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101 Money-Themed Would You Rather Questions for Teen Students (Free Printable)

Use these Money-themed Would You Rather questions for high school students to get teens interested in money, and keep things fun.

One of the biggest struggles educators tell me about is keeping students engaged with financial literacy content.

teen students at desk smiling and talking, text overlay "101 Would You Rather Questions about money for high school students"

Which is exactly why I created these fun, teen-relevant, and thought-provoking Would You Rather questions for high school students all around the topic of money.

They’re great for:

  • Breaking the ice
  • Opening up debate and conversation
  • Learning about your own and someone else’s money values
  • As an opener for a fin lit course
  • Dinner table conversation

Ready for some killer this or that questions for teens that will get them engaged and thinking about money in different ways?

Would You Rather Questions for Teen Students (about Money)

When using these would you rather questions for students, your teens might:

  • Ask you if they can research to get more information
  • Weigh some pros and cons
  • Debate which situation would be worse, or which would be better
  • Get out their calculators
  • Wonder if it’s even possible
  • …and more!


Would you rather (choose This or That):

1. Get a $100 bill from the bank, or get 100, $1 bills from the bank?

2. Be awesome at picking stocks to invest in, or be awesome at inventing things?

3. See the $1,000 bill in circulation again, or see the $0.20 coin in circulation again?

4. Go on a $25 shopping spree at Walmart, or go on a $25 shopping spree at Nike?

5. Work a seasonal job for six months (12 hours/day, 7 days/week), or a year-round job for 8 hours/day with weekends off?

6. Own a car fueled by gasoline, or fueled by chocolate?

7. Own a 5-year-old car you bought with cash, or lease a brand-new car that you make payments on each month?

8. Have a conversation about money, or a have conversation about sports?

9. Buy something online, or in a store?

10. Pay for your next purchase with cash, or with a debit card?

11. Pay the bill on a date, or split the costs of your date with the other person?

12. Pay with a check, or pay with a debit card?

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

14. Explain how money works to an alien, or explain how to play baseball to an alien?

15. Buy a $5 Frappuccino two days/week for the next year, or buy something for $520 in 12 months from now?

16. Carry around cash in your wallet/purse, or go cashless and pay with a cash app?

17. Use coins to make exact change, or pay by rounding up to the next dollar? 

18. Make breakfast every morning and save lots of money, or run to Starbucks each morning?

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

20. Work on the weekends during the school year, or work during the summertime, only?

21. Spend $50 now to buy all the stationary you want for the next year at a 10% discount, or buy it in smaller quantities as you want it (without the discount)?

22. 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 friend $150 and go this month?

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

24. Own a house, or rent an apartment?

25. Buy new furniture for your first apartment, or buy used furniture for your first apartment?

26. Live with a roommate in your first apartment, or live alone in your first apartment?

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

28. Invest $50 in a stock of a brand you recognize, or invest $50 in a stock of a no-name brand that has strong earnings over the last few years?

29. Pay for the next six months’ auto insurance now and save $35, or pay for your auto insurance in installments each month for six months (without the discount)?

30. Read a book titled “How to Make $1,000 in 90 Days”, or read a book titled “How to Become a Ninja-Level Saver (and Save $1,000 in 90 Days)”?

31. Pay $250 to own a bicycle, or rent a bicycle whenever you need to for $20 each time?

32. Use your money to buy an item (shoes, book, video game, etc.), or use your money to experience something (movie ticket, ride at the fair, dance class, etc.)?

33. Buy really expensive sports equipment used at a discount, or buy less quality sports equipment brand new?

34. Understand how to invest in a stock, or understand compound interest?

35. Go back in time and buy 10 beanie babies in the 1990s (at a cost of about $50), or invest $50 in the stock market back in the 1990s?

36. Get a refund for a product you bought that breaks within 25 days of purchase, or not mess around with getting a refund on a broken product and just trash/recycle it?

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

38. Eat fast food half as often to save money, or stop buying any apps and any in-app purchases?

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

40. Have unlimited time, or have unlimited money?

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

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

43. Pay for a personal maid, or pay for a personal chef?

44. Pay for oil changes for the next 60+ years, or learn how to do your own oil changes and spend an estimated 1 hour + money on supplies to do it each time yourself?  

45. Eat beans and rice for every lunch and dinner for 2 weeks to get the new pair of sneakers you want, or eat what you would like and save the money up over the next 2 months?

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

47. Work for your parents around the house in the summer, or get a job somewhere else in the summer?

48. Win the lottery and announce that you are the winner, or win the lottery and remain anonymous?

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

50. Have a prepaid debit card loaded with $500 of your money, or have a credit card with a $3,000 limit? 

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

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

53. Retire from a satisfying job at 60, or retire from a satisfying job at 75?

54. Get the newest iPhone on a payment plan for the next 36 months, or keep your current phone and save up for a debt-free iPhone?

55. Move to a higher cost-of-living area (by 13%) for a $5,000 raise, or stay where you are?

56. Pay $995/month for your first apartment and live alone, or take on a roommate and pay $497.50/month?

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

58. Tip a waiter 20% even though the service wasn’t good, or pay a $15 late-fee penalty?

59. Drive 5 miles right now to return a dozen library books so that you don’t get charged a $0.60 fine, or return the dozen library books tomorrow and pay the fine?

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

61. Supersize your fast-food order each time for a total of an extra $50 over the next year, or order the normal size and use that $50 in other ways?

62. Save up for a year to go on a spring break trip to the beach with friends, or save up for a year and buy all the clothes you want?

63. Never be able to buy your own car, or never be able to buy your own home?  

64. Live at home for two years after graduating and save up enough money for a car, or live on your own right after graduating and ride a metro/bus/carpool for those two years?

65. Dollar bills be green and white like they are now, or dollar bills be different shades of purple? 

66. Spend money to go to the beach for a week, or spend money to go to the mountains for a week?

67. Work overtime each weekend for one month to afford something specific you want, or work your regular hours and take two months to save up for something specific you want?

68. Let your car amass tons of dirt and trash over a year and have it professionally cleaned for $75, or maintain your car by cleaning the trash and dirt out twice a month?

69. Not work during college and owe $20,000 in student loans when you graduate, or work a part-time job through college and owe half that ($10,000)?

70. Pay an expert $300 to do a custom paint job on your car, or pay someone who is still working on becoming an expert $50 to do the same work?

71. Attempt to win prize money on Survivor, or attempt to win prize money on Jeopardy?

72. 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?

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

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

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

76. Be paid the President of the United States’ salary, or be paid the average professional athlete’s salary

77. Have a checking and savings account, or keep all your money at home?

78. Be paid weekly from your job, or be paid bi-weekly from your job?

79. Be responsible for a closing shift at work, or be responsible for opening shift at work? 

80. Be responsible for paying for gas and car insurance, or ride the school bus and pay for public transportation as needed?

81. Spend a year doing non-profit work and gaining experience, or spend a year in school working towards a degree?

82. Get rid of the penny, or get rid of the $1 bill?

83. Earn 1.01% interest on your savings at a regular bank, or open an online savings account and earn 4.01% interest?

84. Apply for scholarships and grants to pay for college, which don’t need to be paid back, or take out loans for what you need (which do need to be paid back)?

85. Wait three weeks to get a book free through interlibrary loan that you really want to read, or buy the book right away for $19.95.

86. Get paid to never be on your smartphone again, or get paid to never watch TV again?

87. Get paid for a hobby that you love, or don’t get paid and just keep doing it because you like it?

88. Be in charge of paying for your pet’s costs, or be in charge of paying for the gas in your car?

89. Spend 2 Saturdays a month earning money, or spend those 2 Saturdays chilling out.

90. Collect some type of card in the hopes that they’ll increase in value over the years, or collect a certain brand of toy in the hopes that they’ll increase in value over the years?

91. Pay $1,000,000 to live in the International Space Station for a month, or pay $1,000,000 to live in the Aquarius Reef Base in the bottom of the ocean for a month?

92. Keep buying the newest and best smartphone, or keep buying the newest and best video game console?   

93. Stand in line overnight to be one of the first to buy the newest iPhone, or rest peacefully at night with the phone you have?

94. Buy a printer for just $40 where the ink cartridges cost $150 to replace, or buy a $150 printer where the ink cartridges cost just $40 to replace?

95. Have 2 fewer haircuts a year to save money, or use your backpack an extra year to save money?

96. Be known for having lots of money, or be known for having lots of great ideas?

97. Be famous and rich and everyone know it, be rich and no one know it?

98. Be alive during the Great Depression, or be alive during World War 2?

99. Do a no-spending challenge for a week (where you can’t spend any money for the week), or do a savings challenge for a month (where you try to reach a target savings amount in one months’ time)?

100. Still go out to eat but order an appetizer only (because that’s what you have money for), or just not go out to eat at all since you can’t afford to get an entrée?

101. Invite friends over to your house to save money while hanging out, or not hang out with friends when you don’t have money to spend?

I can't wait for you to hear the answers to these Would You Rather questions for students (AND, to see the discussion and debate that goes into why they chose the option they did!).

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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.