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Questions to Ask Your Friends

Looking for questions to ask your friend to get to know them better? These conversation prompts are a great way to investigate who your friends are. What they stand for. And what they think about the future. Let’s jump in!

Disclaimer: If you’re feeling lonely and are struggling to find the right information available to you on this website, please seek the help of a licensed therapist or counselor who can help you to address what might be troubling you. For a good resource, visit the Mental Health America’s list.

Questions to ask your friends
Questions to ask your friends

My experience asking relationship-building questions to make friends…

Here’s the thing… I had problems making friends when I was growing up. I’ll admit it! The ability to break out of my comfort zone gave me the confidence to connect with others in a more meaningful way. The only thing that gave me that confidence was questions like these… It sounds corny!

But it works… Here are a few of my BEST tips for you.

  • Remember a few that you like – Keep a couple of your favorite questions in mind. Try to remember a few for when the moment strikes you.
  • Don’t forget these as a tool – Whenever there’s a dull moment, whether you’re with a spouse or family… pull out a few of these questions.
  • Don’t take it too seriously – Especially when it comes to spouses or those you might be romantically interested in. This isn’t a time to start digging! Have fun, make it silly, and don’t take it all too seriously.

Best questions to ask your friends

What would you buy if you had a billion dollars?

What are some songs that always get you singing along?

What brought your parents together?

What was your biggest kitchen blunder?

What was the wildest wager you ever placed?

Do you consider love to be blind?

With whom would you like to exchange lives?

What would you choose to steal if you had the chance?

If you were the owner of a five-star restaurant, what kind of food would you give your patrons?

Which season most closely matches your personality?

What do you think of pink flamingos or garden gnomes?

If you had the chance to educate every female on the earth about males, what would you tell them?

Which flight did you take that was the longest you’ve ever taken?

If you were a vegetable, which one would you be?

Would you mind telling me a tale?

Want to make the world a better place?

Which of your present habits would you like to break?

Do you have any particular meaning for Christmas?

What sport from the Paralympics is your favorite?

Friendship Tip: Friendships are good for your health. According to the Harvard Study of Adult Development, there is a strong connection between personal relationships and longer lifespans.

Related: Dirty questions for friends

Questions to ask your friends
Questions to ask your friends

Fun questions to ask your friends

What is the silliest thing you have ever been duped into doing or thinking?

What is a fact that no one disagrees with you on?

What musical instrument makes the funniest noise?

If you had to leave the nation, where would you move to?

Do you consider what others have to say?

Who would you like to meet if you could meet anyone alive today?

What kind of cheese is best for you?

What was the biggest gamble you ever made?

Questions to ask your friends
Questions to ask your friends

Weird questions to ask your friends

Are you more of a get-up-and-go explorer or a relax-by-the-pool kind while you’re on vacation?

Do you regard yourself as spiritual or religious?

What major in college are you considering, and why?

Who would you select if you could only listen to one musician or band for the rest of your life?

What meal do you always make when you have to cook dinner?

Do you believe in superstitions?

Which board game is your favorite to play?

Who plays the finest villain in films?

Did you have a childhood imaginary friend?

What three words, if any, would you use, to sum up who you are? What adjectives would your friends use to characterize you, in their opinion?

What was your favorite snack as a kid?

What day of the week is your favorite?

Which month is your favorite?

Which classmate was your favorite?

Which continent have you visited already?

Which architectural design do you believe best suits you in homes?

Have you ever left a movie theatre before it was finished?

Which film you’ve seen a million times is your all-time favorite?

When you were a child, what did you want to be when you grew up?

Where would you go if money were no object and you could go anywhere in the world?

If you were to win the lotto, what would you do?

Questions to ask your friends
Questions to ask your friends

Freaky questions to ask your friends

What was your most recent lie?

Who was your first love interest?

Which of your past compliments stands out as the best?

What do you think is the nicest thing about your body?

What are the top three sources of your stress?

What are your top three stress-reduction strategies?

How recently have you been envious, and why?

Do you support monogamy?

What would your ideal marriage proposal entail if you made the decision to get married someday?

What style would your ideal house have?

When was the last time you had a creative spark?

What brought your parents together?

Who was your favorite professor?

What names for children do you prefer?

What did you envision the night before?

John Tholen, PhD
John Tholen, PhD

Why are friends important? John F. Tholen, P.h.D., describes good friendships should come above careers, accomplishments, fame, and wealth.

Random questions to ask your friends

What is your all-time favorite way to sleep?

Which of your injuries was the most foolish?

What are your top three favorite scents?

What new sport will emerge next?

Which board game is your favorite?

If you could only use one word for the rest of your life, which one would it be?

Would you prefer brains to beauty?

What was your embarrassing experience in elementary school?

Would you prefer to stay home or go out on a Friday night?

Have you ever thrown a lavish party for someone?

Deep questions to ask your friends

If you could alter anything about yourself, what would it be?

What spurs you to exert yourself?

Which mode of public transit do you favor? (Avial, a boat, a train, a bus, a vehicle, etc.)

What recent action did you take that was the most impulsive?

Which two radio stations do you often listen to when driving?

Which of the following tasks, cleaning, cooking, or yard maintenance, would you pay someone to assist you with?

Why do you think a vacation in Russia or Florida would be preferable?

What do you find most enjoyable about your job?

Which location, if any, would you like to call home?

Name a historical figure that inspires you to do better in your life?

Are you more of an extrovert or an introvert?

What do you most appreciate?

Which parent do you identify with more, and why?

What do you think of Tinder or online dating in general?

What do you have planned for this year?

What would you say about your closest friend?

How do you feel about best friends who are the other sex?

What motivates you to feel successful?

What do you think about telling your lover your password?

What stage of your life was the best?

If your partner was given a fatal illness diagnosis, would you still love them?

What aspects of your parents do you admire?

Interesting questions to ask your friends

Which emoji do you use the most?

Who would you like to sit next to you if you could sit on a bench in the middle of a gorgeous forest, and why?

What kind of fruit, if any, would you be?

What will you do with the time you have left when the doctor tells you that you only have 24 hours to live?

Have you ever removed something from your possession and forgotten to put it back?

Do you ever have faith in brave acts?

On a scale of 1 to 10, what level of agony have you ever felt was the worst?

What comes to mind when you see a homeless human?

How do you unwind after a demanding day?

Who serves as your example?

Which famous person would you most like to meet?

What is anything that you have never been skilled at?

What about a lady do you usually find most striking?

Which of your childhood memories do you prefer?

What accomplishment do you feel most proud of?

Truth or dare questions to ask your friends


Have you had a secret talent?

Who was your first crush on a celebrity?

What do you think about polyamory?

Which of your past personal encounters was the worst?

Have you ever used exam cheating tactics?

When were you ever the most inebriated?

Do you have a criminal record?

What has been your most humiliating moment?

What is your biggest weakness?

What was your worst error in judgment?

What was the grossest thing you ever did?

In this room, who would you like to kiss?

What has someone ever done to you that you feel was the worst thing that has ever happened to you?

Have you ever encountered the law?

Name one of your bad habits.

The worst thing you’ve ever said to someone was what?

What’s the weirdest thing you’ve done in the shower?

Hard questions to ask your friends

Whom would you like to spend time with if you were marooned on an island?

What one thing would you alter if you could go back in time?

Who would you choose as your four dinner companions, alive or otherwise?

What number of pillows do you use to sleep?

How long have you gone without sleep, and why?

What is the tallest structure you have climbed to the top of?

What movie did you see recently? How did you feel?

When you were younger, what did you want to be?

In five years, where do you see yourself?

Do you think that second chances exist?

What has been your life’s biggest error to yet, and what have you learned from it?

Where in the globe is your favorite destination?

What have you learned from your prior relationships?

What guidelines do you live by?

Which five movies rank as your favorites?

If your parents disapproved of your spouse, what would you do?

Easy questions to ask your friends

Are you a spiritual person?

Which family member do you love the most?

Do you have a hidden talent?

What’s your most annoying trait?

What’s something that’s on your bucket list?

What’s your dream job?

Who was your last romantic partner?

Do you have any clever pick-up phrases?

Do you have a recent action you regret?

What board game is your least favorite?

What will be most important to you when you are 80?

Ever been caught looking at someone of the other gender?

Do you want to become famous one day?

Which five fast-food places top your list?

Which smartphone manufacturer do you detest the most?

Have you ever had to elude law enforcement?

What rule would you wish to enact that everyone must adhere to exactly?

In a movie, would you prefer playing the villain or the hero?

Do you value beauty or intellect more?

When do you consider someone to be prepared for marriage?

Is what you’re doing today what you always envisioned doing when you were younger?

Have you ever suffered the loss of a loved one?

Do you like to be left alone or have someone cheer you up when you’re in a foul mood?

Dumb questions to ask ’em

—Dumb questions to ask your friends

Have you ever eaten something you picked up from the floor after dropping it?

What indoor activity do you prefer?

Which outdoor activity is your favorite?

Do you quickly become bored?

Who would you pick as your one imaginary friend if you could only have one?

If you could live at any age for the remainder of your life, which age would you prefer and why?

If you could teleport from one area to another, where would you go?

Have you ever eaten something that you picked up from the floor after dropping it?

What indoor activity do you prefer?

Which outdoor activity is your favorite?

Do you quickly become bored?

What’s your favorite holiday?

What one superpower do you wish you had?

What advice would you give your younger self?

What’s the weirdest gift you’ve ever got?

Who would you pick as your one imaginary buddy, if you could only have one?

If you could live at any age for the remainder of your life, which age would you prefer and why?

Where would you go if you could teleport from one area to another?

Do you avoid being around machines?

Personal questions to ask them

—Personal questions to ask your friends

When you’re depressed or unhappy, how do you prefer to be consoled?

What is your most treasured memory?

Who caused you to weep most recently, and why?

Where do you envision yourself in five years? Ten? Fifteen?

When have you been most proud of yourself?

At what point did you feel most challenged?

Are you a victim of bullying?

Do you regret anything? What are they if so?

Which member of your family do you get along with the best?

What is one thing about you that most people don’t know?

What do you suppose occurs when we pass away?

Do you intend to have children someday? The number?

What is your earliest recollection from childhood?

What one thing about yourself would you alter if you could?

Do you think there are soul mates?

What keeps you up at night when you can’t sleep?

What has been the hardest farewell you have experienced thus far?

Which of your past dates was the worst?

What talent do you aspire to have, or are you currently developing?

What’s the most embarrassing moment to ever happen to you?

Who are your best friends, and why?

What’s your biggest pet peeve?

What’s your go-to dance move?

What does the perfect vacation look like to you?

What’s your favorite food?

What’s your favorite subject in school?

What’s the best quality to have in a friend?

What’s your favorite season?

What’s your favorite movie of all time?

What did your past relationship teach you about yourself?

What’s your biggest fear?

What’s your favorite childhood memory?

What’s the funniest joke you’ve ever heard?

Funny questions to ask

Funny questions to ask your friends

What will people feel nostalgic for in 40 years?

What unspoken guidelines govern your workplace?

Do you think pineapple should be used on pizza?

What scene in a children’s movie left you permanently scarred?

What type of covert organization would you wish to find?

Which animal would be the rudest if it could talk?

Over or under the toilet paper?

What kind of cheese is best?

What was the oddest place you’ve ever urinated or pooped?

What was the funniest inside joke you ever participated in?

How would you sum up the internet in one sentence?

What is the number of hens needed to kill an elephant?

Which outfit has ever made you feel the worst?

What is the most bizarre thing a visitor has ever done at your home?

What fabled being, if real, would make the world better?

What inanimate thing would you most like to see disappear from the world?

What is the strangest thing you have ever witnessed at a stranger’s home?

What would be the worst possible name to give a child?

What would be the worst thing the government could make illegal?

What pet names do you have for your clients or coworkers?

What would peanut butter be named if it weren’t called peanut butter?

What movie would benefit immensely from a musical adaptation?

What is the most hilarious business or corporate blunder you have heard of?

If you perform two completely typical activities back-to-back, which ones turn out to be incredibly strange?

What could you possibly purchase that would make the cashier the most uneasy?

What could you possibly say to a stranger you are passing on the street that would be the creepiest?

What have you recently discovered that you are ashamed you weren’t aware of earlier?

What are some entertaining and intriguing alternatives to conflict that nations may use to settle their disputes?


Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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