200+ Best What If Questions to Ask Friends or Coworkers

This is our big list of what if questions to ask anyone.

What if questions are hypothetical questions that gauge folks’ responses to a variety of different scenarios. For example, “what if real life were more like the movies?” or “what if computers suddenly stopped working?” The purpose of these games is to help players sharpen critical thinking skills and to share their logic with the group so that others can understand them better. These prompts are also known as “what would you do if questions” or “hypothetical scenarios”.

What if is a type of question game, icebreaker game, and get to know you game. These prompts are similar to Would You Rather questions.

This list includes:

• what if question generator
• funny what if questions
• deep what if questions
• random what if questions
• good what if questions for work
• what if questions for friends
• what if questions for adults
• what if questions for couples
• what if questions for students

Here we go!

What if question generator

Here is a what if question generator to help you come up with hypothetical conversation starters.

Funny what if questions

1. What if every time you tried to use your smartphone, it took an unflattering selfie and sent it to all your contacts?
2. What if you could only communicate by breaking out into song?
3. What if you could play the perfect prank?
4. What if you could teleport, but you would arrive naked?
5. What if you had the power to temporarily mute people in real life?
6. What if you were put in charge of minorly inconveniencing all of the jerks of the world?
7. What if food could talk?
8. What if you were the PR person for a supervillain and had to rehabilitate their public image?
9. What if a red button that read “push me, I dare you” suddenly appeared in the middle of your living room?
10. What if a dramatic voice followed you around narrating your life?
11. What if real life were more like the movies?
12. What if you had to wear a dinosaur costume to one major life event?
13. What if you had to convince someone that you were actually your own identical twin?
14. What if you could only speak in questions?
15. What if your most ridiculous childhood fear was suddenly a valid concern?
16. What if woodland animals helped you with your everyday routine?
17. What if you were offered a free car, but it was covered in embarrassing photos of you and you couldn’t change the appearance?
18. What if a celebrity started coming to you for advice?
19. What if your twelve year old self wrote your dating profile?
20. What if you went on a date with someone who told you they exclusively listened to elevator music?
21. What if you could make one gross habit socially acceptable?
22. What if you could insult one famous figure from history?
23. What if you were the subject of a comedy roast and you could choose your roasters from anyone who has ever lived?
24. What if you had to choose someone to go on a date with based only on their internet search history?
25. What if you never had to go to the bathroom again?
26. What if you could take a pill to make flatulence smell like any more pleasant scent?
27. What if you peed your pants every time someone made you laugh?

Deep what if questions

1. What if you could travel back in time and give one warning to any individual?
2. What if you found out that you were at the center of a Truman Show-type scenario, and you were the main character of an elaborate reality show and everyone else in your life was an actor?
3. What if you had to choose between saving one family member or ten strangers?
4. What if you could learn the answer to just one secret of life?
5. What if you found out that someone you loved had committed a terrible crime?
6. What if you had the chance to change one event in history, but you wouldn’t know what the consequences of the change would be beforehand?
7. What if you could live forever?
8. What if you found out that life was just a simulation?
9. What if you could speak to one deceased loved one?
10. What if you could live from the perspective from one other person for one year?
11. What if you woke up as an eighteen year old with all the knowledge you currently have?
12. What if you could re-watch one single day from your life?
13. What if you could do one thing with a 0% chance of failure?
14. What if you could take a serum that would block fear forever?
15. What if you could preserve your consciousness in a computer?
16. What if you could erase other people’s memories?
17. What if you could send one message to a loved one after you die?
18. What if you found out that you had said something to hurt someone years after the fact?
19. What if you could ask anyone for one piece of advice?
20. What if you could change one thing about yourself?
21. What if you knew something terrible was going to happen to someone you cared about and you could not do anything to change it?
22. What if you were allowed to choose one thing to be reincarnated into?
23. What if you could know the worst thing that somebody ever did just by touching their hand?
24. What if you could get a glimpse of the afterlife? Would you want to know what happens when we die?

Random what if questions

1. What if you could talk to animals?
2. What if you knew tomorrow’s news before it happened?
3. What if the president called you out of the blue?
4. What if you found out a friend wrote a book and based a character off of you?
5. What if you had to suddenly fake your death and enter witness protection?
6. What if you won the lottery?
7. What if your best friend told you they had accepted a mission to colonize Mars?
8. What if you could open a museum on any subject?
9. What if you woke up and could speak in a totally different language?
10. What if you woke up in a different gender’s body?
11. What if you could suddenly only speak in gibberish?
12. What if you could fall asleep on command?
13. What if you could change the ending to one show or movie?
14. What if you could read a book from a different character’s perspective?
15. What if you could control the weather?
16. What if you had to pick one food to eat every day for the rest of your life?
17. What if you could only say ten words a day?
18. What if you could say one thing to the entire world?
19. What if you had to plan the perfect crime?
20. What if you were mistaken for a celebrity and expected to do their job?
21. What if you could fly?
22. What if you could shapeshift?
23. What if you could make one non-serious thing illegal?
24. What if you could win a lifetime supply of one product?
25. What if you received a message that read, “come find me– you know who”?
26. What if you could host your own talk show?
27. What if you had to swap bodies with one person? (Freaky Friday style)
28. What if you were hired to be a tester for one product?
29. What if a stranger approached you and whispered, “you are the chosen one?”

Good what if questions for work

1. What if computers suddenly stopped working?
2. What if your nemesis was hired at the company?
3. What if you were told that your new boss was a ten year old genius?
4. What if you saw a coworker updating their resume?
5. What if you were interviewing a candidate and they refused to speak?
6. What if you were interviewing a candidate and they handed you a portfolio full of plagarized versions of your work?
7. What if you could work from anywhere in the world?
8. What if the company let you choose your own working hours?
9. What if a client told you that they were thinking about switching to a competitor?
10. What if a client told you that they were going to leave because of something you did?
11. What if a coworker was not responding to your emails?
12. What if you were the boss for one day?
13. What if you could pick one perk to add to the compensation package?
14. What if you never had to go to another work meeting?
15. What if you never had to attend another Zoom call?
16. What if you found out your coworkers had all read your teenage diary?
17. What if you saw a coworker getting bullied at work?
18. What if you were put in charge of designing a new company logo?
19. What if you had to work with a clone of yourself?
20. What if you had to explain your job to a five year old?
21. What if a customer asked a question you did not know the answer to?
22. What if a coworker got promoted to a role that you were hoping to get?
23. What if you could pick the projects you work on?
24. What if you could hand pick your clients?
25. What if you had the power to rewind and re-do work conversations?
26. What if your manager gave you disappointing feedback?
27. What if a coworker regularly gave you criticism about your work?
28. What if you were put in charge of planning the office Christmas party?
29. What if you could pick one restaurant to open up a location next to your job?
30. What if you had to choose between being in the office full time or being remote full time?
31. What if you were the only one who showed up to work one day?
32. What if you could read your coworkers’ minds?

What if questions for friends

1. What if you had superpowers?
2. What if I moved away?
3. What if I suddenly disappeared without notice?
4. What if you hated my boyfriend or girlfriend?
5. What if you could find out every person who has ever had a crush on you?
6. What if we could communicate telepathically?
7. What if you found out I had accidentally spilled one of your secrets?
8. What if you learned I was a figment of your imagination?
9. What if one day I suddenly started speaking in a foreign accent?
10. What if I texted you “we need to talk…” What would your first instinct be?
11. What if your pet liked me better than you?
12. What if I said something that hurt your feelings?
13. What if I told you that your teasing hurt my feelings?
14. What if someone told you they had a crush on me?
15. What if someone said something unkind about me when I wasn’t around?
16. What if I snapped at you when I was having a bad day?
17. What if you could only take one form of transportation for the rest of your life?
18. What if today was the last time you would get to talk to me?
19. What if you had a machine that could print you any kind of food you wanted?
20. What if you had your own reality show? What would it be called and what would it be about?
21. What if you could never tell anyone that you loved them and could only show them?
22. What if you could design your own country?
23. What if you could instantly learn any skill?
24. What if you were put in charge of coordinating a group Halloween costume?
25. What if you could throw a party with an unlimited budget?
26. What if you could invent one thing?
27. What if you could de-invent one thing?
28. What if you could only watch one TV show for the rest of your life?
29. What if somebody offered you a million dollars to stay in a haunted house overnight?
30. What if I called you in the middle of the night?
31. What if I told you that I saw a ghost?
32. What if we had to fight off zombies together?
33. What if I was getting chased by an angry goose?
34. What if we could have a sleepover in any location you choose?
35. What if someone called and said I had put you down as a recommendation. What would you say?
36. What if I randomly started crying?
37. What if I randomly started laughing?
38. What if I tripped in public and fell down in front of a crowd of people?
39. What if you saw my face on a wanted poster?
40. What if I told you, “let’s get into some mischief”?
41. What if you found out that I had an evil twin?
42. What if I lost my memories?
43. What if you had to sum up our friendship in five words or less?

What if questions for adults

1. What if you did not have to work anymore?
2. What if you could have a conversation with your 5 year old self?
3. What if you could choose to forget certain memories?
4. What if you remembered everything since you were born?
5. What if you never had to sleep again?
6. What if you could choose one chore to get done by magic?
7. What if a stranger in a limousine handed you an envelope with $100,000 and drove away?
8. What if you had the opportunity to interview for your dream job?
9. What if you had the ability to psychically influence other people’s actions?
10. What if you could get a glimpse of twenty years in the future?
11. What if you had the energy of a ten year old?
12. What if you stopped physically aging?
13. What if you could instantly gain any one skill?
14. What if you could travel anywhere in the world, but you could not spend more than one year in the same place?
15. What if you could start a business?
16. What if you could guarantee that your kids would not make one particular mistake?
17. What if you had to start one new hobby. What would it be?
18. What if you had to compete in an athletic competition? What sport would you choose?
19. What if you could choose one age to stay indefinitely?
20. What if you had to have one song stuck in your head for an hour every day?
21. What if somebody offered you a free house but the walls were all see-through. Would you take it?
22. What if you could donate one million dollars to any one charity of your choice?
23. What if you could make one crime legal?
24. What if you could only watch one streaming service for the rest of your life?
25. What if you could un-do one purchase you made?
26. What if you could put one item into a time capsule for future generations to find?
27. What if you had to go without electricity for one year?
28. What if you could get rid of one profession permanently?
29. What if you could only see in black and white?
30. What if you had to give up one of your senses?
31. What if you could write your own epitaph?
32. What if you woke up in a time loop?

What if questions for couples

1. What if you found out I was secretly a spy?
2. What if your family didn’t like me?
3. What if your friends didn’t like me?
4. What if I forgot your birthday?
5. What if I got really sick?
6. What if I got a job on the other side of the country?
7. What if my ex showed up and tried to win back my love?
8. What if I developed an allergy to your favorite food?
9. What if you found out I hated your favorite movie?
10. What if our pet liked me more?
11. What if your future self sent you a message that we were going to one day break up?
12. What if you only had 24 hours to spend with me before going on a 5 year mission?
13. What if one of my friends started flirting with you?
14. What if you had to make me a present?
15. What if we had an argument and I didn’t say I was sorry first?
16. What if you found out I had dated a celebrity?
17. What if you found out that I secretly was a celebrity?
18. What if you found out that I was actually very wealthy?
19. What if you found out that I was in debt?
20. What if I wanted to save money and you wanted to spend it, or vice versa?
21. What if we had kids, and your parents tried to give parenting advice that clashed with our views?
22. What if I couldn’t decide what restaurant to eat at for dinner, no matter how many times you asked?
23. What if I did your pet peeve?
24. What if I gave you a present you didn’t like?
25. What if we could go on your dream date?

What if questions for students

1. What if you could pick your own subjects to learn about?
2. What if you could learn any subject just by touching a textbook?
3. What if you were suddenly invisible whenever you stepped inside of school grounds?
4. What if you had $100,000 to make any one improvement to your school?
5. What if you could pick a field trip to anywhere in the world?
6. What if you could choose to be excellent at one sport?
7. What if you could learn any one subject from an expert, living or dead?
8. What if you could choose one subject to never have to study again?
9. What if you could interview famous figures from history?
10. What if school was like “The Magic School Bus” and you could take extraordinary field trips?
11. What if you could hire one famous person to be a teacher?
12. What if you couldn’t study your first choice college major?
13. What if you could choose your own superlative in the yearbook?
14. What if you could pick the new school mascot?
15. What if you could choose one animal to keep as a classroom pet?
16. What if you could choose any chef or restaurant to cater school lunch for a day?
17. What if you could change any one thing about school?
18. What if you could teach a class?
19. What if you could choose any one historical period to live in?
20. What if you could choose any one book to live in?
21. What if you could design your own science experiment?
22. What if you saw a fellow student being bullied?
23. What if you found out your teacher was secretly an alien?

Conclusion

What if questions can be a fun way to spark imagination and creativity, improve critical thinking skills, break down barriers, and help folks get to know each other better. The what if game is an amusing way to pass time and can be an effective team building tool. You can ask as many or as few questions as you like, and can ask follow-up questions to get responders to explain their reasoning.

Next, check out this collection of conversation starters and this list of this or that questions.