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101 Money-Themed Would You Rather Questions for Middle School Students (Free PDF)

Increase student engagement and fun by introducing these money-themed Would You Rather questions for middle school students.

Looking for something fun for your middle school students?

middle school students at desk working, text overlay, "101 Would you Rather Questions about Money for Middle School Students"

These Would You Rather middle school questions are money-themed, and would be great for:

  • Opening to a financial literacy course
  • Closing to a financial literacy course
  • Early finishers
  • Bellringers
  • Just having fun

Ready for some killer This or That money-themed questions that will help engage your students around the topic of money?

Would You Rather Questions for Middle School Students

Maybe you’ve got early finishers who need something to do, or you’re looking for a way to keep students engaged while you teach financial literacy.

Use these money-themed Would You Rather questions for your middle school students in a variety of different ways!

Would you rather (choose This or That)…:

1. Get a quarter, or get two dimes and a nickel?

2. Go into a bank to get the money that you need from your account, or use an ATM to get the money you need from your account?

3. Be awesome at counting money, or be awesome at inventing things?

4. See the $2.00 bill in circulation again, or see the $0.20 coin in circulation again?

5. Go on a $10 shopping spree at the Dollar Tree, or go on a $10 shopping spree at Walmart?

6. Have money that changes color with your mood, or money that is magnetic?

7. Get paid to clean the toilets in your house, or get paid to mow the lawn? 

8. Keep your money in a piggy bank, or keep your money in a savings account at the bank?

9. Buy all the vending machine snacks you want each week over the next three months, or save that money and be able to buy a video game three months from now?

10. Ask questions you have about money, or ask questions you have about words you don’t know the meaning of?

11. Buy something online, or buy something in an actual store?

12. Do your own store transaction, or have your parents do your store transaction for you?

13. Be able to make in-app purchases that you want, or be able to drive yourself to wherever you want to go?

14. Buy your family holiday presents with your own money, or buy them birthday presents with your own money?

15. Spend $35 buying a product from a brand that you love, or spend $35 investing in a stock in that brand?

16. Receive money as a gift, or receive an item that you want as a gift?

17. Explain how money works to an alien, or explain how to skateboard to an alien?

18. Buy a bag of chips two days/week for the next three months, or buy something for $50 in 3 months from now?

19. Carry around cash in your wallet/purse all the time, or carry around cash just when you go to purchase something at a store?

20. Use coins to make exact change when you purchase something, or pay by rounding to the next dollar up (and get change back)? 

21. Spend lunch with Elon Musk, or Warren Buffett?

22. Pull weeds for extra cash in the summer, or start a business for extra cash in the summer?  

23. Spend $50 now to buy all the snacks you want from Costco for the next 3 months at a 10% discount, or buy it in smaller quantities as you want it, without the discount?

24. Save your money for the next six months to be able to pay cash for a concert you really want to go to, or owe your parents $150 and go this month?

25. Buy an $11.50 movie ticket for a movie with friends this weekend, or spend $19.99/month to see all the movies you’d like to each month?

26. Owe your friend money, or owe your parents money?

27. Own a pet, or own a new bicycle?

28. Buy new sports equipment for your first season, or buy used sports equipment at a discount for your first season?

29. Watch a documentary about money, or read a book about money?

30. Eat your lunch packed from home, or buy lunch from the cafeteria?

31. Invest $50 in a stock of a brand you recognize and love, or buy a product from that same brand you recognize and love?

32. Pay a late-fee on library books, or pay an extra monthly cost on an app subscription you forgot to cancel?

33. Buy a new video game, or buy a used video game?  

34. Read a book titled “How to Make $500 in 90 Days”, or read a book titled “How to Become a Ninja-Level Saver (and Save $500 in 90 Days)”?

35. Pay $65 to own a metal detector you want to use once, or rent a metal detector at a $19.99 rental fee?

36. Use your money to buy an item (candy, a book, video game, etc.), or use your money to experience something (a movie ticket, ride at the fair, summer camp, etc.)?

37. Understand how to make change, or understand compound interest?

38. Get an allowance, or get paid to do chores?

39. Go back in time and buy 10 beanie babies in the 1990s (at a cost of about $50), or have that same $50 now, but not the beanie babies?

40. Pay no sales tax for the rest of your life, or pay no late fees for the rest of your life?

41. Be able to double your money in 30 days, or get $15 right now?

42. Stop buying snacks, or stop buying in-app purchases?

43. Lose two dimes and a quarter, or lose a dollar bill?

44. Have unlimited time, or have unlimited money?

45. Never be able to buy something at a store again, or never be able to buy something online again?

46. Work at a job indoors year-round, or work at a job outdoors year-round?

47. Pay for someone to clean your room, or pay for someone to drive you everywhere in a sports car?

48. Skip buying snacks for a whole month, or skip buying anything from your favorite store for a whole month? 

49. Travel back in time to the Civil War with the money you have right now, or travel to 60 years in the future to use the money you have now?

50. Pay $20 for an in-person hobby class (like crafts, yoga, karate, etc.), or pay $20/month for unlimited hobby classes online you take in your own home?  

51. Be really good at saving money, or be really good at earning money?

52. Work for your parents around the house in the summer, or get a job helping neighbors in the summer?

53. Win the lottery and announce that you are the winner, or win the lottery and remain anonymous (keep your name a secret)?

54. Donate money to an animal shelter, or donate money to a homeless shelter?

55. Get a gift card to Nike for $50, or get a gift card to Barnes & Noble for $50?

56. Win 10,000 Starbucks reward stars, or win $100?

57. Win a free, 1-week homework pass, or win $25?

58. Carry around coins in your wallet, or just carry around bills ($1, $5, $10, etc.)?

59. Start collecting coins, or start collecting Happy Meal toys?

60. Be stuck on a desert island with $20,000, or be stuck on a desert island with 5 years’ worth of food?

61. Get a $25 gift card to Walmart, or get $25 in cash?

62. Swim in a pool full of coins, or swim in a pool full of dollar bills?

63. Use your money to buy a gift for your friend, or use your money to donate to a cause you find important?

64. Pay for one ticket for an amusement park that gets you into every ride ($36.00), or pay for each individual ride you want (at $3.00 each)?

65. Use a savings account to store your money, or use a piggy bank to store your money?

66. Use the swim suit/swim trunks from last season that still fit you, or pay for a new pair?

67. Make a list/write down what you want to buy before you go shopping, or wing it and buy as you want things?

68. Supersize your fast-food order for an extra $2.00, or order the normal size and use that $2.00 in another way?

69. Spend your money at the grocery store, or spend your money at a Target?  

70. Save up a year to have dinner with the Disney princesses at Cinderella’s Royal Table, or save up a year and buy all the Disney merchandise (shirts, toys, DVDs, etc.) you want?

71. Pay for snacks at the movie theater, or eat a snack at home before leaving for the movies? 

72. Go to a mall to walk around when you don’t have any money to spend, or go to a park to play when you don’t have any money to spend?

73. Money be green and white like it is now, or money be different shades of purple? 

74. Your family spend money to go on 3 weekend trips throughout the year, or your family spend money to go on one longer trip for a week, once per year?

75. Learn how to cook your own food, or learn how to make your own clothes?

76. Be given $10 now, or be given $20 two months from now (with the possibility that you would be given $0 if you wait)?

77. Open a lemonade stand for extra money, or open a hot cocoa stand for extra money?

78. Have your allowance doubled, or receive twice as much next birthday in cash as you did last year?

79. Attempt to win prize money by going on a game show, or attempt to win prize money by playing the lottery?

80. Let cameramen film your life for 60 hours/week and show it as a reality TV show for $20,000/year to start, or keep your privacy?

81. Earn $20 to spend the night in a rumored haunted house, or earn $20 cleaning public restrooms for two hours?

82. Give back everything you purchased last month and get your money back for all of it, or keep what you purchased last month and not get back the money?

83. Know how much money your parents make in a year, or know how much money your principal makes in a year?

84. Own a magical printer that prints out real money, or have all of your problems magically disappear?

85. Own $5,000 in land, or own $5,000 in gold coins?

86. Have to pay for your own school clothes, or have to pay for your own summer camps?

87. Get to decide what job you have when you grow up, or get to decide where you live?

88. Grow $20 in your backyard, or get the job of your dreams upon graduating?

89. Take a field trip to a U.S. Mint, or take a field trip to a bank?

90. Earn $20/hour, or earn a $50,000 annual salary?    

91. Print out all the sheets you want in black and white for $0.20/page, or print out all the sheets you want in color for $0.69/page?

92. Sell tee-shirts with funny messages on them, or sell mugs with funny messages on them?

93. Have a birthday party at an event location (bowling, arcade, etc.), or have a birthday party at home with friends (sleepover, day party, etc.)?

94. Pay $3 each time you want a cake pop, or spend $35 taking a class to learn how (plus supplies when you want to bake your own)?

95. Add an engine to your bike so that you can get around faster, or add an engine to your sneakers to get around faster?

96. Get paid to play video games, or get paid to act on a stage?

97. Catch your meals by fishing several times a week, or buy your meals from a grocery store?

98. Save money by wearing last year’s clothes (that still fit) one more year, or save money by unsubscribing to all streaming services (Netflix, Hulu, Amazon, etc.)?

99. Be known for being able to find a good deal (coupons, sales, etc.), or be known for being on a TV show?

100. Get paid in gems, or get paid in money?

101. Pay for the $5.00/month insurance on your new computer, or pay for a new computer to replace your current one if it breaks/when it wears out?

I'd love to hear what discussion starts and what answers your students give to these Would You Rather questions for middle school. Share in the comments below!

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Amanda L. Grossman is a writer and Certified Financial Education Instructor, a 2017 Plutus Foundation Grant Recipient, and founder of Money Prodigy. Her money work has been featured on Experian, GoBankingRates, PT Money,, Rockstar Finance, the Houston Chronicle, and Colonial Life. Amanda is the founder and CEO of Frugal Confessions, LLC. Read more here or on LinkedIn.