100 Extremely Challenging and Hilarious ‘This or That’ Questions

Last Updated on October 6, 2021

‘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

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

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

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

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

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

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?

Wrap Up

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.

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