good questions to ask main post compWhether you’re on a date, making new friends, connecting with family, or vetting co-workers, sometimes getting to know someone isn’t as easy you’d expect.

We’ve all been there:

Racking your brain, trying to think of a conversation starter and all you can come up with is “How’s the weather?” or “What’s new?”

What’s even worse is being stuck on a date with nothing to talk about! Yikes!

I say, worry no more:

The key to making conversation or getting anyone to open up is knowing the right questions to ask.

Below, I’ve put together 75 thought-provoking, interesting and deep questions to get to know someone.

They’re questions that will ignite stimulating, personal conversations and will help you to build deeper connections with people.

75 Interesting, Deep and Thought-Provoking Questions to Ask to Get to Know Someone

These questions are powerful on their own, but I do have a few tips to help you get the most out of them:

Tip #1: After asking the question, give the person the time they need to answer. Don’t quickly change the subject or fire off another question.

Tip #2: Many of these questions will bring up sensitive material. If a question touches on their fears, missed opportunities, or anything else intimate, respond with compassion and sensitivity.

Tip #3: Match the question you ask to the current situation you’re in. For example, if you’re on a first date, don’t ask #21 What Makes You Cry? According to our dating expert Robin Sutherns, girls don’t like to cry on their first date.

Here are 75 of the best questions to ask someone to spark conversation and get them to open up:

Free PDF Bonus: Click here to get access to a free PDF that gives you all 75 Questions AND 25 exclusive Bonus Questions we didn’t publish below!

75. If you could bring one musician back from the dead, who would it be and why?

Music speaks differently to everyone.

The type of music a person listens to can tell you a lot about them. Asking this question, you’ll not only learn a person’s musical preference, but also who their all-time favorite band was.

The “why” of this question will also get you some pretty interesting responses.

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74. What do you define as “manliness”?

This is a great question to ask your father or son as it will reveal what they think it takes to be a man.

For an even more interesting conversation, ask a woman this question.

73. If you had to choose to live without one of your five senses, which one would you give up?

Which of the five senses could they live without?

If someone is touchy-feely, they’d most certainly leave touch intact. If they left out their eyes, then you know they could be excellent listeners. If they cut their sense of taste out, then you know they aren’t picky about where to eat.

72. If you could live in a book, TV show or movie, what would it be?

This simple question will tell you a lot about a person.

What genre did they choose? Romance? Sci-fi? Drama?

This is a great questions to get to know someone. Not only will you learn their preferred genre, it will also spark a very interesting conversation.

71. If you could get away with a crime, would you? If yes, what would it be?

This is one of the more interesting questions to ask as it explores the dark side of human nature by giving someone a “get out of jail free” card.

Will they commit the crime or choose not to?

The fun comes when people tell you what crime they’d commit. It has limitless possibilities, making it fun at parties and on dates.

70. What animal best represents you and why?

This is one of those good questions to get to know someone.

Boiling down one’s essence into a specific animal is a great way to understand how people see themselves.

Are their descriptions superficial, like the king of the jungle the lion, or do they reflect more personable qualities, like the loyalty of dogs?

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The king

69. Where do you see yourself in five years?

Sociologist Robert K. Merton coined the term self-fulfilling prophecy to explain how personal projection paints a complete picture of how people see themselves.

This one the better questions to get to know someone because while it comes off as a simple conversation starter, their answer will often reveal what’s most important to them.

Do they respond with something work related (I’ll be district manager)? Family related (I’ll be married with my first child)?

68. What do you define as a family?

Family means something different to everyone.

Whether their definition includes the classic family unit, or an extended definition involving friends and pets, you’ll open up a dialog that’s unique and potentially even controversial.

67. If you could live forever, how would you spend eternity?

This tried and true “all the time in the world” scenario is a classic get to know you question and is one of those good questions to ask almost anyone – even strangers – and you’ll always get their gears cranking for a thoughtful response.

How our downtime is managed often defines us, so by giving someone the option for unlimited time, we get to peek into their deepest desires.

66. How would you spend a billion dollars?

This is another classic “What if?” that can be asked to anyone (except billionaires). It’ll test the limits of what a person would do with a crazy amount of money.

It also helps to tell you what’s important to them. Would they donate to charity? Blow it all on their friend? Invest in stocks and bonds?

65. Why did you choose your profession?

Forget about asking someone, “Where do you work?”

Whether they’re driven by the money, a passion, a series of coincidences, or family, the answer to this question will give you an insight into their motivations for success.

A good follow up to this question is to ask whether they would quit their job and change their profession if they had the chance.

64. In what ways do you hold yourself back?

This is a highly personal question that should be reserved for close friends and loved ones. It involves a deeper introspection that strangers may not be comfortable revealing.

Not only will you learn more about the person asking this deep question, you’ll motivate them to grow and improve on a current setback.

63. What would you do if you were the president of your own country?

Note: If you don’t like talking about politics, avoid this question!

With that, it doesn’t directly ask, “What political party are you?” It instead asks a more important question, “What issues are most significant to you?”

62. How do you want to be remembered?

This is one of the most interesting questions to ask as it’s self-reflective and opens up a conversation about a person’s impact on others.

It will give you an insight into their ideals, morals and values. Do they want to be remembered as a family man, as someone who cured a terrible disease, or as a movie star?

61. If you could travel anywhere in the world, where would it be?

This question will tell you where someone thinks they would be the happiest.

The lucky few that actually answer, “Here,” are people you’ll want to always keep in your life.

60. If you could take only three items with you to a deserted island, what would they be?

What matters most to a person?

Are the items they choose based on survival, are they personal/sentimental, or are they both?

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What would you bring?

59. What book has influenced you most?

Like music, literature is very personal.

This is an interesting question to ask someone because it will tell you:

  1. What genres of literature they read. Is it historical fiction? Comedy? Fantasy?
  2. The book that has had a big enough impact on the person that it has altered their life in some way.

Their answer will tell you more about them and maybe even add a good book to your reading list.

58. In what ways are you a leader? In what ways are you a follower?

This two-part question is an introspective look into someone’s motivations.

You can find out if they are an introvert, an extrovert, or something in-between.

57. What was your dream job growing up?

We all wanted to be something unique growing up – a doctor, a zookeeper, a pilot, a wrestler, and so on…

As adults, do we still have those same dream professions?

Ask a friend or loved on this fun question to see how close to the mark they are, or what jobs they think are fun, important, and interesting.

56. If you could change one law, what would it be?

Stan Lee said:

With great power comes great responsibility.”

How would you make a difference in the world?

This thought-provoking question always produces a list of surprising answers.

Free PDF Bonus: Click here to get access to a free PDF that gives you all 75 Questions AND 25 exclusive Bonus Questions we didn’t publish below!

55. What’s your greatest failure, and how did you overcome it?

Our greatest accomplishments stem from our hardest falls.

A deeply personal question, this should be reserved for those you’re close with and should aim to motivate rather than knock down.

54. What’s your greatest achievement and how has it shaped you?

People love talking about themselves and especially about their past accomplishments.

This makes this question is one of the best conversation starters and will help you understand what they’re proud of and what motivates them.

53. If you could master one skill you don’t have right now, what would it be?

Knowledge is power.

This is a good question to ask to get to know your friends’ hobbies, their dreams, and what skill sets they respect.

You may even motivate them to start learning that skill or trade they’ve always wanted to know!

52. Which are you more likely to fight for, love or money? Why?

This is a lighthearted, fun question that will help you see what a person truly values.

Note: Most people will give you a quick answer so be prepared to respond with a “Why?” Their response will help you to understand the motivation behind their values.

51. What would be your “perfect” day?

Most people will look to their past to find an answer to this question.

Some have already lived their perfect day, and would love to recreate it. Others will take parts of their best days and patchwork them into one into one “perfect” day.

Either way, you’ll learn who and what is most important to them.

50. If you could have one superpower, what would it be and how would you use it?

This is one of the more fun questions to ask on our list.

Flight, laser-beam eyes, x-ray vision, invisibility, the power to freeze time: By choosing a single superpower, you can glean a bit of personal truth and desire from someone.

Voyeurism, power, strength, heroism, and a million other personality traits can be evoked by asking this lighthearted question.

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One superpower… so many choices

49. If you could speak another language, which would it be and why?

This simple question opens up discussions about traveling abroad, common interests, world cuisine, and trips around the globe.

If you want to get a feel for what cultures someone admires and where they could see themselves living it’s a great question to ask.

48. If you could time travel, would you go to the past or the future?

Do they like the way things were? Do they want something new?

This great conversation starter has the potential to stir up plenty of laughs or a serious discussion, depending who you ask.

47. Would you rather be a jack of many trades or a master of one?

Find out the difference between a person’s hobbies and their passions.

This question asks them to focus on whether they can choose a favorite, or if their interests are more diverse.

It can also tell you whether they’re more career or entrepreneurial minded. Entrepreneurs are inherently jacks of all trades, whereas, career minded people tend to be masters of one or a few skills.

46. What makes you happiest?

This overarching question is ambiguous enough to be a great question to ask on a first date, a solid interview question, or one of the more introspective conversation starters to use with friends, family, or acquaintances.

Since happiness is a universal, and what makes someone happy is so personal, it can help you quickly get to know someone.

45. How would your best friends describe you?

Your friends are a barometer for truth. They’ll be brutally honest about you, and you know it.

This question allows for a slightly more thoughtful answer than one could get asking them to simply describe themselves in their own terms.

44. What fad do you wish would come back? Which do you feel should stay gone forever?

Some trends should go away forever, like the now extinct pet rock. Others, like JNCO jeans are said to be returning to their previous glory.

This is a good question to ask at a party. It allows for hilarious comparisons about trends-gone-by and the ridiculous things we used to think were fun and fashionable.

43. If you could change one thing about yourself, what would it be?

The Greek philosopher Heraclitus of Ephesus once said:

Everything changes and nothing stands still.”

Our constantly evolving personal lives are determined by the choices we make on a daily basis.

Asking this deep question is a great way to gauge how others see themselves and what actions they’d take to transform their current self.

42. If you could change one event from history, what would it be?

Questions that give you the theoretical power to alter reality are a great way to find out what a person values on a more fundamental level.

The underlying question here is “if you could change history, would you?”

41. What is “home” to you?

Home isn’t always where the heart is.

If you asked 100 people this question, you will see a wide range of answers from, “a place to lie down at night,” to “anywhere family is.”

Constant travelers will have a very unique perspective on this question.

40. Who’s your personal hero?

This is the quintessential question to ask someone when you’re trying to get them to open up.

We often emulate our heroes and hold their values up as a template for our own. This question will give you a deeper understanding of someone’s personal values and beliefs.

Note: Employers will often use this question to get a feel for the character of new hires.

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Her hero

39. What are your three favorite albums? Why?

Music is a window to a person’s soul.

This question digs deeper than #75 because it requires them to choose 3 albums (and not just their favorite artist).

Are there consistencies in their musical preferences? Are they across the board?

Knowing what types of music people like will give you a great peek into who they really are.

38. What motivates you to succeed?

A more blunt way to ask this question would be, “what gets you out of bed in the morning?”

Knowing what motivates someone to succeed, and to work hard, will tell you what’s important to them. Is it family? Is it security?

PS: If you’re looking for motivation to succeed, check out the motivation section of our steps to success post.

37. If you could bring one fictional character to life, who would it be and why?

This is similar to #72 but adds a fun twist:

If you could bring any fictional character into YOUR world, who would it be?

It’s definitively one of the more fun questions to ask, but it will also give you an insight into what a person wants. Do they respond with a character from a romance movie (like Rachel McAdams)? Or do they respond with a superhero (like Superman)?

36. If you could choose your last words, what would they be?

Depending on who you ask, this creative question can yield serious, humorous, or personal results.

Your final words…

Their answer, and who it relates to, will tell you a lot about what’s important to them. Do they talk about their family? Their parents? Themselves?

35. What’s something too serious to be joked about?

Everyone has a limit to what they find to be funny.

This question is a great way to get people to open up and reveal their stance on sexist jokes, dark humor, etc.

34. If you could fight anyone in history, who would it be?

Did you ever want to punch an unworthy celebrity? What about going toe to toe with a long-dead dictator?

This question always creates a really fun conversation full of laughs and unique selections.

33. Would you rather explore a new planet, or the deepest parts of the ocean? Why?

Here’s another fun question that usually starts a very interesting conversation.

Their initial response (new planet or ocean) doesn’t reveal much… both are extreme in their own regard. The conversation gets interesting when they answer the “why”.

32. In what ways are you the same as your childhood self?

This this seems like a simple question, it will actually tell you a lot about a person.

It forces them to reflect, and express, the personality traits that have stayed constant throughout their life.

If the list they give you is short, they may be a person who’s constantly reinventing themselves.

31. What dream that you’ve had has resonated with you the most?

Some say dreams embody our hopes, fears, and deepest fantasies.

Whether or not you believe this, this unexpected and interesting question will always give you a memorable response.

30. What’s the best concert you’ve ever been to?

A classic question to ask that never gets old, asking someone about their favorite live performance is a great way to find out what they like and dislike.

Was it a festival or an intimate show, or a loud, packed event?

Getting to know all the details will help you form a bond through swapping stories about your own favorite concert.

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What was your absolute favorite concert?

29. What single message would you send to an advanced alien species?

This is one of those unique, interesting questions to ask people that will get your some extremely interesting responses.

Would they send a message of peace? Would they ask to be “beamed up”?

28. What’s your favorite comedy movie?

What makes different people laugh can vary greatly.

Some people prefer slapstick comedy (movies like Monty Python) while others prefer dry humor (movies like The Big Lebowski).

This is a great question on a first date as it will tell if you and your date have a similar sense of humor.

27. How would you survive a zombie apocalypse?

If you’re at a bar with friends, it’s fun to speculate how each of you would function within a zombie-survival-group.

It’ll get you some fun responses, but will also tell you how prepared they are for a real-life disaster like hurricanes and fires.

26. If it were possible to colonize Mars in our lifetime, would you go? Why or why not?

Here’s another question that gauges a person’s adventurousness.

Their eagerness to leave behind everything they know could be telling. You may also get someone to open up about their hopes and anxieties about travelling (whether it’s to going outer-space or cross-country).

Free PDF Bonus: Click here to get access to a free PDF that gives you all 75 Questions AND 25 exclusive Bonus Questions we didn’t publish below!

25. If you could play one instrument you aren’t able to now, what would it be and why?

Music is always one of the best conversation starters.

This is such a good question to ask because neither you nor the person you’re talking to needs any musical talent.

By indulging in the idea of playing an instrument, you’ll soon be having a conversation about your favorite songs, concerts, and musicians.

24. Would you rather live in the city or the woods? Why?

Usually, this question will be asked as, “Would you rather live in the mountains or by the beach?

By asking them to choose between the city and the woods, you’re forcing them to decide between two stark opposites: the hustle and bustle of the city or calm and tranquility of the woods.

This is another great date question… does their living preference align with yours?

23. What teacher inspired you the most? How did they?

We all remember that special teacher that either pushed us harder than the rest, or inspired us through their support and kindness.

The “how did they” part of the question will help you to understand how the person is best motivated to succeed (by pushing them or through support).

22. What’s your favorite holiday and why?

The holidays always evoke the strongest emotions and create the most treasured memories.

While this seems like this question won’t help you get to know someone, it actually reveals a lot about their culture, beliefs and family ties.

What type of person are they? Thanksgiving (family oriented)… or New Year’s Eve (party/celebration oriented)?

21. What makes you cry?

This question will certainly bring the tone of a conversation down a few notches, so reserve it for those you’re close with and use it with caution.

It’s a great question to ask to get to know someone on a deeper, more emotional level.

When someone reveals what makes the cry, they can often feel very vulnerable. Empathize and relate to them by providing your own answer to the question.

20. If you were on death row, what would your final meal be?

Variety is the spice of life, but when it comes down to it, we all have that one dish that’s irreplaceable in our hearts.

This isn’t a “get to know you question” but is a lot of fun.

If you want to dig deeper with this question, follow up with, “Why would that be your last?” You might get something boring like, “It’s my favorite” but you may also get something revealing like, “That was my mother’s signature dish.”

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The last meal

19. What’s your fondest childhood memory?

Questions about childhood memories always bring us closer.

Someone’s retelling of a camping or fishing trip with their grandparents will evoke a relaxed, but extremely personal conversation.

18. Which one of your friends would make the best U.S. President and why?

The answer to this question will tell you which friends a person admires the most (and usually which they admire the least).

Explaining the “why” will give you a better understanding of who the person has chosen to surround themselves with. As Karen Marie Morning wisely said:

Who and what we surround ourselves with is who and what we become.”

17. If you could abolish one piece of modern technology, what would it be and why?

Asking someone to abolish a piece of technology is a great way to find out what modern accommodations annoy them.

If they respond with “cell phone,” then you know that when talking to them, you should turn your Facebook notifications off and pay attention!

16. If it were possible, would you own a pet dinosaur? If so, which one and why?

A good dinosaur question always teeters the line between silly and scientific.

You can simultaneously get a feel for someone’s creativity, their knowledge of science, their adventurousness, and their practicality in just one simple and seemingly random question.

15. If you were head of a major TV station for one day, what would you play?

Apparently, you are what you watch.

Your TV watching habits reveal a bit about your type of humor, your penchant for action, your attention to detail, or your lack thereof.

This question will usually spin into a conversation about movies and TV shows you both love.

14. If you could choose how you die, how would you go out?

This is a fun question to ask that almost always turns into an interesting conversation.

Would they choose to go out in a reckless blaze of glory, or surrounded by loved ones after a perfect day?

13. If you could bring back anyone from the dead, who would it be and why?

Long deceased musicians, artists, scientists, and family members have all inspired us through their works and actions.

What would Nikola Tesla say about the state of energy and manufacturing if he were alive today?

Would your grandmother be proud of the person you’ve become?

This question sparks fun and often deep conversational possibilities.

12. If you could speak to everyone in the world at the same time, what would you say?

This question often reveals how thoughtful someone is in their actions.

Would they seek to unite the world through a message of peace? Would they just blurt out a simple joke to get the whole world laughing?

Many will think this question through and respond with their personal philosophy on the state of the world and how they’d seek to improve it.

11. If you could use technology to do one thing, what would it be?

While this is a simple question, it will reveal a lot about a person.

Would they choose to use technology to make improvements to the environment? Health care? Transportation?

A response could be, “I would use technology to cure cancer.” This broadly tells you what’s important to them (improving health care) but also specifically what they care about (curing cancer).

10. What’s the craziest thing you’ve ever done?

This is a fun question to ask and will introduce you to a person’s wilder side.

Do they live life on the edge… their “craziest” being skydiving or shark diving? Or are they more reserved… their “craziest” being travelling out of the country or hiking a mountain?

Regardless, since people love to recount their adventurous moments, this question almost always leads to a fun, engaged conversation.

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Crazier than skydiving?

9. If you could have dinner with any one person, living or dead, who would they be and why?

A time-tested and thoughtful question, that asks about a person’s “dream dinner.”

This question gets people to open up and talk about someone they admire, someone they miss, or someone they’re curious about in intimate detail.

8. If you could speak another language, which would it be and why?

This simple question opens up discussions about traveling abroad, common interests, world cuisine, and trips around the globe.

If you want to get a feel for what cultures someone admires, and where they could see themselves living, this is a great question to ask.

7. If you had a week to live, how would you live it?

With only a week to live, your priorities become crystal clear.

Would you burn all your bridges? Right all your wrongs? Spend time with family?

The goal of this question is to see how happy someone is with their current situation and what they would change about their behavior if they knew their time was limited.

6. If your house was burning and you could only save one item, what would it be and why?

This question directly asks, “What’s your most important possession?”

Indirectly, it asks what’s generally most important to them. The possession that they choose will reveal what they care most about.

Is it:

My daughter’s doll? My laptop? My wedding photo book?

5. How do you define love?

Love is one of those intangible concepts that everyone experiences in their own unique way.

Asking them to put “love” into words will draw out a thoughtful conversation based on personal experiences, losses, heartaches, triumphs and victories.

This is one of those good questions to ask a partner, a potential love interest, or even a friend or family member.

4. Which 1900’s era would you travel back to? Why?

Each of the 1900’s eras had its own unique flavor:

The 20’s brought huge social and political change like the women’s rights and prohibition. The 80’s brought grunge and what can only be described as 80’s fashion.

Whether or not they realize it, most people associate with one of these eras. Asking someone this question sparks a fun conversation about the ideals and aspects that they loved about the era.

3. If you could have the answer to any question, what would that question be?

This is the one of the best questions to ask when you’re trying to get someone to open up.

It gives anyone the space to talk about the biggest unanswered question they have about their past, present or future.


Their response is very likely going to be something deeply personal. Be prepared to be supportive and to respond with your own answer to the question.

2. What are you most grateful for?

This is one of the most classic questions to ask someone.

On the surface, it seems like the response won’t be revealing, but their answer will tell you exactly what’s most important to them.

Are they most grateful for their family? Their health? The roof over their head?

1. What words of wisdom would you pass onto your childhood self?

This is probably the best questions to ask to get to know someone. It can reveal a great deal about a person like:

  • Their most valuable life lessons
  • Their biggest regrets
  • The career path they wish they would have taken
  • Opportunities that they’ve missed

This question gives you a better understanding of someone’s past and shows you the wisdom they’ve garnered with age.

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With age comes wisdom

In Conclusion

Through the simple act of asking open-ended questions, we give others the opportunity to share their stories and experiences, hopes and dreams, and their fears and triumphs.

If you’re looking to get to know someone on a deeper, more meaningful level, start with one of these 75 great questions to ask.


Comment below with your favorites and any other great questions to ask people!


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Official GDC | Martin Pulaski | Eric Kilby | CSITDMS | Gareth Simspon | DVIDSHUB | Danteg | Amelie123 | ToddonFlickr | Graham Crumb