100 Would You Rather Questions for the Holidays 

The holidays — and their inevitable parties — usher in a season of group celebrations. If you want to spice up the conversations at your next gathering, try a few of these would-you-rather questions for any type of holiday event. 

Family Gatherings

1. Would you rather have to eat a whole turkey in one sitting or never be able to eat turkey again?
2. Would you rather get the best gift you ever received again or get a new gift (but have no idea if it will be good or bad)?
3. Would you rather relive a past winter holiday again or get to travel to a future winter holiday?
4. Would you rather spend the holidays with your family or with three celebrities (you can choose the celebrities)?
5. Would you rather have to cook the big holiday meal every year or have to clean up and do the dishes after the holiday meal every year?
6. Would you rather be a kid or a grandparent during the holidays?
7. Would you rather give up one family tradition or start a new one?
8. Would you rather have the (skill) of (family member) or the (another skill) of (another family member)?
9. Would you rather get to invent a holiday on whatever day you want or have a holiday fall on your birthday?
10. Would you rather eat Thanksgiving food every day or never again?

Company Parties

11. Would you rather work only on holidays (they are still holidays) or only get holidays off work?
12. Would you rather switch careers entirely or stay in your career field forever?
13. Would you rather wear a Santa outfit or an elf outfit to work every day for a month?
14. Would you rather be famous for starring in a cheesy holiday movie or not be famous at all?
15. Would you rather have an eggnog machine instead of a coffee machine at work year-round or have your corporate dress code require ugly Christmas sweaters?
16. Would you rather work untangling Christmas lights or work as a mall Santa?
17. Would you rather have "Dreidel, Dreidel, Dreidel" stuck in your head or "Jingle Bells?"
18. Would you rather get amazing presents for four nights of Hanukkah and bad presents for the other four nights, or get eight OK presents?
19. Would you rather your office always smelled like gravy or always smelled like turkey?  
20. Would you rather have your ears turn into elf ears or have a Santa beard forever?

Coordinate an office Thanksgiving potluck with a sign up. SAMPLE

Elementary/Middle School Class Parties

21. Would you rather give up Christmas trees or Christmas cookies?
22. Would you rather get one amazing holiday gift or 10 OK holiday gifts?
23. Would you rather have to eat 1,000 chocolate Hanukkah coins or eat just one — but with the wrapper still on?
24. Would you rather be an elf in Santa's shop or a reindeer on Santa's sleigh?
25. Would you rather have it be your favorite holiday every day or never have that holiday again?
26. Would you rather know what all your gifts are or be surprised by all your gifts?
27. Would you rather only have dessert on holidays or never have dessert on holidays?
28. Would you rather wash your hair with cranberry sauce or wash your hair with mashed potatoes and gravy?
29. Would you rather eat only Christmas cookies or only drink hot cocoa?
30. Would you rather be a turkey farmer or a pumpkin farmer?
    

Volunteer Appreciation Parties

31. Would you rather get a paper cut every time you wrap a Hanukkah present or get burned every time you light the menorah?
32. Would you rather have holiday decorations up all year or never be able to put them up again?
33. Would you rather volunteer to make 1,000 Christmas cookies or volunteer to decorate 100 Christmas trees?
34. Would you rather have to dress up every Hanukkah in a human dreidel or a human menorah costume?
35. Would you rather volunteer to help a friend wrap presents or shop for presents?
36. Would you rather eat candy corn every day or eat candy canes every day?
37. Would you rather volunteer as a mall Santa or in a live nativity with livestock?
38. Would you rather the holiday season start in August or not start until the first day of December?
39. Would you rather only be able to decorate with ugly holiday decorations or never have holiday decorations again?
40. Would you rather have your hair be tinsel or be bald?

Church & Temple Youth Groups

41. Would you rather wear an embarrassing outfit on TV in the Macy's Thanksgiving Day Parade or never be able to watch the Macy's Thanksgiving Day parade again?
42. Would you rather never listen to holiday music again or have to listen to your least favorite holiday song 10 times every single day (but after that you can listen to whatever you want)?
43. Would you rather lose your voice for the holidays or only be able to speak in lyrics from popular holiday songs?
44. Would you rather have to wear a Santa costume to school or an elf costume?
45. Would you rather only be able to eat latke or never eat latke again?
46. Would you rather have no Winter Break or have no Spring Break?
47. Would you rather win a gingerbread house-building contest or win a cookie-baking contest?
48. Would you rather have to do Hanukkah or Christmas-themed improv in front of the youth group or sing holiday songs in front of the youth group?
49. Would you rather have to sing Jingle Bells non-stop for 24 hours or not celebrate Hanukkah/Christmas this year?
50. Would you rather get a useful gift or a fun gift?

Groups of Friends

51. Would you rather get a person who is really hard to shop for during Secret Santa or have no one get your name for Secret Santa?
52. Would you rather live in a gingerbread house with your group of friends or never be able to live with any of them?
53. Would you rather experience a Christmas in 1700 or in 2100?
54. Would you rather spend Christmas with your group of friends or have them each be replaced by their favorite celebrity?
55. Would you rather only be able to watch your favorite TV show during the holidays or have to watch it every day of the year?
56. Would you rather star on a popular holiday music single or star in a popular holiday movie?
57. Would you rather lose all your money playing dreidel spin with your group of friends or replace your pillow with one made of latke?
58. Would you rather vacation somewhere cold or hot during the holidays?
59. Would you rather visit far-away family or far-away friends?
60. Would you rather get stuck in an airport during Christmas or get lost in a Christmas tree farm?

Host a Friendsgiving dinner with a sign up. SAMPLE

Nonprofits

61. Would you rather have people donate money or time during the holidays?
62. Would you rather always know what the perfect gift for someone else is or always get the perfect gift from others?
63. Would you rather have the winter holidays or summer months be the busiest time of the year?
64. Would you rather have too many volunteers or too many resources for the holiday season?
65. Would you rather be short on volunteers or accidentally schedule way too many at the same time?
66. Would you rather not send out your Christmas cards or only send them out two months too early?
67. Would you rather have an event that was turkey-themed or one that was eggnog-themed?
68. Would you rather have someone do something kind for you but have it stay anonymous or do it but you know who they are?
69. Would you rather host a 24-hour telethon or a 24-hour dance marathon?
70. Would you rather have full attendance at all your events or have full volunteers at all your events?

Church & Temple Small Groups

71. Would you rather go to a fancy holiday party or a homey one?
72. Would you rather never have snacks at small group or never have coffee at small group?
73. Would you rather eat a bowl of something icky for a church/temple holiday skit or sing in front of your church/temple at a holiday service?
74. Would you rather spend a discussion only speaking in original rhymes or spend a discussion only speaking in popular song lyrics?
75. Would you rather your house be clean or have a good meal?
76. Would you rather experience the first Christmas but as a donkey/livestock or not get to experience it at all?
77. Would you rather pull an all-nighter without coffee or forget an important holiday event that you were supposed to show up to?
78. Would you rather volunteer in kids' ministry or volunteer on the parking/seating team?
79. Would you rather only sing holiday music at your church/temple year-round but you don't have to lead it or lead it and sing normal worship songs?
80. Would you rather wear matching ugly holiday sweaters with your small group to your church's big holiday service or wear the same outfit to church/temple for a month, but it can be whatever you want?

Organize a holiday cookie exchange with a sign up. SAMPLE

Sports Teams

81. Would you rather have to pull Santa's sleigh for workouts or lift pumpkins?
82. Would you rather your uniforms look like Santa outfits or look like reindeer outfits?
83. Would you rather have everyone on your team be elf-sized and you be normal or have everyone be normal and you be elf-sized?
84. Would you rather eat a whole turkey before practice or have to drink gravy instead of water?
85. Would you rather replace your field with tinsel or pine needles?
86. Would you rather sweat gravy or sweat mashed potatoes?
87. Would you rather your team mascot be a turkey or a reindeer?
88. Would you rather replace your ball with a pumpkin or eat 100 gold Hanukkah coins before every game?
89. Would you rather play in the snow or in windy cold?

Any & Everyone

90. Would you rather have to put up outdoor Christmas lights for all your neighbors or wrap all the holiday presents for extended family members?
91. Would you rather have Thanksgiving at the White House or with your family?
92. Would you rather travel during the holidays or stay home?
93. Would you rather have snow every day during the holiday season or not have any snow at all?
94. Would you rather wear light-up Christmas lights or wear a red nose every day during the holiday season?
95. Would you rather spend a long time finding the best deal on a gift or spend more money but only shop for a small amount of time?
96. Would you rather eat only holiday food or watch only holiday movies?
97. Would you rather have a holiday party every night or no holiday parties to attend?
98. Would you rather only eat fruitcake for holiday desserts or not have dessert at all?
99. Would you rather have all your presents wrapped terribly or not have them wrapped at all?
100. Would you rather have an entire snow week off from school or an extra week of summer vacation?

Now no matter what group of people you're spending the holiday season with, you'll be sure to have lots of silly scenarios to talk about! 

Kayla Rutledge is a college student who spends most of her time writing, singing for her church and eating quesadillas. 

Related Articles

Class Party Ideas to Celebrate the End of School

30 Fun Facts About Easter