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65 Interesting Questions - The Best Ones To Get To Know Them Deeper.

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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by | June 17th, 2021


If you're looking for interesting questions, don't look any further.

Mantelligence and cool questions to ask go hand in hand. One of the ways to appear interesting is by having interesting things to ask. And it's our job to make you that interesting person with the right questions.

Here are all the interesting questions you'll need for all your upcoming conversations. Let's start.

Contents

5 Best Interesting Questions

If you don't have time to browse and just need a few of the best questions as a conversation starter right away, take any of these and enjoy the results instantly.

Here are the 5 best interesting questions:

1. What “old person” things do you do?

This one isn't exactly an ice breaker question, but it's questions like this that start meaningful connections-bond over your enjoyment of puzzles and eating dinner in the middle of the afternoon.

2. What did you think was cool then, when you were young but isn’t cool now?

The opposite of the stated inquiry above: discuss your youthful embarrassments.

3. What is something that most people learn only after it’s too late?

You can go ahead and skip the small talk altogether with this deep question-a little more philosophical and also a great way to start sharing experiences.

4. What is the best way the 1% could spend their money?

This one allows you to get just a bit political without offending anyone. We can all give an interesting answer to this one because we all have ideas about money.

5. What secret do you have that no one else knows except your sibling/s?

This one is easily one of the fun questions in the mix. What's the craziest thing for someone that they never even let anyone know except their siblings? It must be a huge secret.

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5 Conversation Topics That Are Interesting

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 discussion that gets beyond trivialities.

Use some of these questions to start discussions that keep everyone interested.

Here are 5 interesting topics:

6. What’s a movie you can practically quote from start to finish?

It's the battle of someone's favorite movie. Discuss taste in film and quote along if you know the same film. It's bound to be a meaningful conversation if you dig deeper.

7. 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?

This one is fun because all important things are out of the scenario. What is a person's most favorite thing that they'd dash in a fire to retrieve? Is it something that connects to their favorite memory? Or something nonsense?

8. When was the last time you did something and regret doing it?

This one is a good question to get an idea of the personality of the other individual. It's one of those personal questions that give us a deeper look at a person

9. What guilty pleasure makes you feel alive?

This one is a great question to get to know another individual. There's something about guilty pleasures that just makes us alive. It's exciting.

10. What is that one thing that you enjoyed doing but hated by everyone else?

And this needs a follow-up. Why? What is it about that thing that they just can't seem to enjoy?

6 Interesting Conversation Starters

To get into a decent discussion, you have to start one first. Having some fascinating conversation starters helps set the tone so your discussion partners know where you want this talk to go.

Use some of the questions below to start some great chats.

Here are 6 interesting discussion starters:

11. Who is the most impressive famous person alive today? Why?

The choice says a lot about what the individual cares about. Their answer might be the person that they look up to and aim to be. It says a lot about their motivations, too!

12. Do you think psychic abilities exist? Which one would you like to have?

People have surprisingly strong feelings on this issue on both sides. It would be interesting to think of a world where every single person has psychic abilities. Would it be more chaotic? Or do you think we could live with each other like that?

13. Do you think people need to post everything on social media?

Each to his own for this one, really. We all have differing opinions on how to use social media correctly. If you think about it, there's really no handbook that tells us the "correct" way to use and consume social media.

14. Who is your favorite cartoon character and why?

Our favorite fictional character can say so much about our personality. Sometimes, our favorite cartoon characters are those characters that are a reflection of how we see ourselves.

15. What is your least favorite holiday side dish?

This random question needs to be taken note of. Never serve that side dish when your friend is over for the holidays!

16. Give up social media or eat the same dinner for the rest of your life?

It's a hard one, especially for people that rely on social media for their job. Sure, social media can just be a bad habit, but many people gain something from it.

5 Interesting Get to Know You Questions

When you want to get beyond niceties and get to know someone, you need to get to know your questions to keep their interest and allow them to open up. So what are interesting questions to ask when you want to get to know someone? Well, they are those that are not too deep, but not too shallow also.

Use these questions to take any relationship of any sort to the next level.

Here are 5 interesting get to know you questions:

17. Do you have any ridiculous goals in life?

Everyone dreams big. Most people are just too shy to share it. This one can quickly turn into a funny question if someone's goals are that ridiculous! It won't hurt to give in a good laugh.

18. What’s the most spontaneous thing you’ve ever done?

A big trip somewhere that quickly became their favorite place? Getting married? Or being brutally honest in a job interview? Whatever it is, this open-ended question is the right time to give a salute to them!

19. What cartoon do you still like to watch?

A guilty pleasure from childhood, but one that will say a lot about the person.

20. What personality trait do you wish you had?

Seeing what they think they lack says a lot about how they see themselves overall. This one can seem innocent but, if dug deeper, can turn into a good philosophical question.

21. 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.

6 Interesting Questions to Ask a Girl

When you are thinking about questions to ask a girl, you know they can't be boring, simple questions about the weather. It would be best if you had interesting questions to ask a girl so that you stand out.

Asking the right question might just be the best way to get to know her, so try these interesting ones next time.

Here are 6 interesting questions to ask a girl:

22. 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 loves about today.

23. Using one word, how would you describe your family?

Everyone has strong feelings about family. This opens that door with a single word.

24. What 3 famous people, living or dead, would you want at your fantasy dinner party?

This one tells you all about who and what she admires. Make it even more fun by letting her give you details on what she wants to happen at this fantasy dinner party.

25. If you could shop for free at one store, which one would you choose?

Get the inside scoop on where to buy her gifts. Be boyfriend material by taking notes!

26. If I am a time traveler, will you travel back in time with me without going back to the present?

If she's your girlfriend, she probably will! This one is really good because it's a unique thought to have.

27. If it will be the last sandwich on earth, will you give it to your favorite dog or me?

Icebreaker questions like this are funny. It's great to share a laugh with a friend here and there. Hopefully, it doesn't start an argument! But if we're being honest, dogs are pretty cool. Cooler than humans.

6 Interesting Questions to Ask a Guy

Getting close to another guy can be as tricky as it is with girls. Finding interesting questions to ask a guy that not only gets him talking but gets him interested in sharing is vital.

Use these questions for your next conversation with a guy you want to know better.

Here are 6 questions to ask a guy:

28. 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. Talking about something close and dear to us is a lot of people's favorite subject.

29. What event in your life would make a good movie?

With this one, you can trick him into telling his story.

30. What food combination do you want to ban?

Everyone has a food pet peeve. Let your friend vent about his. Maybe he has tried something with his favorite ice cream flavor that scarred him for life.

31. 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 your friend. Whatever the answer would be, it just means there's one thing that people want to change in our world. No matter how small.

32. Which among your biggest fear are you willing to overcome?

We all have fears. That doesn't mean we're all cowards. It's about what we're doing to overcome them that says how courageous we are. Whatever his answer is, immense respect for him!

33. What does your perfect day look like?

He must fill it with his favorite place, favorite color, favorite movie, and so on. An ideal day would feel like something out of a movie. This one is a good one to ask him to know what makes him happy.

6 Questions for Couples

Keeping the discussion going when you're in a relationship can be even more tricky than starting a good discussion with a stranger. After all, you may have covered all the best topics out there.

To keep the discussion interesting, you need exciting questions for couples. Use some of these to add a spark to your conversations with your partner.

Here are 6 questions for couples:

34. 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.

35. What makes you feel young?

Keeping that youthful energy is crucial to maintaining a strong relationship.

36. What do you do when you’re angry? How can I help?

Having this discussion on a calm day is a great way to avoid significant argument mistakes in the future. It's essential to take note of this so you can know what to expect.

37. What is the nicest thing that I gave you that you never expected?

You might be surprised yourself by the answer you get from them. Sometimes, it's those little things we don't give much thought to that make the most impression on them.

38. Which favorite song do I always listen to in the car?

This is the perfect thing to ask to know how much they know you.

39. What is the first date question that I asked you?

It's always good to reminisce about your first date. It can bring back all the happy memories and remind you why you're with this person after all this time.

5 Interesting and Funny Questions to ask

Sometimes, interesting isn't enough. You need your questions also to be funny questions to ask. Getting people laughing lets them open up more and answer you are interesting question more honestly.

Try these out next time to add fun as well as great topics to your discussion.

Here are 5 interesting and funny questions to ask:

40. What would be the absolute worst name you could give your child?

Try a few out and see if any stick as nicknames.

41. What’s the weirdest thing you did as a child?

Get into old childhood habits and expand to childhood memories.

42. What are things that you posted on Facebook that you regret posting?

We all had those moments. Good thing we can always delete something on Facebook when we stumble upon it and get super cringe-y vibes.

43. What would be a common reason your siblings would fight?

No matter how close siblings are, there's always a reason to fight. Sometimes, it's just playful. Sometimes, it goes deeper than that. However, sibling connections are something important.

44. What is the funniest moment ever caught in a tv show?

There are a lot of funny moments in tv shows. Some are more memorable than others.

6 Interesting but Deep Questions to ask

Questions can be more than just a way to fill the time. It can also lead to some extreme places.

By having deep questions to ask that are also interesting, you are more likely to lead the discussion where you want it to go. Try some of these out next time you want to get a little deeper into your chatting.

Here are 6 interesting but deep questions to ask:

45. 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?

46. If you were immortal for a day, what would you do?

This one is another way of asking if the fear of death is holding you back.

47. 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?

48. Is your mom your role model in life? Why?

We all look up to moms. They're the light of our lives. No matter our connection with our moms, we wouldn't be here without them.

49. How important is a sense of humor when you choose your partner?

Some people think it's an essential thing, so as for the relationship not to get boring no matter how long it has been. For others, it's just a plus point.

50. If you have the chance to meet your favorite author, will you let him write the story of your life?

They say you should never meet your idols, but in this case, would you let your heroes write your story?

5 Interesting Interview Questions

Anyone who has sat through more than a couple of interviews knows that interview questions are not just boring. They're rarely helpful. It's the same questions with the same dull answers that everyone is just trying to get through.

Throw a curveball into your next interview by asking some of these interesting interview questions. Whether you end up making the hire or not, you'll have a far better discussion while you decide.

Here are 5 interesting interview questions:

51. Have you ever loved what you were working on so hard you lost track of time?

Find out if they have that passion for this job. Sometimes, we're too into what we're doing that we don't even realize how long we've been working on something. Time flies when we're having fun.

52. Should someone be sorry for wanting to be perfect?

Let them weigh the importance of perfection versus the consequence of perfectionism. This one will tell you a lot about an individual's values when it comes to perfection.

53. How do you define a dream job?

And to what lengths would they go to achieve their dream job?

54. Do you think strong relationships are easy to maintain in a workplace?

When it comes to connections in the workplace, everyone has a different thing to say.

55. What is the worst thing that happened in your personal life that affected your focus at work?

We should always prioritize ourselves and family over our work, but what was so bad that affected one's work to a great extent?

5 interesting ice breaker questions

Where would we be without ice breaker games? We'd probably be a lot more uncomfortable, at the very least. But just because we're grateful for ice breaker questions doesn't mean all of them are winners. Some can be downright dull.

Avoid the dullness by making sure you use these exciting ice breaker questions the next time you try to get people to open up.

Here are 5 interesting ice breaker questions:

56. If the internet wasn’t invented, how different do you think we would be?

Well, to start, you wouldn't be reading this right now. What would you be doing if you weren't on the internet reading this, anyway?

57. Do you believe that we all have souls?

This one can lead to a flippant or intensely deep discussion, but it'll always be interesting. We all have opinions when it comes to anything beyond the physical things that we see and feel.

58. What superpower do you think can save the earth from being destroyed?

There are many superpowers in the world, but is there one that's strong enough to save the whole world on its own?

59. Is your dream month-long vacation includes free alcohol and all your favorite food?

I mean, whose dream vacation doesn't involve these things, right?

60. What ice cream flavor do you think should never exist?

There are so many ice cream flavors that are questionable. However, if you try them, maybe they do work as an ice cream flavor.

5 interesting Never Have I Ever Questions

When throwing around never have I ever questions; it's easy to get nervous as your turn comes around. You don't want to ask a real clunker, and that's far too easy to do. You can ask something that everyone has done, no one has done, or cares about either way. That's a waste of a turn and embarrassing, too.

But now, thanks to this list of interesting never have I ever questions; you'll never have to worry about your questions again. Each one of these questions is sure to lead to some interesting revelations about everyone playing.

Here are 5 interesting never have I ever questions:

61. Never have I ever wished I didn’t have to work for a living.

Who dreams of a life of accessible luxury and who enjoys work?

62. Never have I ever forged my parent’s signature.

The stories that come out of this are always great. We've all been there.

63. Never have I ever hide from a guest.

You're not honest if you've never pretended to be gone while there's a guest in your living room. There are just some people we're not ready to face at certain times.

64. Never have I ever thought of leaving my current job.

Everyone considers leaving their jobs if there's a more significant opportunity for growth out there.

65. Never have I ever hate my grandparents.

It can be pretty hard to hate our grandparents. They're so hard to resist because they're like the sweetest people ever.

Downloadable and Printable List of Interesting Questions

Here is a downloadable and printable jpg/pdf list of interesting questions (right-click the image and select Save Image As...):

Frequently Asked Questions

We've got all the answers to all of your questions.

When can you use interesting questions?

You can use these kinds of questions any time at all! They're interesting and exciting, which means anyone will be able to appreciate this. We all enjoy answering good questions here and there.

What are the most interesting topics to talk about that are good for late-night conversations?

When it comes to late-night conversations, the more profound questions you have, the better. When you touch on personal and deep, maybe even philosophical questions, it makes for a great night.

How do you know if someone is interested in your questions?

If they answer with more than a yes or no and go on to give more details about their answer, you know you've got someone very interested in what you have to ask.

How To Ask Interesting Questions

One of the great things about asking questions is how easy it is. Just follow these three steps.

Here's how to ask the best questions:

1. Ask questions that fit 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 too conservative with your friends.

2. Ask questions that fit the situation

Even if people like exciting 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 questions that fit the present discussion

Unless you're looking to go complete non sequitur, choose questions that slide easily into the discussion. Use conversation starters early, and then use others when the discussion is drifting in that direction.

More Best Questions to Ask

If you are looking for even more questions to build up your skills, Mantelligence has all you could need. Try these:

  1. When you want to get out of a discussion rut, try these random questions
  2. Get some crazy answers from unexpected questions with our weird questions to ask
  3. Want to give a great impression to new people? Use some funny get to know you questions.

In Conclusion

When you struggle to come up with cool questions to ask someone, it's probably because you want those questions to be interesting.

Thankfully, now you've got tons of questions to ask people in every situation so that you never have to have another bland discussion 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 pleasantly.

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