best local food truck?
26. Would you rather only drink sparkling water or only still water for the whole drive?
27. Would you rather share one giant snack box or let everyone keep their own stash?
28. Would you rather try a mystery milkshake flavor or a mystery sandwich?
29. Would you rather choose the restaurant for every stop or choose the dessert every time?
30. Would you rather never eat chocolate again or never eat cheese again?
31. Would you rather have a picnic at every overlook or eat at every quirky diner?
32. Would you rather have the perfect cup of coffee or the perfect smoothie every morning?
33. Would you rather have bottomless popcorn or bottomless nachos for movie nights on the road?
34. Would you rather invent a new family sandwich or a new family ice cream flavor?
35. Would you rather grow your own herbs for cooking or bake fresh bread every weekend?
36. Would you rather choose the snacks for today or the meals for the entire vacation?
37. Would you rather taste-test hot sauces or sample every type of jam?
38. Would you rather give up candy until the next rest stop or give up soda until the destination?
39. Would you rather organize a family cook-off or host a neighborhood potluck?
40. Would you rather never eat out again or never cook at home again?

Travel & Adventure (41-70)

41. Would you rather explore a national park or a bustling city?
42. Would you rather camp under the stars or stay in a funky boutique hotel?
43. Would you rather learn a local dance or a local recipe on every trip?
44. Would you rather take a road trip across one state slowly or dash across three states in a week?
45. Would you rather see a famous landmark at sunrise or sunset?
46. Would you rather swim in a lake or hike to a waterfall?
47. Would you rather spot wildlife on a safari drive or go whale watching from a boat?
48. Would you rather travel by train for a year or by RV for a year?
49. Would you rather have perfect weather every trip or free upgrades on every stay?
50. Would you rather take a surprise detour recommended by a local or stick to the plan?
51. Would you rather learn a new language together or master a new instrument together?
52. Would you rather visit every national park or every major museum?
53. Would you rather take photos on film or only on a vintage camcorder?
54. Would you rather try rock climbing or paddleboarding as a family?
55. Would you rather explore underground caves or climb a lighthouse?
56. Would you rather travel only in winter or only in summer?
57. Would you rather keep a travel journal or make a travel podcast?
58. Would you rather explore one country in depth or visit ten countries briefly?
59. Would you rather take a cooking class in every city or a street art tour in every city?
60. Would you rather bike through vineyards or kayak through marshlands?
61. Would you rather return to your favorite destination yearly or always try somewhere new?
62. Would you rather have a weekend of theme parks or a weekend of nature hikes?
63. Would you rather travel with only a backpack or with one shared suitcase?
64. Would you rather map the route yourself or let MileSmile randomize the next stop?
65. Would you rather volunteer on vacation or focus entirely on relaxation?
66. Would you rather have unlimited roadside photo ops or unlimited roadside coffee?
67. Would you rather meet new friends on every trip or stick with just the family crew?
68. Would you rather see a concert in every city or a sports game in every city?
69. Would you rather build a sandcastle contest or a snow sculpture contest?
70. Would you rather wake up for sunrise hikes or stay up late for stargazing?

Home, Heart, and Traditions (71-95)

71. Would you rather host every holiday or travel for every holiday?
72. Would you rather keep one cherished family tradition or start a new one each year?
73. Would you rather have a weekly family walk or a weekly family board game night?
74. Would you rather decorate the house for every season or only for big holidays?
75. Would you rather cook a giant meal together or do a giant clean-up together?
76. Would you rather share a gratitude practice or a storytelling practice before bed?
77. Would you rather record family interviews every year or make a highlight reel of videos?
78. Would you rather keep handwritten letters or digital photo books?
79. Would you rather spend Saturdays volunteering together or taking a class together?
80. Would you rather plan a monthly family outing or a big yearly adventure?
81. Would you rather swap chores for a week or swap favorite hobbies for a day?
82. Would you rather redesign the living room together or plant a garden together?
83. Would you rather adopt a pet now or foster pets throughout the year?
84. Would you rather keep a memory box or a digital timeline of highlights?
85. Would you rather have a monthly theme night (tacos, trivia, travel) or a surprise challenge night?
86. Would you rather share one goal for the month or each pick your own and check in weekly?
87. Would you rather create a family motto or a family playlist?
88. Would you rather learn a new skill together or teach each other existing skills?
89. Would you rather spend a day offline each week or have one tech-free room in the house?
90. Would you rather make every Sunday brunch special or every Friday movie night epic?
91. Would you rather pass down a recipe book or a playlist of favorite songs?
92. Would you rather plant a tree for every big milestone or take a photo in the same spot every year?
93. Would you rather be known for your hospitality or your sense of adventure?
94. Would you rather have a family book club or a family maker club?
95. Would you rather create a shared wish list for experiences or for gadgets?

Laugh-Out-Loud & Imagination (96-120)

96. Would you rather have to rhyme every sentence or sing every sentence?
97. Would you rather have marshmallow shoes or spaghetti hair?
98. Would you rather ride to school on a dragon or a giant eagle?
99. Would you rather have a pause button or a rewind button for your day?
100. Would you rather talk like a pirate for a week or like a robot for a week?
101. Would you rather only whisper or only shout for one day?
102. Would you rather have a pet dinosaur or a pet robot?
103. Would you rather have to hop everywhere or dance everywhere?
104. Would you rather swap voices with a sibling or swap favorite snacks?
105. Would you rather eat ice cream with chopsticks or cereal with a fork?
106. Would you rather turn invisible for one hour a day or fly for five minutes a day?
107. Would you rather live in a treehouse or a houseboat?
108. Would you rather have a tiny elephant or a giant hamster as a pet?
109. Would you rather be able to speak to animals or speak every language?
110. Would you rather sleep in a room full of glowing stars or glowing jellyfish (friendly ones)?
111. Would you rather have pizza-scented pillows or marshmallow carpets?
112. Would you rather host a costume breakfast or a pajama parade?
113. Would you rather live in a world made of candy or a world made of LEGOs?
114. Would you rather tell a joke every time you meet someone or give a high five every time?
115. Would you rather ride to school on a unicycle or on roller skates?
116. Would you rather have to invent a new handshake with everyone or invent a new nickname for everyone?
117. Would you rather eat dinner for breakfast or breakfast for dinner forever?
118. Would you rather have musical sound effects follow you or a personal narrator?
119. Would you rather build a blanket fort in every hotel or create a scavenger hunt at every park?
120. Would you rather have a magic backpack that produces snacks or one that produces board games?

Make It Hands-Free with MileSmile

Load these prompts into MileSmile and tap Car Mode before you shift into drive. The app will read each question aloud, and you can flip to the next prompt using your steering wheel controls—no screens, no distractions. Save your family's funniest answers, mark favorites, and turn your next road trip into a rolling connection factory.