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98 Wonderful Questions To Ask Friends - Have Really Great Conversations

Looking for questions to ask friends? There's no doubt: Even in the best of friendships, occasionally you or your friend will run out of things to say.

Most of the time, effective communication between friends relies on finding the right questions to ask your friends.

We've compiled a list of our favorite questions to ask a friend – so the next time you're at a loss for words in a relationship that means a lot to you, we've got your back.


7 Best Questions To Ask Friends

This list of best questions to ask friends all have one thing in common: They reveal more intimate information about both you and your friend, helping to build a deeper friendship between you.

Here are the 7 best questions to ask friends:

1. What emotions are you experiencing over the past few days?

Sometimes you can tell what emotions are most prevalent for someone by the lines on their face. This question is great to ask your friends because it helps them focus on where they're at right now.

2. Have you ever been embarrassed in front of many people before?

Some peoples' brains are hard-wired for embarrassment. Is your friend easily embarrassed, or rather shameless?

3. What one quality about yourself are you most proud of?

Help support your friend's confidence with questions that make them consider what is most positive about them.

4. Do you have anyone who has a significant influence on you?

Who a person spends time with makes a big difference in their life, and this question asks your friend to consider that.

5. Despite all the ups and downs this year, what has been the most memorable moment for you?

It's important as a friend to remind your friends of what is going well in their lives, not just what is difficult.

6. If a genie can grant you anything you want to change about yourself, what would it be?

A desire for change has created the whole self-help industry, and knowing what your friend wants to change helps you know them better.

5 Conversation Starters To Ask Your Friends

Are you struggling to get your talks with a friend off on the right foot? Or maybe just looking for a quick question to ask over text so you can meet in person to talk about it later? Look no further than our selection of some of our favorite conversation starters.

Here are 5 conversation starters to ask friends:

8. If you could do anything for the rest of your life, what would that be?

Money aside, this question is perfect for starting a conversation because it can take literally any direction, and be expanded upon indefinitely.

9. If you had the option of adopting a baby fox or baby koala, which one would you choose?

Because sometimes the best way to start a conversation is with a silly question that will catch your friend totally off-guard.

10. If you had to be on a reality TV show, which one would you choose?

Reality TV is a strange new world... And if you can't come up with an answer, maybe it's time to make up your own show!

11. If you could live anywhere in the world for a year, where would it be?

Wanderlust is the German word for an intense desire to travel. Do you and your friend share in this desire?

12. What was the most memorable toy you played with from when you were little?

Childhood memories are a powerful way to connect on a more personal level.

5 Get to Know You Questions To Ask Your Friends

Maintaining friendships as an adult is fundamentally different from how friendships worked as children. By putting in the effort to consistently learn more about your friends, you can avoid a lot of common pitfalls of developing friendships as an adult. Try out this handful of get to know you questions to ask your friends!

Here are 5 get to know you questions to ask friends:

13. Have you ever had an accident where you got your bones broken?

Behind every broken bone is a story waiting to be told. Do you have any broken bone stories to share, too?

14. When you were little, what did you want to be?

Childhood dreams live inside of every adult, just waiting to be nurtured and set free.

15. What are the things you wanted to achieve when you reach 50?

Motivational speakers have built a whole industry out of helping people to achieve their goals and aspirations, making it a perfect question to ask just about anyone.

16. What are your fears about getting older?

Getting older is a part of life for everyone, and having honest discussions about our fears is a powerful form of catharsis.

17. What is one thing you are deeply proud of in your life?

Having a healthy sense of pride can be deeply fulfilling, and learning about what a person is proud of is a great way to get to know them.

5 Questions To Ask Your Best Friend

Male friendships can be somewhat confusing to anyone outside of them, but deeply bonded at a fundamental level. Even when you've know each other forever, there are always more questions to ask your best friend that you can learn. Maybe it's been a while since you and your best bud have had a good, long talk; that's what these questions are here to encourage.

Here are 5 questions to ask your best friend:

18. Is there anything I can do that will make your heart rest easier? Your life run smoother?

This question gets to the nitty-gritty of best friendship: How can we help make each others' lives better?

19. Who are your top three real life heroes?

The people we aspire to be can be a powerful motivator for our actions in the here and now; reminding a friend of these things can be a great way to help them stay on track in life.

20. What do you want more than anything else in life?

Our desires shape us as humans. What is most important in your best friend's life? How can you help them achieve that thing?

21. When was the last time you completely lost yourself in something?

Every once in a while, something seems to grab ahold of us and take us in a new direction in life. Sharing these things with our best friends makes them more real, more tangible.

5 Fun Questions To Ask Your Friends

When you're out at a party or other social event with a group, it's a great idea to have a handful of fun questions to ask to keep the conversation moving smoothly and naturally. Keep your group of friends on their toes with these fun, interesting questions.

Here are 5 fun questions to ask friends:

23. If you could change your first name what would you change it to?

Have you ever noticed that some people just don't feel like the name they go by? And who gets to choose those names, anyway?

26. What would you like to eat for your last meal?

There's a whole website dedicated to famous last meals – how does your friend's idea stack up?

27. If you had to make an alias, what would your name be?

A classic formula is to use the name of your first pet, followed by the street you grew up on.

8 Funny Questions To Ask Your Friends

Humor is important to seemingly everything, from health to work to relationships. It's equally important in friendships, too! And having a great selection of funny questions to ask your friends can make it that much easier to inject all-important humor into your conversations.

Here are 8 funny questions to ask friends:

28. How old is the most expired item in your fridge?

Everybody has at least one thing in their fridge that they just haven't made the effort to get rid of; this commonality can be the basis of great humor.

29. What food will you absolutely not, under any circumstances, eat?

After your friend reveals their most hated food, it can be funny and challenging to see just how true they'll stick to this conviction by offering them that food item in many different ways.

30. What’s the weirdest thing you’ve ever done on a date?

There are all sorts of reasons for people to act weird on dates, but hearing your friends' weird stories is much funnier than listening to a stranger.

31. What was the last lie you told/worst lie you’ve ever told?

You can be more honest around friends, and really a lot of times lies can be funny outside of their original context.

32. What was the real last time you washed your jeans?

Emphasis on real for this one! Are you guilty of keeping unwashed jeans, too?

 33. What animal most closely resembles your eating style?

You can up the funny factor on this one by asking your friend to imitate the animal they choose.

 34. Have you ever sent someone a text you didn't mean to?

And then, the natural follow-up: What happened? What was the text? Who was it meant for?

8 Would You Rather Questions To Ask Your Friends

Would You Rather is a classic game that leverages the human psyche's difficulty in making choices. These Would You Rather questions to ask your friends will introduce this minor pain, all for the reward of the pleasure of a conversation and a laugh with friends.

Here are 8 would you rather questions to ask friends:

36. Would you rather get lunch with Gillian Flynn or J.K. Rowling?

This question is perfect if you have a friend who's a real bookworm.

37. Would you rather not shower for a month, or eat the same meal everyday for a month?

A tough choice, indeed! Smelly, or bored?

38. Would you rather eat dog food or cat food?

This one's almost not fair. Make sure to specify that they can't ever choose "neither"!

 39. Would you rather be bald or covered from head to toe in hair?

Forcing the choice between Wolfman and Captain Picard can make for a humorous response from your friend.

40. Would you rather be an ugly genius or good looking and stupid?

What is more important to your friend – looks, or smarts?

41. Would you rather go to space or to the bottom of the ocean?

Both are unexplored frontiers for humankind. Where does your friend's curiosity lie?

42. Would you rather live in a country that was too hot all the time or freezing cold all the time?

There's no doubt that people have a definite preference for certain types of weather, but which side does your friend fall on?

43. Would you rather be poor with great friends or rich with none?

Oftentimes, "Would You Rather" questions can get to the heart of what is most important to someone.

8 Truth or Dare Questions To Ask  Your Friends

Maybe no other party game has survived as long as "Truth or Dare", with a group of people taking turns asking each other questions (truth) or giving directions (dare). Forewarned is forearmed, so if you're going into a party where the game might be played, it's best to have some great truth or dare questions, like the following.

Here are 8 truth or dare questions to ask friends:

44. Describe what your crush looks like using 1 word at a time.

Or make this dare even better, by giving specific details that they have to share (eyes, body, clothes, etc.)

45. Name one thing you would change about each person in this room.

The truth hurts may not be entirely true, but it definitely can sting a little bit; dare your friend to be honest with this one.

46. If your friend asked you to lie for her and you knew you would get in trouble, would you do it?

Just how good of a friend is your friend, anyway?

48. What's the longest you've gone without a shower?

Asking "truth" questions that make people reveal embarrassing details (like this one) can be delightfully excruciating for the person answering.

49. Go around the room and say one positive and one negative thing about each person.

This dare is especially powerful if the person you're telling to do it is usually shy and quiet.

7 Deep Questions To Ask Your Friends

Building deeper relationships in your life is an ongoing process of finding the right deep questions to ask, making the time and space necessary to have those conversations, and then following through – especially when those talks can seem difficult. While the process of making deeper friendships can be tricky, we're confident that having a great selection of deep questions to ask will get you well on your way towards long-lasting, solid friendships.

Here are 7 deep questions to ask friends:

52. Do you think you consider yourself brave during challenging times?

Thomas Paine once said "The real man smiles in trouble, gathers strength from distress, and grows brave by reflection." Has your friend taken the time for this reflection?

54. What is one thing you regret having done or not done in your life?

Regrets can weigh heavily on anyone, but having someone to talk about them with can ease the burden.

55. Are you proud of what you’re doing with your heart and time right now?

This question gets right to the core matters of life: Is your friend content with how they're living life, right now?

56. When was the last time you cried while being alone?

Most men get a bad rap for how they deal with crying, but talking about when and why it happened can be a big help in understanding your friendship that much better.

58. Have you ever questioned your beliefs and why?

The great philosopher Plato said that "The unexamined life is not worth living." If this is true, how much time has your friend spent in examination of their beliefs about life? What has this led them to?

6 Random Questions to Ask Friends

Have you ever gotten to the end of a conversation and didn't know what to say next. Then you need some random questions up your sleeve.

Here are 6 random questions to ask friends: 

59. What horror fiction character scares you the most?

Whether it is a book or a movie, those characters can really haunt your dreams.

60. What food do you crave more than any other?

We all have weird cravings. But who has the strangest?

61. Which holiday would you erase altogether from our calendars if given the opportunity?

With so many holidays on the calendar, there is bound to be one that they want to get rid of.

62. What word you heard the first time sounded intelligent without knowing the meaning?

Let them show off their intellect with this question.

63. What do you collect that no one knows about?

From rocks to baseball cards, everyone collects something. Let's just hope it is not something too weird.

64. What's the dumbest thing you've ever done on a dare?

We were all young once, but only a handful of us have really done something super stupid on a dare.

7 Never Have I Ever Questions to Ask Friends

Never have I ever questions are hilarious, especially when you play it with your friends. I mean, what's a couple of secrets amongst friends?

Here are 7 never have I ever questions to ask friends: 

65. Never have I ever Illegally taken something across the border.

Most people haven't smuggled something over the border, but those who have fantastic stories.

67. Never have I ever Gone to the bathroom and then not wash my hands.

Remember, when you ask this question, there is bound to be someone who does this. Just make sure you never shake their hand again.

68. Never have I ever blown my nose into anything other than tissue.

Hey, look, when you need to blow your nose, you need to blow your nose. But just not in the table cloth ok?

69. Never have I ever broken the law.

The more detail included in the answer, the better.

70. Never have I ever laughed so hard my beverage shot out of my nose.

Hopefully, it wasn't hot tea.

71. Never Have I Ever had a job that I absolutely despised.

If someone hasn't ever had a job they despised, they must be doing something right.

7 Weird Questions to Ask Friends

Questions are for people you don't really know. But weird questions are for the people that you know so well, that you really have to think outside of the box.

Here are 7 weird questions to ask friends:

74. Do you have an old shirt you cannot let go of?

Everyone has that one piece of clothing they would never get rid of.

75. What keeps you busy during weekends?

From baseball to volunteering, you'll be amazed by people's answers.

76. Do you think that life been hard on you so far?

Everyone has their ups and downs. But some have had it worse than others.

77. What is the highest-pressure situation you have ever been in and how did you handle it?

Knowing how someone deals with stress can tell you a lot about a person.

78. What characteristics make a person “successful?”

Success changes from person to person. By knowing everyone's own definition of success, you learn more about the person.

6 Ice Breaker Questions to Ask Friends

When you are meeting new people, it can be difficult to think of ways to start a conversation. But with a couple of ice breaker questions up your sleeve, you will be deep in conversation in no time.

Here are 6 ice breaker questions to ask friends: 

79. Do you believe in paranormal or extraterrestrial events?

It's hard to not believe in ghosts when the filter on your phone puts ears on a face that isn't there.

80. What do you think is the absolute worst song in the world?

This is probably one of the best questions you can ask. But beware. It can get heated.

81. What is your culinary specialty? How long did you learn it?

Everyone has that one thing that they can cook. For some, it's a Thanksgiving dinner; for others, it's grilled cheese.


8 Interesting Questions to Ask Friends

Want to really know more about someone? Then why not ask some interesting questions? From the weird to the downright strange, you are sure to find out something new.

Here are 8 interesting questions to ask friends: 

85. What do a lot of parents do that screws up their kid/s?

As former kids, I'm pretty sure that your friends will have an opinion on this.

86. Do you believe in life having a purpose, do you have one?

There is something really inspiring when you meet someone who has a purpose. It can really get you motivated.

87. Do you have a secret hunch about how you will die?

It's funny how everyone has some idea about how they're going to die, but how true can they be?

90. If you could learn any language fluently, what would it be?

Did you know that your friend wanted to learn Korean? Well, now, you do!

92. What was the thing you mostly got grounded for?

We all made stupid mistakes as kids, and asking this question will help you find out exactly how stupid.

6 Personal Questions to Ask Friends

You should really only ask people that you know really well personal questions. Like I mean, really well. You never know what you might learn.

Here are 6 personal questions to ask friends: 

93. Are you good at forgiving people, or do you hold grudges?

Some people are really good at forgiving each other while others just can't.

94. Are there any diseases that run in your family?

This question should be reserved for people that you know really well.

95. Are you close to your family or not?

While this question is a difficult one to answer, it's a great one to ask.

96. What’s the strangest dream you’ve had lately?

Dreams are weird, but they fade. Strange dreams, however, stay with you forever.

97. As a kid, were you ever frighted of a monster under the bed or in the cupboard?

You don't have to be a kid to be afraid of a monster under your bed. They still live there. Don't they?

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

This question is great when you want some holiday ideas.

Downloadable and Printable List of Questions To Ask Friends

Here is a downloadable and printable list of questions to ask friends (right click the image and select Save Image As...):

More Great Questions To Ask

Didn't find the specific topic you were looking for? Or maybe just want a few more great questions to ask? We've got you covered:

  1. General conversation topics are a great place to start thinking about how to talk to people.
  2. Need something specifically for your bros? Try our questions to ask a guy.
  3. If you're trying to develop a bond with a guy, look no further than our questions to ask a guy to get to know him.

How to Pick the Best Questions To Ask Your Friends

Wondering how to choose the best questions to ask your friends?

Here is how to pick questions to ask your friends:

1. Assess your relationship

Is this a deep friendship, or is it just getting started? Deeper friends ask deeper questions.

2. Observe the environment

More personal questions should be reserved for smaller groups, while general questions are great for parties and get-togethers.

3. Go with your gut

If you're really not sure how to ask a question, let your instinct guide you.

In Conclusion

Well, there you have it: Some of our favorite, most powerful questions to ask friends. Whether you were looking for funny, generic questions to ask your friends, or a more specific and deep question to ask a friend to know them better, it's all covered in the above categories. Now get out there and start making conversation, you're ready!***

About The Author


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, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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