Ryan | Sep 4, 2019 | 0
99 Really Interesting Questions – Spark fun, unexpected conversations.
One of the easiest ways to appear interesting (and to actually be interesting) is to ask interesting questions.
When you have interesting questions to ask people, you show not only that you think interesting thoughts, but you are also engaged in what others are thinking about.
That’s why it’s all about having the right questions to ask. If you have interesting questions to ask someone, you also get them interested in you and what you have to say.
Here are all the interesting questions you’ll need for all your upcoming conversations.
If you don’t have time to browse and just need a few of the best interesting questions right away, take any of these and enjoy the results instantly.
Here are the 12 best interesting questions:
1. Would you rather be in a real-life version of The Walking Dead or a real-life version of Game of Thrones?
Choose your awful, hopeless landscape to try to survive in!
2. Would you rather have Batman’s skills, money, equipment, and lifestyle or end crime around the world for good but be poor and unnoticed?
A fun way to discuss the reasons we do good things.
3. How long would you last in a zombie apocalypse?
Everyone likes to think of themselves as a survivor, but this requires a serious look at your prospects.
4. What “old person” things do you do?
Bond over your enjoyment of puzzles and eating dinner in the middle of the afternoon.
5. What did you think was cool then, when you were young but isn’t cool now?
The opposite of the interesting question above: discuss your youthful embarrassments.
6. If you could know the absolute and total truth to one question, what question would you ask?
Find out what question really plagues people.
7. What is the most unprofessional thing you’ve seen someone do?
A great interesting question to ask to colleagues.
8. You are about to get into a fight, what song comes on as your soundtrack?
Discover everyone’s pump-me-up song.
9. What is something that most people learn only after it’s too late?
A little more philosophical, and a great way to start sharing life experience.
10. What is the best way the 1% could spend their money?
This interesting question allows you to get just a little political without offending anyone.
11. How many friends do you have on Facebook and how many actually mean something to you?
Discuss lost friends and what friendship means in the Facebook-era.
12. If you could ask advice from any historical figure, who would it be? What would you ask them?
Do they need Napoleon’s help on business takeovers or Picasso to help find inspiration?
Getting beyond just interesting questions, if you want a great conversation, you need interesting conversation topics. Those conversation topics have to hold people enough to build a conversation that gets beyond trivialities.
Use some of these questions to start discussions that keep everyone interested.
Here are 12 interesting conversation topics:
13. Which of your personality traits has been the most useful?
It’s not the best trait, it’s the most useful, which makes people think a little harder.
14. How important are strong family ties to you?
Whether close or not, family informs how all of us view the world.
15. If you had a theme song, what would it be?
Silly, and yet this interesting question can tell you a lot depending on the song choice.
16. If Mars was livable, would you accept a one-way ticket there?
It would take guts, a sense of adventure, and maybe a reason to run away, all great to explore in conversation.
17. What’s a movie you can practically quote from start to finish?
Discuss taste in film and quote along if you know the same movie.
18. If you could write one new law that everyone had to obey, what law would you create?
Play emperor for a day and write a just or silly law. Then explore the consequences.
19. What do you like more, being a leader or a follower?
If you get honest answers, this leads to a very interesting conversation.
20. What’s one pet peeve of yours that you wish that you could get rid of–because it hampers your enjoyment of life?
Germophobia? Grammar nazi? What issue is more a burden than fun?
21. The house is on fire, but everyone is safely out, the pets are safely out, and all wallets/cash are saved. If you could make one last dash to get something, what would it be?
Another way of asking what the most precious object is for someone.
22. When you have 30 minutes of free-time, how do you pass the time?
What we do with our free time says a lot about us.
23. What do you miss most about being a kid?
We all feel some nostalgia for our lost innocence.
24. What, if anything, have you ever re-gifted?
Find out what not to buy someone and also why they didn’t want something.
To get into a decent conversation, you have to start one first. Having some interesting questions for conversation starters really helps set the tone, so your conversation partners know where you want this talk to go.
Use some of the questions below to start some great chats.
Here are 11 interesting conversation starters:
25. You’re a mad scientist, what scientific experiment would you run if money and ethics weren’t an issue?
Play mad scientist and get some great creative answers.
26. If you were given one thousand acres of land, what would you do with it?
Farm it? Sell it off? Build a castle? The answers are endless.
27. If you could hack into any one computer, whose computer would you choose?
Would it be a president’s or dictator’s? Or an ex-partner’s?
28. What’s the most interesting thing you’ve read or seen this week?
Sometimes this easy prompt leads to the most interesting conversations.
29. If you could change 3 things about your country, what would you change?
Keep it to three and see what issues really interest people.
30. Who is the most impressive famous person alive today? Why?
The choice says a lot about what the person cares about.
31. How do you feel about cars becoming fully autonomous and having no steering wheel, breaks, or accelerators?
Sit back and enjoy the ride or fear for the robots taking over?
32. What fact amazes you every time you think of it?
You’ll get a lot of crazy facts with this one.
33. What gets too much attention in the news?
Find out and then find out what needs to get more attention.
34. If you had to flee the country, where would you choose to live?
Would you exile yourself in Paris or on a beach in the Caribbean?
35. Do you think psychic abilities exist? Which one would you like to have?
People have surprisingly strong feelings on this issue on both sides.
Use these interesting questions to take any relationship of any sort to the next level.
Here are 10 interesting get to know you questions:
36. What is the silliest thing you have heard people say about you?
Start off with some light embarrassment and a good laugh to open things up.
37. Do you have any ridiculous goals in life?
Everyone dreams big, most people are just too shy to share it.
38. What’s the most spontaneous thing you’ve ever done?
A big trip somewhere? Getting married? Or saying yes to that job that terrified them?
39. What cartoon do you still like to watch?
A guilty-pleasure from childhood, but one that will say a lot about the person.
40. What was your favorite fairy tale growing up?
Another one from childhood that opens up a lot of interesting characteristics.
41. What skill or craft would you like to master?
Fishing? Knitting? Or is it something wilder?
42. How did you find out that Santa isn’t real?
Everyone has a story behind that little trauma.
43. What personality trait do you wish you had?
Seeing what they think they lack says a lot about how they see themselves overall.
44. What is the most hilarious childhood memory you can think of?
A lighter side to the past, and one that will bring a smile to their face while you learn their history.
45. What’s the meanest thing you’ve ever done to someone to get back at them?
We’ve all given into revenge on some level, get that personal story out of them.
Asking the right question might just be the best way to really get to know her, so try these interesting ones next time.
Here are 11 interesting questions to ask a girl:
46. If you were arrested with no explanation, what would your friends and family assume you had done?
Find out what outrageous quality she’s most known for.
47. In 40 years what do you think you’ll be most nostalgic about?
Try to look at the present from the future and see what she really loves about today.
48. Would you rather go to a club, house party, or a small get together of 4 or 5 friends?
A great way to find out how she likes to party.
49. Are any of your friends completely opposite to you or are most of them similar to you?
You’re asking what she likes in people: similarity or contrast.
50. Using one word, how would you describe your family?
Everyone has strong feelings about family, this opens that door with a single word.
51. What 3 famous people, living or dead, would you want at your fantasy dinner party?
This interesting question tells you all about who and what she admires.
52. If you could shop for free at one store, which one would you choose?
Get the inside scoop on where to buy her gifts.
53. What movie can you watch over and over again?
Find out and then suggest you watch it together.
54. Which pet made the most impact in your life?
Get the story of the pet, and you’ll get an important part of her story too.
55. When have you felt your biggest adrenaline rush?
Extreme sports, video games, or scary movies: what really gets her blood pumping?
56. If you had to bury treasure where would you hide it?
This question is fun and creative, likely catching her a little off-guard.
Getting close to another guy can be as tricky as it is with girls. Finding interesting questions to ask a guy that not only get him talking but get him interested in sharing is key.
Use these interesting questions for your next conversation with a guy you want to know better.
Here are 11 interesting questions to ask a guy:
57. Superman or Batman?
The age old question, and sure to start a debate if this guy knows his comics.
58. 100 duck sized horses or 1 horse sized duck?
Give him a chance to show off his duck and horse strategy skills.
59. If you were given a one-minute ad slot during the Super Bowl that you couldn’t sell, what would you fill it with?
Probably with ducks and horses.
60. What is the most important object you own?
His phone? His clothes? Or is it something more personal? Whatever his answer, it’ll tell you the kind of person he is.
61. What event in your life would make a good movie?
With this interesting question, you can trick him into telling his story.
62. On a day held in your honor, what would people have to do?
Have fun imagining all the elaborate celebrations of the one and only you.
63. What food combination do you want to ban?
Everyone has a food pet peeve. Let him vent about his.
64. What’s your first executive order as king of (this coffee shop, this grocery store, this room)?
Hopefully free coffee, but let him have his say first.
65. If you could be great at one sport which would you choose?
Most guys have dreamed of being a pro athlete in something, find out his missed shot.
66. If you could dedicate your life to solving one problem, what problem would you choose?
It’s open to either an amusing or genuine response. Up to him.
67. If you had one day left to live on the Earth, what would you do?
A silly question that can lead to some very insightful answers.
Keeping the conversation going when you’re in a relationship can be even more tricky than starting a good conversation with a stranger. After all, all the best topics have already been covered.
To keep the conversation interesting, you need interesting questions for couples. Use some of these to add a spark to your discussions with your partner.
Here are 11 interesting questions for couples:
68. What makes a person beautiful to you?
This sets up a simple discussion of physical beauty, or open to something much deeper.
69. What’s a big favor you have done for a friend? How about a big favor that a friend has done for you?
You may think you know all your partner’s stories, but this could open new ones.
70. If you turn into your partner for a day, what would you do?
A great way to find out what your partner thinks your life is like.
71. If we had only one weekend together before the end of the world and we were to spend it together, what do you think we’d do?
Discover what activities your partner really cherishes doing with you.
72. What class would you love to take together?
A couple that keeps exploring new things finds new ways to stay together.
73. What makes you feel young?
Keeping that youthful energy is crucial to keeping a relationship strong.
74. What do you do when you’re angry? How can I help?
Having this conversation on a calm day is a great way to avoid major argument mistakes in the future.
75. What Would Be Your “Perfect” Day?
Keep that information close so you can use it someday to give your partner all they want.
76. Out of all the world’s languages, which one sounds funniest to you?
A great opportunity to have a little fun impersonating languages and making each other laugh.
77. What’s the title of your quarter-life biography?
See how they view their life so far and what they hope is coming up.
78. Where is your favorite place to be with me?
Sometimes just the name of a place is enough to start a long conversation of all the great times you’ve had together.
Sometimes, interesting isn’t enough for a question. You need your interesting questions to also be funny questions to ask. Getting people laughing lets them open up more and answer your interesting question more honestly.
Try these out next time to add fun as well as great topics to your conversation.
Here are 10 interesting and funny questions to ask:
79. Would you rather… Talk like Yoda or breathe like Darth Vader?
Try out both for a while and see which one gets the best laughs.
80. What would be the absolute worst name you could give your child?
Try a few out and see if any stick as nicknames.
81. What mildly annoying curse do you wish you could curse people with?
Bad breath? Permanent bad hair? Or an inability to read social cues? Find your best annoying curse.
82. What’s the weirdest thing you did as a child?
Get into old childhood habits and expand to childhood memories.
83. How would you conquer the earth?
Everyone has developed a plan at some point. Time to share.
84. Why can’t most people keep up with trends in music / fashion / tech as they get older?
A great one to discuss if you’ve just passed the dreaded line from young adult to proper adult.
85. If you could swim in any liquid what would it be and why?
A strange question and yet one, when people think about it, likely to lead to some interesting answers. Jell-O anyone?
86. What is the worst pet you have ever had?
People love to talk about the good pets. Make them tell you about the ones they never bring up.
87. If you could ask your pet 3 questions, what would they be?
Silly and yet, who isn’t curious about the world of animals?
88. What Simpsons character are you?
Share some great Simpsons moments and find out more about your conversation partners.
An interesting question can be more than just a way to fill the time. It can also lead to some really deep places.
By having deep questions to ask that are also interesting questions, you are more likely to lead the conversation where you want it to go. Try some of these out next time you want to get a little deeper in your chatting.
Here are 11 interesting but deep questions to ask:
89. What separates true friends from acquaintances?
We all instinctively feel the line, but now try to define it.
90. Is gift giving common among all human cultures?
If it is, what does that say about us as a species?
91. If you could do so, how would you change the world?
It’s a lot of hypothetical responsibility, how would you use it? What would the consequences be?
92. If you were immortal for a day, what would you do?
Another way of asking if the fear of death is holding you back.
93. Would you break the law to save a loved one?
Get the answer, then dig into which laws you would actually break.
94. Where do you find meaning in your life?
We all need meaning, how do those around you find it? And is it enough for them?
95. What percentage of your life do you feel truly alive?
Can you raise that percent higher?
96. What has taken up too much of your life?
What are people wasting their lives on?
97. What job do you think you were born to do?
Another way of asking what someone thinks their purpose is.
98. Do you believe things happen for a reason?
One of the most central questions of all time.
99. If you could replace war with something to settle countries’ differences, what would it be?
Find the recipe for world peace at your table.
Downloadable List of Interesting Questions
Here is a downloadable list of interesting questions (right click the image and select Save Image As…):
More Best Questions to Ask
If you are looking for even more interesting questions to build up your conversation skills, Mantelligence has all you could possibly need. Try these:
- When you want to get out of a conversation rut, try these random questions
- Get some crazy answers from unexpected questions with our weird questions to ask
- Want to give a great impress to new people? Use some funny get to know you questions
One of the great things about asking interesting questions is how easy it is. Just follow these three steps:
1. Ask an interesting question that fits the audience
Make sure your audience is the sort that will like these types of questions, and then tailor those questions to the audience. Don’t go too silly or bawdy with the boss, but don’t go to conservative with your friends.
2. Ask an interesting question that fits the situation
Even if people like interesting questions, make sure you pick the right situation for it. Letting loose with colleagues after work is a great time, while it might be better to hold off right before a board meeting.
3. Ask an interesting question that fits the present conversation
Unless you’re looking to go complete non sequitur, choose a question that slides easily into the conversation. Use conversation starters early, and then use others when the conversation is drifting in that direction.
When you are struggling to come up with questions to ask someone, it’s probably because you want those questions to be interesting.
Thankfully, now you’ve got tons of interesting questions to ask people in every situation, so that you never have to have another bland conversation if you don’t want to.
With these interesting questions to ask someone, you’ll now be able to generate enjoyable conversations that build relationships and just pass the time a lot more pleasurably.