150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (2024)

Last Updated on March 3, 2024

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‘This or That’ is an exciting game that you can play with your friends, relatives, and even coworkers to get to know them better. The game can also help to keep the conversation going, especially when you’re out on a date but seem to be running out of ideas.

‘This or That’ is closely related to the classic game of ‘Would You Rather.’ To play either game, you’ll need to come up with a set of questions as well as a list of players to answer those questions.

The unwritten rule is that the questions should be as unique or outrageous as possible so that you can uncover certain details about the players that you don’t already know. And to make the game even more lively, the participants might consider switching roles. For instance, you can have an arrangement where everyone takes turn to ask their round of ten questions.

But besides their similarities, ‘This or That’ and ‘Would You Rather’ also have glaring differences. Most notably, ‘Would You Rather’ questions are usually complete sentences, whereas ‘This or That’ questions tend to be relatively short phrases of about 3 to 7 words.

Another difference between these two fun party games is that ‘Would You Rather’ often offers the participants a chance to choose between two bad things. Therefore, they have to settle for the lesser evil, so to speak. With most ‘This or That’ questions, the options presented are usually things that the participants find acceptable. But they have to choose which one they’d love the most.

Read on for a detailed list of some of the most challenging ideas for your next ‘This or That’ game.

How to Choose the Best ‘This or That’ Questions

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (1)

As we’ve already indicated, the primary consideration when choosing ‘This or That’ questions is that the questions should be unique and if possible, a bit outrageous. You don’t want to pose a question whose answer you already know. For instance, it would make no sense asking your friend whether they prefer Trump or Biden if you already know which political party they’re affiliated with.

Another crucial factor when choosing ‘This or That’ questions is that the audience should have some familiarity with the subject. In essence, the questions asked should be relevant to the audience. Asking an 8-year old if they’d prefer Mars or Earth is a waste of time as they’re likely not already acquainted with the solar system.

Last but not least, go for fun questions that also allow you to find out more about the participants. That’s particularly true if you’re playing ‘This or That’ with a love interest. It’s an easier way of finding out what their hobbies and interests are. And in most cases, they’ll answer simply and honestly, as opposed to if the questions were framed the usual way.

‘This or That’ Questions on Hobbies and Personal Interests

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (2)

1. Arctic or dessert?
2. Beach or forest?
3. City streets or country trails?
4. Comedy or romance?
5. Dancing or singing?
6. Dine-in or delivery?
7. Facebook or Twitter?
8. Flying or driving?
9. Fruits or vegetables?
10. Horror or comedy?
11. Hunting or fishing?
12. Movie or music?
13. Oceans or mountains?
14. Piano or guitar?
15. Road trip or game drive?
16. Tea or soda?
17. Theme Park or Water Park?
18. Vacation or staycation
19. Video games or board games?
20. Wine or beer?

‘This or That’ Questions on Personal Appearance

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (3)

1. Abs or chest?
2. Bare feet or shoes?
3. Beard or mustache?
4. Black or red?
5. Black or white?
6. Blondes or brunettes?
7. Boots or sandals?
8. Boxers or briefs?
9. Bracelet or necklace?
10. Buttons or snaps?
11. Checks or stripes?
12. Curved hips or big boobs?
13. Dress or pants?
14. Dress or skirts?
15. Facial hair or clean-shaven?
16. Heels or flats?
17. Long hair or short hair?
18. Long-sleeved or short-sleeved?
19. Perfect teeth or perfect hair?
20. Pierced or clip-on?
21. Piercings or tattoos?
22. Purple or green?
23. Shorts or pants?
24. Smile or eyes?
25. Sweater or jacket?
26. Tall or short?
27. Tan or pale?
28. Toothpaste or deodorant?
29. Underdressed or overdressed?
30. Yellow or orange?

‘This or That’ Questions for Children and Teens

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (4)

1. Mom or dad?
2. Sister or brother?
3. Uncle or aunt?
4. Grandpa or grandma?
5. Addition or subtraction?
6. Multiplication or division?
7. Cat or dog?
8. Cowboys or aliens?
9. Fair or theme park?
10. French or Spanish?
11. Hide-and-seek or obstacle course?
12. History or English?
13. Home alone or grounded at school?
14. Jam or jelly?
15. Jokes or riddles?
16. Numbers or letters?
17. Saturdays or Sundays?
18. Teacher or parent?
19. Toys or video games?
20. Walk or skip?

Challenging ‘This or That’ Questions

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (5)

1. Asking questions or answering questions?
2. Badly wounded or chronically ill?
3. Early bird or night owl?
4. Fame or fortune?
5. Locked or unlocked?
6. Lose your sight or lose your hearing?
7. Love or money?
8. Money or intelligence?
9. Permission or forgiveness?
10. Riches or happiness?
11. Secretive or open?
12. Smart or beautiful?
13. Touch or taste?
14. Truth or dare?
15. Younger or older?

Adult and Dirty ‘This or That’ Questions

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (6)

1. Call or text?
2. Group wedding or group sex?
3. Marriage or career?
4. Marriage or children?
5. Roses or Lilies?
6. Serious or funny?
7. Smoke or drink?
8. Boobs or butts?
9. Hugs or kisses?
10. Legs or thighs?
11. Licking or sucking?
12. Sex in the car or in the hallway?
13. Sex on the first date or on the first day at school?
14. Sex or cuddling?
15. Sex with your crush or with your ex?

Preparing for the Ultimate ‘This or That’ Marathon

So, you know how the game goes now. You have played it enough times with your friends that there is not much that anyone can say that will throw you off or shock you. Its time to make things interesting. Below, we are including the ultimate 50 ‘This or That’ questions that you can ask the next time you have friends over. We won’t make it all PG-13, we will keep it light and friendly too, but using these questions is the best way to get to know those closest to you a little better. And remember, if they answer, they have to say why!

  • Bad haircut or bad dye job?
  • Winning the lottery or finding your soulmate?
  • Phone in bathroom or no phone in bathroom?
  • Comedian in serious film or serious actor in comedy film?
  • A store where every item is free or a restaurant where every dish is calorie free?
  • Babies dressed as animals or animals dressed as humans?
  • Rich and famous or rich and unknown?
  • Cooking or being cooked for?
  • Hang out with little kids or old folks?
  • Reality shows or documentaries?
  • Call first thing in the morning or call in the middle of the night?
  • Take a friend on your family vacation or join a friend on their family vacation?
  • Shopping online or shopping in-store?
  • Start assignments immediately or wait until the last minute?
  • Teacher reads your text message aloud or teacher tells the whole class your grade?
  • Drive to school or take the bus?
  • Win the lottery or land your dream job?
  • Video meetings or in-person meetings?
  • Work from the office or work from home?
  • Team building after work or team building on the weekend?
  • Smartest person in the world or richest person in the world?
  • See the future or change the past?
  • Growth or security?
  • Money or love?
  • Misunderstood after death or forgotten after death?
  • Massive success by accident or modest success on purpose?
  • Free travel for one year or free lodging for five years?
  • Second chance at love or second chance for your career?
  • Sleeping with the bedroom door closed or open?
  • Toilet paper over or under?
  • Wash dishes immediately or wait until the sink is full?
  • Clean a litter box or walk a dog?
  • Ancient Rome or Ancient Greece?
  • Black coffee or sugar and cream?
  • Reading a book or listening to an audiobook?
  • Live with your parents or grandparents?
  • Swimming in a pool or swimming in the sea?
  • Mom scolding you in public or dad not talking to you?
  • Superpower of invisibility or ultimate strength?
  • Rich and few friends or poor and more friends?
  • Live without stylish outfits or life without a mobile?
  • Spend life in a village with no Internet or live in a city with unlimited Internet?
  • Have peace in life or save the world from global warming?
  • Wrestle naked in a pool of Jell-O or chocolate pudding?
  • Make out at the movies or in the back seat of my car?
  • Lose your sense of feeling during love or lose your sense of taste?
  • Take a body shot off of me, or have me take a body shot off of you?
  • Sweat profusely in the bedroom or have insatiable dry-mouth?
  • Walk-in on your best friend naked, or have your best friend walk in on you naked?
  • Have a naked picture of you become an internet meme, or be caught on camera naked during a live newscast?

Icebreakers to Ease the Tension

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (7)

Let’s say you are playing ‘this or that with a group of new people, and you don’t really know each other, sometimes it can be best to do an icebreaker or two in order to get everyone feeling a little more comfortable with one another. Here are 10 fun icebreaker questions that you can use at the start of a ‘this or that’ marathon to ease any tension and get everyone in the mood for spilling their darkest secrets:

  1. What celebrity do most people say you look like?
  2. Pull out your phone; what is your most used emoji?
  3. What is the best thing you have bought so far this year?
  4. What bucket list item do you most want to check off in the next six months?
  5. Imagine you can instantly learn any language. Which would you choose?
  6. Choose one famous person from history you want on your team during a zombie apocalypse.
  7. Would you want to have an imaginary friend today? Did you have one as a child?
  8. Which superpower would you give to your arch enemy?
  9. What is something interesting we would not know about you just by looking?
  10. Which show do you remember most from your childhood?

‘Would You Rather’ Mix things up?

Sometimes, ‘this or that’ might not be the game to fit the vibe, but just by mentioning a game of ‘would you rather’. everyone gets excited. (News flash: they’re really really similar). Anyway, here are 20 ‘Would You Rather Questions’ that you can ask in case you are called upon to play:

  1. Would you rather lose your ability to speak or the ability to hear for your entire life?
  2. Would you rather work more hours a day, but have longer weekends or work fewer hours a day with more workdays?
  3. Would you rather talk like Yoda or breathe like Darth Vader for the rest of your life?
  4. Would you rather be insulted by Gordon Ramsay for 10 seconds or receive unlimited text messages from Donald Trump for 10 days?
  5. Would you rather be a clown who distracts the bull or the cowboy who rides the bull?
  6. Would you rather drink water from a vase that has 2-week old flowers, or eat a giant 3-foot spiderweb?
  7. Would you rather pee through your mouth every time or have your best friend pee into your mouth one time?
  8. Would you rather lose all of the money you’ve earned this year or lose all of the memories you’ve gained this year?
  9. Would you rather ace a job interview at your dream job or go on a date with the hottest person you know?
  10. Would you rather live in a real haunted house or in the middle of a dessert?
  11. Would you rather master a musical instrument or have a photographic memory?
  12. Would you rather be attacked by an insane murderer or be given a million dollars every day for the rest of your life?
  13. Would you rather have 10,000 spoons when all you need is a knife or always have a knife but never be able to use spoons?
  14. Would you rather have small bad things happen to you for a month or one bad thing happen to you?
  15. Would you rather do something you love and make just enough money to get by or do something you hate but make billions of dollars?
  16. Would you rather have a 10-hour dinner with a headstrong politician from an opposing party, or attend a 10-hour concert for a music group you detest?
  17. Would you rather go to a bar, a club, a house party for a good time, or just stay home for quiet TV dinners?
  18. Would you rather work a morally questionable job that makes a lot of money or a job that helps a lot of people but doesn’t make much money?
  19. Would you rather make a huge salary but have to give everything above minimum wage to charity, or have a mid-range salary and be able to spend it on whatever you want?
  20. If you were responsible for choosing whether the world would have bagels or doughnuts, which one would you choose?

Wrap Up

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (8)

As you may have noticed from the list above, ‘This or That’ questions generally fall under specific categories. That underscores the importance of selecting questions that are relevant to your audience.

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (9)
Posted by:Igor Ovsyannnykov

Igor is an SEO specialist, designer, photographer, writer and music producer. He believes that knowledge can change the world and be used to inspire and empower young people to build the life of their dreams.When he is not writing in his favorite coffee shop, Igor spends most of his time reading books, taking photos, producing house music, and learning about cinematography. He is a sucker for good coffee, Indian food, and video games.

150+ Extremely Challenging and Hilarious ‘This or That’ Questions | Inspirationfeed (2024)


What is the best question for this or that? ›

This or That Questions for Students
  • Be best friends with Batman or Superman?
  • School start and end earlier or start and end later?
  • Go on a field trip to the zoo or to a museum?
  • Have a longer lunch or a longer recess?
  • Go to prom or go to homecoming?
  • Write a story or a write a poem?
  • Be good at sports or get good grades?

What are some super hard questions? ›

14 Tough Questions Answered
  • Why are there wars? ...
  • Why do spouses divorce? ...
  • Who decides which of the divorced parents their children will live with? ...
  • Why do people have to grow old? ...
  • Why do people have to die? ...
  • What happens when people die? ...
  • Does it hurt to die? ...
  • What do we do after a person dies?

What is 20 questions challenge? ›

20Q asks the player to think of something and will then try to guess what they are thinking of with twenty yes-or-no questions. If it fails to guess in 20 questions, it will ask an additional 5 questions. If it fails to guess even with 25 (or 30) questions, the player is declared the winner.

What's an icebreaker question? ›

Icebreaker questions for small groups

What question do you wish people would ask you? What is one thing we would never guess about you? What's one thing you want to do in life but don't know where to start?

What would you rather adult questions? ›

Hard Would You Rather Questions

Would you rather walk in on your parents having sex or have them walk in on you having sex? Would you rather be stuck in a phone box with ten snakes or ten tarantulas? Would you rather say your ex's name during sex or your partner's best friend's name?

Would you rather questions flirty? ›

Flirty “Would you rather?” questions for texting fun throughout the day
  • Would you rather have a sexy shower or a sexy bath?
  • Would you rather have long, slow sex or a quickie?
  • Would you rather have everyone you know be able to read your thoughts or everyone you know have access to your internet history?

What's a super deep question? ›

A deep question is one that invites people to share their core values and what truly matters to them. An example of a deep question could be: “What do you think is the most important thing in life, and why?

What are 10 good questions? ›

What are 10 good questions to ask someone?
  • What's your favorite childhood memory?
  • What's your favorite movie and why?
  • What was your worst date?
  • What was your favorite subject in school?
  • What do you enjoy doing in your free time?
  • What's your favorite family holiday tradition?
  • What's your favorite family recipe?

What are the most unusual questions? ›

110 Kinda Weird Questions To Ask Someone To Get To Know Them Better
  • Have you ever eaten something from off the floor?
  • What would 10-year-old you think of you now? ...
  • Do you ever talk to yourself?
  • Do you know how to whistle?
  • What's your favorite smell? ...
  • Do you prefer dogs or cats?
Aug 29, 2022

What are the top five powerful questions? ›

5 Powerful Questions Every People Manager Needs to Know and Use
  • What do you think? Not rocket science is it? ...
  • What makes you think this? ...
  • Can you tell me more? ...
  • How can I support you with this? ...
  • What do you think are the next steps?

What are some hard hitting questions? ›

Hard questions to ask friends
  • What is the relationship with your parents like?
  • What is your worst memory?
  • What fears do you experience?
  • What do you find most challenging in your life right now?
  • What is something that not many people know about you?
  • What prevents you from sharing that part of yourself?

What are some hard quiz questions? ›

Hard history quiz questions
  • What is Shakespeare's shortest play?
  • What is Prince William's full name?
  • What month of which year was the first iPhone released?
  • For two points, what were the most popular boys' and girls' names for 2019?
  • Who was the youngest British Prime Minister?
  • What year did Vincent Van Gogh die?
May 16, 2024

What are the thickest questions? ›

Thick Questions:
  • What if . . . ?
  • Why did . . . ?
  • How do you know . . . ?
  • What caused . . . ?
  • How can you prove . . . ?
  • Why do you think . . . ?
  • How can you support that?
  • Can you think of another way to . . .?
Nov 9, 2016

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