Best Questions to Get to Know Someone

Best Questions to Get to Know Someone

Can you ever really know someone? That’s a loaded question! The only person who knows you best is you, right? Are you willing to open up to others about who you truly are? Are there some things about yourself that you hold back for fear of rejection or bringing up bad memories? Or do you think it is good to share with others as a sort of therapy for them and you?

People surround you daily, but do you really know them? Maybe you want to share yourself with another person. Perhaps you want them to share themselves with you. Whether you are meeting a new person or are trying to get to know an acquaintance better, you’ll need some questions to ask them. These aren’t your regular “fluff” questions. These are questions that will spark conversations into more in-depth topics that can help you to understand who they are. 

So, as you approach getting to know someone better, we hope these questions can help you to find out about people’s values, priorities, and paradigms. This can help you in many situations, such as choosing your friends, choosing who you will continue to date, choosing who you will hire, choosing how to best care for children, choosing how best to serve those around you, and so many more.


Best Questions to Get to Know Someone

Here is a simple way to get to the right kind of questions based on the situation you are in. If you are romantically interested in someone, maybe head to the love interest questions, but definitely stay away from that category when you are choosing someone to hire! Haha! I hope you enjoy the collection of questions and that they help you connect in more profound, healthy ways with those around you.

EasyCasualLove InterestPersonal


Easy Questions to Get to Know Someone

1. What is your favorite way to spend a weekend?

Relaxing on the sofa with a tub of ice cream or roughing it up on a camping trip with your buddies?

2. What’s your go-to Starbucks drink?

The follow-up question to this goes in the ‘love interest’ category. *wink, wink*

3. What type of music are you into?

This one’s an easy conversation starter. Who doesn’t love music?

4. What’s your favorite pastime?

The answers to this one are so general. You can’t go wrong.

5. What is the last book you read? What was its plot?

Everyone loves a good murder/mystery novel. Just be sure not to give away any spoilers!!

6. What was the last show you binge-watched?

There’s nothing like sharing the excitement of your fave shows. This also happens to be one of the most comfortable topics of conversation.

7. What’s your favorite ice cream flavor?

There’s cookie dough, strawberry sherbet, chocolate fudge, and so much more!!!

8. What is your ideal vacation?

The clearest blue-water beaches on Earth or a weekend in a big city you’ve never visited before?

9. Are you a podcast person? If so, what kinds of podcasts do you enjoy?

With all the streaming services nowadays, there’s a podcast about practically anything and everything.

10. What’s your favorite holiday, and why?

And no, your own birthday doesn’t count.

11. In the summer, would you rather sleep with the window open or blast the AC?

This all depends on where you live. Those Alabama summers can get deathly hot.

12. What’s your celebrity crush?

This one’s easy enough. One or both of the Hemsworth brothers, a member of the Hogwarts trio that we all fell in love with as kids, JB, JT, or J-Lo… Hollywood is a big and beautiful place.

13. Do you like going to the movies or would you prefer to watch a movie at home?

This could also be followed up by a ‘love interest’ question.

14. What song can you never resist the urge to dance to?

For some folks, it’s Disco, for others, it’s Tango. Personally, I like me some good old fashioned mainstream 80’s power ballads.

15. What’s your favorite meal of the day?

Breakfast is for the best of us, lunch is a midday crunch, and dinner is the winner.

16. How many animal accounts do you follow on Instagram?

You can surprisingly tell a lot about a person by their answer to this question. *Enter fluffy Pomeranian puppy named Snuggles*

17. When you were a kid, did you eat the crusts on your PB&Js or not?

Did you also secretly feed them to the dog so your mom wouldn’t find out?

18. What would your ideal birthday look like?

Are you the type that’s going to spend your entire birthday weekend partying at clubs and karaoke bars with your BFFs or taking it easy at home with a good book, your favorite HBO series, and an entire tub of your favorite brand of ice cream?

19. What’s your favorite type of exercise?

Some people are more into heavy cardio, and others may enjoy intense muscle burn. There are a million and one fun ways to keep your body in shape!!

20. What is the best joke you’ve ever heard?

Something about getting to the other side…

21. What phone app do you use the most?

Want to find out with one question what someone prioritizes? This is the one for you.

22. What’s your favorite board game?

Does anyone nowadays still plays those things?

23. Would you rather cook or order takeout?

Sometimes all it takes is one recipe gone right, and you’re a home-cooker for the rest of your life.

24. What’s one product that you could not live without?

How do the minimalists do it?

25. If you could have any exotic animal as a pet, what would it be?

Lions and tigers and bears, oh my!!!

26. Do you prefer the beach or a community pool?

We probably all have traumatic memories of both.

27. What’s your dream job?

Achieve big. Dream bigger.

28. Do you have any pet peeves?

Here are a few examples: chewing nails, smacking gum, breathing too loud.

29. Do you/did you ever play sports?

This question will usually bring a smile to their face as their head fills with memories.

30. What’s your favorite nonalcoholic drink?

Must they have their daily dose of soda, coffee, tea, or are they a juicy person?

31. If you could have any kind of car, what would it be?

Can you tell a lot about a person by their car? Are they risk-takers, practical, rugged, high-maintenance, or cheap?

32. What sites do you like to visit the most?

Where a person goes on the web will tell you a lot about their interests right upfront.

33. What is your favorite type of dessert food?

Are you more of a gooey chocolate brownie person or a sweet lemon meringue pie person?

34. Where is the most interesting place you’ve ever visited?

If they say their living room couch, you may want to move along to get to know someone else.

35. What’s the best bargain you’ve ever found?

Couponers and bargain-hunters will be so happy to answer this question! They love sharing their strategies, too.

36. If you could choose one age to be permanently, how old would you be?

This answer will probably change a lot for someone throughout the course of their life.

37. If you could choose one fictional place to go, where would it be, and why?

This could be from anything fictional; video games, books, movies, or their own imagination!

38. What is the worst piece of art you’ve ever seen?

Should we cue the laughter or the confused looks or the gagging sounds?

39. What is the best piece of art you’ve ever seen?

This has got to be something that just took their breath away or spoke to them deeply.

40. What is one popular show or movie that you refuse to watch, and why?

Not everyone is mainstream with their viewing habits. Everyone’s standards are bound to be different.

41. What pets did you have when you were a kid?

This is probably the easiest question in here because it doesn’t approach anything controversial unless you want to argue about whether cats or dogs are better pets.

42. Have you ever had anything really lucky happen to you?

It could be something that was perfect timing, or it may be a time when they won something.

43. What is the best thing that’s happened to you in the last few weeks?

Positive things sometimes don’t get noticed or remembered as much as they should, so it’s important to help people remember.

44. What is the best outfit or piece of clothing you have ever had?

This one may be hard for some people to remember, or maybe they have had too many great clothes to come up with just one.

45. If you could become magically famous, would you want to?

There are pros and cons to being a superstar, but is the glamour worth the risks?

46. If you could have any superpower, what would it be?

With the countless hero/villain characters out there, it isn’t hard to gain inspiration for a catchy name and an out-of-this-world set of abilities.

47. What would you consider your spirit animal to be?

This might take a little thinking.

48. If you see a puddle, do you walk around or step over it?

This is about as random and easy as it gets.

49. What would you name a country you owned?

This might not be a very easy question.

50. Do you believe in any conspiracy theories?

The truth is out there…


Casual Questions to Get to Know Someone

1. What are your three favorite tv shows?

There are so many out there now! This includes streaming services’ original shows.

2. Are you related to anyone famous?

This can be anyone from history, too. How well do you know your family tree?

3. Have you ever met anyone famous?

Listening to the way this person speaks about famous people will tell you a lot about them.

4. Do you like to people watch? Why?

You could also dig a little to find out where they enjoy doing this the most? What’s the weirdest thing they’ve ever seen someone doing/wearing?

5. Do you have any songs completely memorized?

Bring on the playlists and karaoke with your eyes closed!

6. What skill would you like to perfect?

Yes, you can say nunchuck skills!

7. What genre/mode of art do you enjoy the most?

Paintings, dance, poetry, carvings, sculptures, and so much more bring beauty to our human experience. 

8. What is something you wish you knew more about?

Unless you are a veritable Renaissance Man, there is always more to learn in life. What do they wish they could learn more about?

9. What’s one unsolved mystery/question you wish you knew the answer to?

This can be anything from historical events to the mysteries of space or the heavens.

10. Besides your birthday, what is your favorite day of the year? Why?

There are people who, on any given day, can tell you how many days are left until Christmas!

11. Where is the farthest you’ve ever been from home?

Are they a homebody or full of wanderlust?

12. What trend, style or fad would you love to see make a comeback?

Bell bottoms anyone? Baby doll heels? Lederhosen? Blue eyeshadow? Parachute pants? “Valley Girl” accent? Just have fun with this one!

13. Where do you think the most relaxing place to go would be?

Some people picture doing nothing as relaxing. Others have to be doing fun stuff to feel relaxed. Find out what others do for relaxation with this question.

14. If you had to lose all your senses but one, which one would you choose to keep?

There’s a level of introspection required for this one.

15. What is something you are looking forward to in the next few months?

People love talking about their upcoming plans, so this is an easy one to get the other person talking.

16. What is an annoying thing that you see other people do?

Will it be chewing with the mouth open, picking the nose, biting the nails, or something else?

17. Where do you get your news?

Want an easy way to spark up a conversation with a stranger without seeming too overbearing or weird? This is the question for you.

18. If you had three wishes from a genie, what would they be?

Answers to this question can get oddly specific and revealing. Don’t take them too seriously… or maybe do??

19. If you could start a business of your own, what would it be?

Where are there holes in the market? What consumer demand is currently unfulfilled?

20. What famous person from history would you want to spend a day with?

History meaning pre-Harry Styles…sorry ladies.

21. Do you hit the snooze button or wake up to your first alarm?

There are two types of people: those with two alarms and those with twenty.

22. Would you rather be covered in fur or covered in scales?

When you reach that awkward pause in the conversation, all you can do is get creative.

23. Who would you want to play you in a movie of your life?

There are so many eccentric actors out there; you’re bound to find at least one who’s as whacky as you.

24. What is your favorite movie and book? Why?

If you have never heard of the book or movie, it can either be an exciting or boring answer. 

25. When making a PB&J sandwich, do you put the peanut butter or the jelly first?

Next time you make your lunch, pay closer attention. You never know when you’ll get asked a random question like this by that weirdo in the cubicle next to you.

26. What, if anything, would make you walk out in the middle of a movie?

Some subtle Marxist nuance, a little suggestive socialism? Movies explore a wide range of themes nowadays, but not all of them are worth examining.

27. What fictional character do you relate to?

Pop culture is full of lovable, relatable, and quirky characters to identify with.

28. What celebrities do you “stan”?

Yes, people like Kim K and Colton Underwood “technically” count.

29. What’s the best Halloween costume you ever wore as a kid?

We all have that one Halloween that will always be remembered.

30. If you could own a mythical creature, what would it be?

How about a griffin? A dragon? Some super cute talking squirrels?

31. Would you rather have your dishes or your clothes be magically cleaned?

Never spend money on laundry detergent or dish detergent? That’s the real question.

32. Do you enjoy watching or playing any particular sports?

This is probably one of the most harmless questions in the book. Plus, it helps you to figure out if you have anything in common.

33. What’s your favorite food?

Basic and to-the-point. Food talk is the easiest talk.

34. If you could be from any foreign country, what country would it be?

Opt for something a little different and creative.

35. What job do you think you’d be terrible at?

This will definitely get your conversation partner laughing at themselves, which automatically establishes a more comfortable atmosphere.

36. What’s your favorite color?

Yeah, it’s basic. But basic works sometimes. Follow up by asking them why their favorite color is their favorite. More often than not, there’s a story there.

37. What movie title best describes your life?

This is a good way to get someone self-reflecting and poised for further discussion about pop culture.

38. If you didn’t have to sleep to survive, what would you do with all that extra time?

Would you make an alter-ego for yourself like Batman, or would you take the opportunity to watch every show and read every book you own?

39. What do you think you could give an hour-long presentation on with zero preparation beforehand?

We are all experts on something.

40. If you suddenly became a master at woodworking, what would be the first thing you’d carve?

This question is pretty random, but people generally dig that.

41. What’s something you’re interested in that most people haven’t heard of?

We here at EndangeredEmoji totally get weird and obscure interests. In fact, we actively encourage everyone to have them.

42. What’s the best book or series you’ve ever read?

If one or both of you is a bibliophile in the slightest, you’ll probably be intensely discussing this topic for a long while.

43. What’s the most impressive thing you know how to do?

The answers to this one can get pretty cute, especially when your conversation partner tries to show you their amazing talent right there in the middle of the living room.

44. What’s the best thing that happened to you last week? What’s the worst thing?

Kind of random as an ice-breaker, but hey, it’s something to talk about.

45. In your opinion, what are some small things that could totally turn a crappy day into a great one?

Finding a lucky penny or getting complimented by a stranger… some things just turn a frown upside down.

46. What does your ideal weekend look like?

Whether it’s vegging out on the couch with some dope snackos and the most binge-able TV show or trekking it up the backside of a mountain, we all have our preferences.

47. What’s one popular TV show or movie that you absolutely refuse to watch?

Sometimes you just have to put your foot down and say no to the status quo.

48. Where is the most relaxing place you’ve ever been to?

We’ve all got a living room sofa, but maybe try and get a little more creative answering this one.

49. What’s something you’re most likely to become famous for?

Whether it’s TikTok, writing, music, or art, everyone has their niche skills and talents.

50. What city do you dream of living in?

You can come to understand a lot about a person based on this question. Places often tell about the people in them.


Love Interest Questions to Get to Know Someone

1. What’s one thing about you that you never hope changes?

Learning what value the person sees in themselves can make them more or less attractive to you. Are they proud or humble?

2. What would be a good rom-com movie title to describe your love life best?

They can make one up. Get those romantic, creative minds working.

3. What’s the best thing you can think of to start your day well?

According to an old commercial jingle, “The best part of wakin’ up is…”

4. From one year ago, how has your life changed?

We are looking for the good, the bad, and the ugly.

5. What is something you wish you didn’t know?

Ooh! How deep do you want to get with someone you like?

6. What’s your dream vacation?

Have they ever been there, or do they plan to go someday? Do they want to go by themselves or with their significant other?

7. If you could choose anywhere in the world to live, where would it be?

Find out where your potential future love interest wants to end up & why. If things go well, you could end up there with them!

8. When was the last time you climbed a tree or rode a bike just for fun?

Nostalgic feelings can easily make you feel closer to someone.

9. What do you love most about where you grew up?

Once again, delving into the past is an excellent way to tell you if this person is into you & willing to open up.

10. “You are most likely to be famous for ___________.”

Are they likely to fill in this blank with something great they did or something terrible they did? It’ll be interesting to find out.

11. Where is the most romantic place you have ever been to or would love to go to?

Here’s a subtle way to start a discussion about your future travel plans with this cute person you are flirting with.

12. What’s the most heartwarming story you’ve ever heard or thing you’ve ever seen?

This allows the person to get in touch with and open up about their gentler side.

13. Is there anything you like to insist on doing “the old-fashioned” way?

Some things are just too good to be changed! Does this person like change or not?

14. Would you rather go whitewater rafting or hang gliding?

Find out how adventurous they are and maybe plan some future dates with this one.

15. What do you do to relax after a hard day of work?

If this person could become part of your life, how will their daily routine match up with yours?

16. What does your ideal weekend look like? What would you do?

Hopefully, it will include you…

17. What is one thing you really want to buy, but can’t afford yet?

Money questions are essential to get out of the way early because money is the number one cause of divorce. Yikes!

18. What are some of the small things that make your day better?

Do they focus on little tender mercies daily, or are they noticing the simple beauties and joys around them? Will they notice the little sweet things you want to do for them to make their days better?

19. If you could teach your future child one lesson, what would it be?

A subtler (and notably less creepy) take on the statement: I want to have babies with you.

20. What is your deepest fear?

This is a pretty intimate question, so phrase it carefully.

21. Do you believe in an afterlife?

Make sure you and your prospective significant other are on the same terms when it comes to eternity. It’s kind of a big deal.

22. Do you think it’s a good idea to do one thing a day that scares you?

Make a bucket list, check things off one by one, fall in love, etcetera, etcetera…

23. How do you interact with someone who disagrees with you?

This is an ESSENTIAL topic to cover while dating.

24. If today was your last day on Earth, what would you do? Who would you spend it with?

If you’re looking to get some emotional answers out of your SO, this is a good question.

25. What’s your ideal first date?

There’s no harm in using this as a way to get someone to go out with you.

26. At a party, are you the social butterfly or the wallflower?

Get to know whether someone is naturally social or naturally introverted without asking them directly.

27. Do you have a relationship deal-breaker? What is it?

Make sure to be sensitive to this question as it may bring up unwanted feelings from past relationships.

28. Are you more into brains or brawn?

Hopefully both! 🙂

29. Would you ever take someone back that has been unfaithful to you?

This question will be able to help you understand what kind of person they are. Are they quickly forgiving? Will they even forgive at all? Or are they the vengeful type?

30. If you could change anything about yourself, what would it be?

Nobody’s perfect, and learning about someone’s flaws is sometimes the best way to understand how they see the world.

31. Do you have a “type”?

Maybe your partner will surprise you with this one.

32. Do you think personality matters more than looks?

When you know what someone really prioritizes, you can become a lot closer to them.

33. What qualities do you most look for in a long-term relationship?

There’s a lot of fish in the sea, but just remember that no one is perfect.

34. What is something you think is true about me that you’ve never asked to confirm?

This will help you get to know each other on a much more personal level.

35. Have you ever been in love before?

Make sure you trust someone before you ask them this.

36. How do you think the next ten years of your life will look?

This is a good way to focus your conversation on the things that matter.

37. How do you normally spend an evening?

There’s no better way to get to know someone than to spend time with them, which is why this is one of the best questions you can ask.

38. What are your career goals? Do you have a retirement plan?

There’s no better time to talk about important things than the present.

39. When it comes to Valentine’s Day, are you more of a simple love-note and flowers with Netflix type of person or a fancy dinner with assorted cheeses and wines type of person?

The way you spend a holiday like this can say a lot about who you are.

40. Are there any experiences you’ve had with a past relationship that you’ve learned a lot from?

You don’t have to pry too far into your significant other’s past, but it is necessary to understand some of their past experiences to become closer.

41. In a relationship, do you think it’s important to schedule time to spend together each day?

To maintain a healthy relationship, you have to be on the same page about what you’re both willing to give to it.

42. Are you the type of person that takes the words “I love you” very seriously, or is it a phrase you use openly and often?

Though this isn’t an essential question, it’s nice to understand how your partner identifies their feelings for you.

43. Are you someone willing to sacrifice to keep a good relationship going?

Really, the word “sacrifice” can mean a billion different things.

44. Would you rather forgive quickly and without much conversation or do you think it’s important to dwell on your emotions for a bit before approaching a sensitive topic with your partner?

If you’d like to avoid a few potentially harmful misunderstandings and hurt feelings, this is a good question to ask your partner.

45. Do you think lies have any place in a relationship, even if they’re kept for the benefit of one or both parties?

You’ll probably get more of a situationally-based answer for this question, but it’s still intriguing.

46. Do you have high hopes for the future, or are you more of a gloom-and-doom cynic?

This is an easy way to find out if you and your partner balance each other out in terms of attitude.

47. Do you believe there is a balance between maintaining your happiness and that of your partner? If so, what would that balance look like? Are you responsible for their happiness, to some degree?

This is definitely not a one-word answer. You’ll have to get pretty introspective and honest with your significant other.

48. Do you have theories as to how you’ll die?

This is morbid, but only if you don’t ask it with a specific intonation.

49. Do you believe in serenading your husband/wife/partner?

Self-incited humiliation in the name of love = devotion, right?

50. Would you consider me to be your best friend?

Falling in love with someone you already love is the best thing ever.


Personal Questions to Get to Know Someone

1. How would your ten-year-old self react to the place you’re at now in your life?

This may or may not send someone spiraling into an existential crisis, so just watch out for that.

2. Would you consider yourself to be fulfilled in your life? Why or why not?

Refer to question 1. Maybe have a therapist on-hand.

3. Are you more of a “work to live” or a “live to work” type of person?

There’s nothing like a good old ice-breaker to reignite the awkward tension. Only use this when you’re nice and comfortable with the other person.

4. What have been the best and worst career decisions you’ve ever made?

Hopefully, they can laugh about the mistakes they made as an intern now.

5. Were you close with your family growing up?

If you really want to get to know someone, talking about your family can be one of the best ice-breakers… or one of the biggest turn-offs.

6. Do you have any siblings?

Sharing some of your favorite memories can be one of the best ways to have a good conversation with someone.

7. Are you habitually late or early?

How someone manages their time can tell you a lot about the rest of their priorities and how they run their affairs.

8. What is one quirky thing about you?

One of two things will probably happen in response to this question. They’ll either shy away from answering, or they will spill the beans.

9. What is one thing about you that you think bothers other people the most?

This will make even the least introspective person step outside themselves for a minute. On the other hand, their answer may show you how clueless they are about how they affect others.

10. What career do you think you would be terrible in?

Admitting faults and areas of lack are a sign of humility.

11. What’s one thing in your life that you are sure to do, or that you are absolutely determined to do?

This will give you insight into the level of drive this person has to succeed in life as long as they can follow through with what it takes to get those things done.

12. What would be a good movie title for your life?

Insidious? American Graffiti? Hairspray? Can’t Buy Me Love?

13. How do you cope with work stress?

This is a good question to help get to know your coworkers better.

14. What has had the most significant impact on your career choice?

This is an excellent way to find out more about the people you work with.

15. What’s your favorite way to spend time with your family?

You can get into some good, substantial conversation with this one.

16. What makes you nostalgic?

It could be the smell of fresh-cut grass or the sound of Christmas music, something weird or something common. Everyone has that one thing that

17. What is your biggest waste of time?

Confession time!

18. What’s worth spending extra money on to make sure you get the best quality?

Money questions will get a different answer from everyone because of differences in priorities, so this is a good question for getting to know what’s important to people.

19. What personality traits do you share with your relatives? Do you think you’re more or less like other members of your family?

If you really want to get into hard, introspective conversations with someone, this is a good question to start with.

20. When was the last time you had your opinion changed & what was it about?

This one can be quite personal. Opinions are sacred things, so tread gently.

21. What was one of your favorite bedtime stories growing up?

Dragons, knights, and cracked eggs had a way of teaching us all some pretty invaluable life lessons.

22. How did your parents/grandparents meet?

Retelling their parents’ stories always tends to bring a smile to a person’s face.

23. What is your definition of success?

Not all that glitters is gold.

24. Who is one person who has impressed you with something they have accomplished with their life?

This shows you what they aspire to be and what they feel are important priorities.

25. Are you religious or spiritual at all?

This is a tricky topic to navigate in light conversation, so make sure to be understanding of other people’s views.

26. What accomplishment have you achieved in the last year that you are proud of?

This will get a person thinking about what they’ve achieved in their lives

27. If you won a million dollars, how much of it would you donate to charity?

Nothing like guilt-tripping your friends into philanthropy.

28. What is the best thing a person can spend their time on?

Are they into helping others, being with their family, self-improvement, having fun, or spiritual stuff? You’ll be able to tell a lot about a person from their answer to this question.

29. Who is your role model?

They may choose celebrities, historical figures, entrepreneurial thirty-somethings, astronauts, and so many more. This world is full of incredible people.

30. What are your political views?

Yes, this is a VERY personal question.

31. Do you live by any kind of personal motto?

Putting a definition to your life can give it a little bit more purpose.

32. If you could snap your fingers and instantly solve a world problem, what problem would you choose to eliminate?

Get to know the save-the-world side of someone, and you’ll like them all the more.

33. Have you ever lost a friend? If so, what happened?

Make sure to be considerate of people’s boundaries and don’t ask this question if the situation isn’t appropriate.

34. Are you closer to your Dad or Mom? Why?

This can bring up great stories, but it is also a gentle question to ask if their parent has passed away.

35. What is something you have done that makes you feel accomplished?

Get to know what great things they have done as well as their priorities. 

36. How have you turned your weaknesses into strengths? Do you believe there is one best way to accomplish this?

As long as you don’t ask this the way a boss would in a job interview, you can get into some pretty deep conversation.

37. How do you compromise your beliefs about the cosmos and the divine with the laws of science and the every day realities?

Don’t go spiraling into an existential crisis or anything drastic, and make sure your conversation mate doesn’t either.

38. Do you believe humans are better at creating or destroying?

Defy all the unwritten laws of small talk and just dive down right to the nitty-gritty with this one.

39. What three words would you use to describe your outlook on life?

This will get your conversation partner thinking.

40. How different was your life one year ago?

There’s something strange and wonderful about looking back and reminiscing on the past.

41. What are some things you’ve had to unlearn?

Everyone develops bad habits or self-destructive tendencies throughout their life (mostly in high school), so it’s useful to self-reflect.

42. What’s something special about the place where you were raised?

Questions like this hit a little closer to home and tend to get people to dig a little deeper.

43. Is there a fictional place you would absolutely love to visit?

The places in books, movies, and video games are all so epic. Plus, you get to find out a little bit more about what your conversation partner is interested in.

44. What’s the most heartwarming thing you’ve ever seen?

There are plenty of choices like viral puppy videos, grandpa serenading grandma at the retirement home, or global Christmas initiatives. The world can be a pretty good place.

45. What’s one job do you think you would be really good at?

Whether it’s a criminal investigator, medical professional, or ice cream parlor employee, everyone is good at something.

46. What pets did you have growing up?

Animals are always a safe and interesting conversation topic, and there are usually some pretty funny, heartwarming stories accompanying the answer to this particular question.

47. What’s your idea of the perfect adventure?

We human beings take our adventures very seriously.

48. What’s one thing that you really want to do but don’t have the money for yet?

Get to talking about aspirations, and you’ve reached the peak of high-quality conversation.

49. What’s the luckiest thing that has ever happened to you?

Sometimes, you just get lucky.

50. In your opinion, what’s the worst/most annoying habit another person could have?

Watch out; these can get creepily specific.