350 Good questions to ask

Try to be creative as you can and have fun with the questions. And don’t forget to ask some follow up questions!

Good questions to ask

Here’s our insanely long list of great questions to ask. If you’re looking for a more organized list, head over to 250+ Quality Conversation Starters & Questions

Good questions to ask (Part 1)

1. Which protagonist from a book or movie would make the worst roommate?
2. What outdoor activity haven’t you tried, but would like to?
3. What do a lot of people have strong opinions about, even though they know very little about it?
4. What fictional characters have you had a crush on over the years?
5. What do a lot of people hope will happen, but it’s just not going to happen?
6. What’s your best example of easy come, easy go?
7. What happens in your country regularly that people in most countries would find strange or bizarre?
8. Do you think that children born today will have better or worse lives than their parents?
9. Which apocalyptic dystopia do you think is most likely?
10. When was the last time you were hopelessly lost?
    

    
11. If there was a book of commandments for the modern world, what would some of the rules be?
12. What’s the weirdest thing about modern life that people just accept as normal?
13. What’s the grossest food that you just can’t get enough of?
14. What’s the most amazing place in nature you’ve been to?
15. What weird potato chip flavor that doesn’t exist would you like to try?
16. What’s the cutest thing you can imagine? Something so cute, it’s almost painful.
17. What languages do you wish you could speak?
18. What’s the most embarrassing story from your childhood?
19. What problem are you currently grappling with?
20. What’s the most ridiculous animal on the planet?
21. What bit of trivia do you know that is very interesting but also very useless?
22. If your job gave you a surprise three day paid break to rest and recuperate, what would you do with those three days?
23. What mythical creature do you wish actually existed?
24. What animal would be cutest if scaled down to the size of a cat?
25. What does the opposite sex do that you wish that you could do, but it’s not anatomically feasible, or it’s socially frowned upon?
26. What’s the weirdest crush you’ve had?

Good questions to ask (Part 2)

1. What kinds of things do you like to cook or are good at cooking?
2. If you could switch two movie characters, what switch would lead to the most inappropriate movies?
3. What’s the funniest thing you’ve done while your mind was wandering?
4. What outdated slang do you use regularly?
5. What are some brilliant examples of misdirection you’ve seen?
6. What two films would you like to combine into one?
7. What’s the most relaxed animal you’ve seen in the wild?
8. What would be the best thing you could reasonably expect to find in a cave?
9. What’s quickly becoming obsolete?
10. What’s the most boring sport, and what would you do to make it more exciting?
11. What country is the strangest?
12. What seemingly innocent question makes you think, “It’s a trap!”?
13. What escalated very quickly?
14. What values are most important to you?
15. What’s your grossest bug story?
16. If you lived in a virtual reality world of your creation, what would it look like?
17. What awful movie do you love?
18. What movie or book do you know the most quotes from?
19. What was the most important appointment or deadline you missed?
20. What was the most impressive physical feat you’ve managed to pull off?
21. What’s the scariest non-horror movie?
22. If you could talk to animals and they would understand you, but you couldn’t understand them, what would you do with that power?
23. What are some misconceptions about your hobby?
24. Which celebrity is the most likely to have a collection of canes that are just for show?
25. What’s your best story from a wedding?

Good questions to ask (Part 3)

1. What do you think you are much better at than you actually are?
2. Who do you feel like you know even though you’ve never met the person in real life?
3. What was the last situation where some weird stuff went down, and everyone acted like it was normal, and you weren’t sure if you were crazy or everyone around you was crazy?
4. What profession doesn’t get enough credit or respect?
5. What’s the best lesson you’ve learned from a work of fiction?
6. What’s the clumsiest thing you’ve done?
7. What’s your best example of fake it till you make it?
8. What movie, picture, or video always makes you laugh no matter how often you watch it?
9. What scientific discovery would change the course of humanity overnight if it was discovered?
10. What’s the weirdest conversation you’ve eavesdropped on?
11. Who did you use to look up to, but they screwed up, and you lost faith in them?
12. What’s the most annoying thing about the social media platform you use most often?
13. What would be the worst food to be liquefied and drunk through a straw?
14. Do you like things to be carefully planned, or do you prefer to just go with the flow?
15. What animal is the most majestic?
16. What’s something that everyone agrees we should change, but somehow it never changes?
17. What near future predictions do you have?
18. What big event do you think will happen soon that most people aren’t expecting?
19. What’s the hardest you’ve ever worked?
20. If you were a clown-themed superhero, what powers would you have?
21. Do you think that aliens exist?

Good questions to ask (Part 4)

1. How much do you plan/prepare for the future?
2. What’s the worst backhanded compliment you could give someone?
3. What’s the most epic way you’ve seen someone quit or be fired?
4. What’s about to get much better?
5. What’s the funniest pickup line you’ve heard?
6. What’s the dumbest thing someone has argued with you about?
7. What animal or plant do you think should be renamed?
8. If magic was real, what spell would you try to learn first?
9. What horror story do you have from a job you’ve had?
10. In the past people were buried with the items they would need in the afterlife, what would you want to be buried with you so you could use it in the afterlife?
11. Who is the most creative person you know?
12. What’s the funniest actual name you’ve heard of someone having?
13. What riddles do you know?
14. What’s your secret talent?
15. How much do you think names affect the outcomes of people’s lives?
16. What would be an accurate tag line for each month?
17. What naps are the most satisfying?
18. How would your country change if everyone, regardless of age, could vote?
19. What’s the best sandwich you’ve ever had?
20. What inconsequential superpower would you like to have?
21. Who in your life is the worst at using technology?
22. What’s your favorite holiday movie?
23. When was the last time you face palmed?

Good questions to ask (Part 5)

1. What has been blown way out of proportion?
2. What was cool when you were young, but isn’t cool now?
3. What’s the most beautiful beach you’ve been to?
4. When’s censorship warranted?
5. What social stigma does society need to get over?
6. What’s the weirdest text or email you’ve gotten?
7. What are some of the dumbest lyrics you’ve heard in a song?
8. When was the last time you were snooping and found something you wish you hadn’t?
9. What product do you wish a company would make a “smart” version of?
10. What was the most unsettling film you’ve seen?
11. If people receive a purple heart for bravery, what would other color hearts represent?
12. If someone narrated your life, who would you want to be the narrator?
13. What’s the most overrated product out on the market?
14. What’s something that all your friends agree on?
15. What’s something people don’t worry about but really should?
16. What goal do you think humanity is not focused enough on achieving?
17. What weird food combinations do you really enjoy?
18. What do you think could be done to improve the media?
19. What’s the most elongated rabbit hole you’ve been down?
20. Would you want the ability to hear the thoughts of people near you if you couldn’t turn the ability off?
21. What word do you always mispronounce?
22. What outfit could you put together from clothes you own to get the most laughs?
23. What’s something common from your childhood that will seem strange to future generations?
24. What’s the most annoying animal you’ve encountered?
25. What character in a movie could have been great, but the actor they cast didn’t fit the role?
26. What artist or band do you always recommend when someone asks for a music recommendation?
27. How do you judge a person?

Good questions to ask (Part 6)

1. What food is delicious but a pain to eat?
2. What’s the most incredible true story you’ve heard?
3. What food have you never eaten but would really like to try?
4. What story you’ve heard has stayed with you and always disturbs you every time you think about it?
5. If cartoon physics suddenly replaced real physics, what are some things you would want to try?
6. What’s the weirdest thing you’ve found lying on the ground/side of the road?
7. What would be the most disturbing thing to keep occasionally finding around your house?
8. Where are some unusual places you’ve been to?
9. What’s the best / worst practical joke that you’ve played on someone or that was played on you?
10. What topic could you spend hours talking about?
11. How do you make yourself sleep when you can’t seem to get to sleep?
12. Which celebrity do you think is the most down to earth?
13. What’s the oldest thing you own?
14. What do you do to make the world a better place?
15. What’s the craziest video you’ve ever seen?
16. What company do you despise?
17. What game have you spent the most hours playing?
18. What’s the most depressing meal you’ve eaten?
19. What’s your “and then it got worse” story?
20. What’s the worst thing you ate from a fast-food restaurant?
21. What’s the worst movie trope?

Good questions to ask (Part 7)

1. What elements of pop culture will be forever tied in your mind to your childhood?
2. What has someone borrowed but never given back?
3. Do you eat food that’s past its expiration date if it still smells and looks fine?
4. What nicknames do you have for people in your life?
5. What odd smell do you really enjoy?
6. What was the last photo you took?
7. What are your most important rules when going on a date?
8. In what situations do you wish you could throw down a smoke bomb and disappear?
9. What’s the worst hairstyle you’ve ever had?
10. What are you interested in that most people aren’t?
11. When you are old, what do you think children will ask you to tell stories about?
12. What was the worst shopping experience you’ve ever had?
13. What do you think you do better than 90% of people?
14. What word do you always misspell?
15. What’s the most historic thing that has happened in your lifetime?
16. What’s something that will always be in fashion, no matter how much time passes?
17. When was the last time you slept for more than nine hours?
18. What’s the most interesting building you’ve ever seen or been in?
19. What’s your go-to casino game?
20. What’s the best way you or someone you know has gotten out of a ticket/trouble with the law?
21. What was the darkest movie you’ve ever seen?
22. If you had a giraffe that you needed to hide, where would you hide it?
23. What’s the silliest thing you’ve convinced someone of?
24. What did you like/dislike about where you grew up?

Good questions to ask (Part 8)

1. What’s incredibly cheap, and you would pay way more for?
2. What movie can you watch over and over without ever getting tired of?
3. What’s the biggest overreaction you’ve ever seen?
4. What’s the funniest joke you know by heart?
5. Where are you not welcome anymore?
6. What “old person” things do you do?
7. What small change significantly improves a person’s appearance?
8. What’s your haunted house story?
9. What’s a common experience for many people that you’ve never experienced?
10. What’s the silliest thing you’ve seen someone get upset about?
11. If you built a themed hotel, what would the theme be, and what would the rooms look like?
12. What food do you crave most often?
13. What’s the saddest scene in a movie or TV series?
14. What’s the most ridiculous thing you have bought?
15. What are you currently worried about?
16. Where’s your go-to restaurant for excellent food?
17. What’s something commonly done that gets progressively weirder the more you think about it?
18. What’s the most creative use of emojis you’ve ever seen?
19. What’s the spiciest thing you’ve ever eaten?
20. What about the opposite sex confuses you the most?
21. What’s your best story of you or someone else trying to be sneaky and failing miserably?
22. What’s your good luck charm?
23. What’s the most anxiety-inducing thing you do regularly?
24. What’s your funniest story involving a car?
25. What’s the funniest thing you’ve seen a kid do?
26. Do you think that humans will ever be able to live together in harmony?
27. What’s the shadiest thing you’ve seen someone do?
28. What really needs to be modernized?

Good questions to ask (Part 9)

1. If you were given unlimited resources, how would you lure the worst of humanity into one stadium at the same time?
2. What actors or actresses can’t play a different character because they played their most famous character too well?
3. As a child, what did you think would be awesome about being an adult, but isn’t as awesome as you thought it would be?
4. What’s the most interesting documentary you’ve ever watched?
5. When was a time you acted nonchalant but were going crazy inside?
6. What from the present will withstand the test of time?
7. What songs do you feel compelled to sing along with when you hear them, even if you don’t totally know all the words?
8. Where’s the line between soup and cereal?
9. What’s the smartest thing you’ve seen an animal do?
10. What invention doesn’t get a lot of love, but has dramatically improved the world?
11. What do you need help with most often?
12. What was the last song you sang along to?
13. Have you ever been addicted to a game?
14. What still makes you cringe when you think back on it?
15. What skills are rarely taught but extremely useful?
16. Who do you go out of your way to be nice to?
17. What do you think about when you hear the word “classy”?
18. What are some of the most common misconceptions?
19. What sport could you play the longest in a televised game, without anyone discovering you aren’t a professional athlete?
20. What do you hate most and love most about your car?
21. What’s wrong but sounds right?
22. What’s better broken than whole?

Good questions to ask (Part 10)

1. What is the most amazing slow motion video you’ve seen?
2. What’s something that everyone knows is true, but we don’t like to admit it?
3. What’s something that I don’t know?
4. If money and practicality weren’t a problem, what would be the most exciting way to get around town?
5. Think of a brand, now what would an honest slogan for that brand be?
6. What songs hit you with a wave of nostalgia every time you hear them?
7. Who do you wish you could get back into contact with?
8. What’s the most rage-inducing game you’ve ever played?
9. What word is a lot of fun to say?
10. What actors or actresses play the same character in almost every movie or show they do?
11. What did you believe for way too long as a child?
12. What memory of yours feels real but is most likely false?
13. If you could hack into any one computer, which computer would you choose?
14. What piece of “art” would you create if you had to pretend to be an artist and submit something to a gallery?
15. What product or service is way more expensive than it needs to be?
16. Who was your craziest / most interesting teacher
17. If you were moving to another country, but could only pack one carry-on sized bag, what would you pack?
18. If you had a HUD that showed three stats about any person you looked at, what three stats would you want it to show?
19. What movie universe would be the worst to live out your life in?
20. What’s the best and worst thing about the country you are from?
21. What would be some of the downsides of certain superpowers?
22. Where do you get most of the decorations for your home?
23. Who in your life has the best / worst luck?
24. What’s the funniest TV show you’ve ever seen?
25. Where is the best place you’ve been for taking walks?

Good questions to ask (Part 11)

1. What habit do you have now that you wish you started much earlier?
2. What would the box with all your hopes and dreams inside look like?
3. What were you entirely sure of until you found out you were wrong?
4. What’s the most comfortable bed or chair you’ve ever been in?
5. What job doesn’t exist now but will exist in the future?
6. What app can you not believe someone hasn’t made yet?
7. What’s some insider knowledge that only people in your line of work have?
8. What’s the most awkward thing that happens to you regularly?
9. What’s the opposite of a koala?
10. What’s the most expensive thing you’ve broken?
11. If you owned a restaurant, what kind of food would it serve?
12. What did you Google last?
13. When was the last time you felt you had a new lease on life?
14. What do you do when you hear something fall in the middle of the night while you are in bed?
15. What would your perfect bar look like?
16. An epic feast is held in your honor, what’s on the table?
17. What’s the most boring superhero you can come up with?
18. What happens regularly that would horrify a person from 100 years ago?
19. What would a world populate by clones of you be like?
20. What tips or tricks have you picked up from your job/jobs?
21. What makes you roll your eyes every time you hear it?
22. Tear gas makes people cry, and laughing gas makes people giggle, what other kinds of gases do you wish existed?
23. If you were in charge of renaming things so that their names would be more accurate, what terms would you come up with?
24. What was one of the most interesting concerts you’ve been to?
25. What’s the most physically painful thing you’ve ever experienced?
26. What’s the most ironic thing you’ve seen happen?
27. What’s your “Back in my day, we…”?

Good questions to ask (Part 12)

1. What would the adult version of an ice-cream truck sell, and what song would it play?
2. When did something start out badly for you, but in the end, it was great?
3. What’s your best example of correlation not equaling causation?
4. What are some red flags to watch out for in daily life?
5. Where is the most uncomfortable place you have ever slept?
6. What’s the most frustrating product you own?
7. What brand are you most loyal to?
8. Which charity or charitable cause is most deserving of money?
9. What questions would you like to ask a time traveler from 200 years in the future?
10. What current trend makes no sense to you?
11. What was ruined because it became popular?
12. What just around the corner tech are you eager to get your hands on?
13. If animals could talk, which animal would be the most annoying?
14. What’s something that people think makes them look cool, but actually has the opposite effect?
15. When was the most inappropriate time you busted out in laughter?
16. What’s legal now, but probably won’t be in 25 years?
17. What’s the coldest you’ve ever been?
18. What’s something you really resent paying for?
19. What TV show character would it be the most fun to change places with for a week?
20. What animal would you most like to eat?
21. What naturally delicious food gets ruined when you wrap it in a tortilla?
22. When was the last time you immediately regretted something you said?
23. What’s the weirdest thing that has happened to you while working at your job?
24. What’s fine in small numbers but terrifying in large numbers?

Good questions to ask (Part 13)

1. If you could airdrop anything you want, worth two million dollars or less, anywhere you want, what would you airdrop, and where would you airdrop it?
2. If you could know the truth behind every conspiracy, but you would instantly die if you hinted that you knew the truth, would you want to know?
3. What’s something that everyone, absolutely everyone, in the entire world, can agree on?
4. Which way should toilet paper hang, over or under?
5. When was the last time you stayed up through the entire night?
6. What’s the funniest word in the English language?
7. If you were a ghost and could possess people, what would you make them do?
8. If you were given five million dollars to open a small museum, what kind of museum would you create?
9. If you wanted to slowly drive a roommate insane using only notes, what kind of messages would you leave around the house?
10. What was the best thing that happened to you today?
11. What’s the worst thing you’ve eaten out of politeness?
12. What are some of the best vacations you’ve had?
13. Which celebrity or band has the worst fan base?
14. How much of your body would you cybernetically enhance if you could?
15. What animal would be the most terrifying if it could speak?
16. What’s the most pleasant sounding accent?
17. What did you eat so much of that now you hate it?
18. What’s your worst example of procrastination?
19. If you were given one thousand acres of land that you didn’t need to pay taxes on but couldn’t sell, what would you do with it?
20. If you could have an all-expenses-paid trip to see any famous world monument, which monument would you choose?
21. What current trend do you hope will go on for a long time?
22. What’s the most annoying noise?
23. What qualities do all your friends have in common?
24. Which of your vices or bad habits would be the hardest to give up?
25. What two things are terrible when separate but great when you put them together?
26. What did you think was going to be amazing but turned out to be horrible?
27. What’s the most disgusting sounding word in the English language?
28. When was the last time you yelled at someone?
29. If you were given a Ph.D. degree but had no more knowledge of the subject of the degree besides what you have now, what degree would you want to be given to you?
30. What always cheers you up when you think about it?
31. Where do you get your news?

Good questions to ask (Part 14)

1. What was the biggest realization you had about yourself?
2. What was your most recent lie?
3. What smartphone feature would you actually be excited for a company to implement?
4. If you couldn’t be convicted of any one type of crime, what criminal charge would you like to be immune to?
5. How ambitious are you?
6. What unethical experiment would have the biggest positive impact on society as a whole?
7. Should kidneys be able to be bought and sold?
8. If you had to disappear and start a whole new life, what would you want your new life to look like?
9. What songs do you only know the chorus to?
10. Who is the most manipulative person you’ve ever met?
11. When was the last time you got to tell someone, “I told you so.”?
12. How comfortable are you speaking in front of large groups of people?
13. If you were hired to show tourists what life is really like where you live, what would you show them / have them do?
14. What fashion trend makes you cringe or laugh every time you see it?
15. What’s the craziest conversation you’ve overheard?
16. What’s the creepiest tech out there?
17. What’s the most recent show you’ve binge-watched?
18. What movie quotes do you use regularly?
19. What would be the click-bait titles of some popular movies?
20. What trend are you tired of?
21. What’s the funniest comedy skit you’ve seen?
22. Who has zero filters between their brain and mouth?
23. What inanimate object would be the most annoying if it played loud, upbeat music while being used?
24. What obstacles would be included in the world’s most amazing obstacle course?
25. What would be the worst thing to hear as you are going under anesthesia before heart surgery?
26. What’s your cure for hiccups?