A Whole Bunch of Questions!

Random Questions to Ask Your Friends!

• What do you like to do for fun?

• What’s the best birthday party you’ve ever had?

• Where is your favorite place you’ve ever visited?

• What’s one of your favorite bands?

• What is the cutest animal you’ve ever seen in person?

• How would you describe your style?

• If your wardrobe could only be one color, what would it be? 

• What was the first concert you ever went to?

• What is the best book you’ve ever read?

• What’s your favorite movie of all time? 

• What’s the stupidest movie or TV show you’ve ever seen?

• If you could only have one food for the rest of your life, what would you choose?

• What are your biggest pet peeves?

• Are you more into brains or looks?

• Do you celebrate any holidays? What’s your favorite?

• What’s your guilty pleasure? 

• Which meal is your favorite: breakfast, lunch, or dinner?

• What do you do when you want to chill out after a long day?

• How would you spend your ideal weekend?

• Do you listen to podcasts, or mostly just music? What’s your favorite podcast?

• Do you prefer to go to the movies or watch movies at home?

• What was your favorite TV show growing up?

• What’s your favorite TV show now?

• How would you spend your birthday if money was no object? 

• What’s your favorite season? What do you love most about it?

• Do you prefer camping or going to the beach? 

• Which phone app do you think you use the most?

• Would you instead cook, order delivery, or go out to eat? 

• How do you drink your coffee?

• If you could have any animal as a pet, what would you choose? 

• Do you enjoy being alone? How do you spend your alone time?  

• What is your biggest pet peeve?

• Are you more of an extrovert or introvert? 

• How would your closest friends describe you? 

• When you’re in a bad mood, is there something or someone that can instantly make it better? Who or what?

• What is the best gift you’ve ever received? 

• What is your favorite part of your daily routine? 

Yes or No Questions to Ask Your Friends

• Have you ever kept a journal? 

• Do you have a best friend?

• Do you pay attention to the news?

• Have you ever gotten a speeding ticket? 

• Do you live alone?

• Do you have any kids?

• Do you like your job?

• Did you ever go to college?

• Have you ever been on TV?

• Do you believe in ghosts?

• Do you like cilantro? 

• Do you ever talk to yourself in your head?

• Do you sing in the shower?

• Have you ever had deja vu? 

• Do you believe in aliens?

• Do you like chocolate?

• Do you own bitcoin? 
  

Questions to Ask People About Their Job

• What do you enjoy most about your career?

• What was your greatest accomplishment in the past year?

• What motivates you to work hard at what you do? 

• How long have you been doing this job? 

• What was your first job? Did you enjoy it?

• How do you define success?

• What’s your least favorite thing about your job? 

• Have you ever had “imposter syndrome”? What did you do about it? 

• Would you instead make a lot of money at a job you hate or make less money doing something you love? 

• Are there any exciting projects you’re currently working on?

• Do you prefer working remotely or in an office?

• What career did your parents try to get you to pursue?

• Is your career path the same as your college degree?

• What does the average week look like for you?

• Do you prefer a time-block schedule or a simple to-do list?

• What are your career aspirations?

• What is one job you’ve always wanted to try?

• Do you think your personality matches your current job?

• What was the worst interview you ever had?

• Where do you see yourself professionally in the next 5 or 10 years?

• When you were a kid, how did you answer the question, “what do you want to be when you grow up?”

• Did you ever expect yourself to end up in the job you have now?

• Do you consider your job fulfilling? Why or why not?

• Do you think it’s possible to have your passion and job be the same thing?

• What is the wisest business advice someone has ever given you?

• Who do you admire most in your professional circle?

• Who was the most influential mentor in your career so far? 

Questions to Ask Your Friends About Yourself

• How would you describe me in 3 words?

• What was the first thing you thought of me when we met?

• What’s the most annoying trait I have?

• Where do you see me in five years?

• What attracts you to people? 

• What is my favorite food?

• What job do you think I would be perfect for? 

• Where can you always find me?

• What is the most fun memory we’ve had during our friendship? 

• Do you know my middle name?

• Do you know about my birthday?

• What’s my favorite color? 

• If I called you in the middle of the night, would you pick me up?

Questions to Ask About Hobbies

• What are you passionate about outside of work?

• If you had unlimited free time, how would you spend it?

• Do you have any hobbies?

• How did you get into your hobby? 

• What lights you up about your hobbies?

• Do you collect anything?

• What’s your favorite sport?

• Have you ever been in a sports league? 

• Do you think hobbies are important? 

• Would you consider yourself a creative person?

• Have you ever tried a creative endeavor like painting, writing, or acting?

• Do you like to sing or dance?

• What hobbies did you try as a kid? Which ones did you love and which did you despise?

• What is your idea of a perfect vacation?

• What’s your favorite type of workout or exercise? 

• What is your favorite thing to learn about?

Funny and Weird Questions to Ask Your Friends

• Have you ever waved at someone thinking you know them, only to realize they are the wrong person? 

• What is a song you pretend you don’t like because it’s embarrassing to own it? 

• Have you ever tried to look cool in front of someone and failed?

• What’s the strangest thing you’ve seen someone do in public? 

• When was the last time you had a big fail moment? 

• What voice accent impersonations can you do (British, Australian, country, etc.)? 

• What’s your favorite corny joke?

• Have you ever tripped or fallen in front of a vast crowd?

• What is the weirdest fact you know?

• Do you have a unique talent? 

• What is the strangest joke someone has asked you? 

• If you could have one useless superpower, what would it be?

• If animals could talk, which would be the most sarcastic?

• What’s the most awkward first date you’ve ever been on? 

• What’s your favorite white elephant gift?

• Where is the worst smelling place you’ve ever been? 

• What is the most fruitless talent you have? 

• Why is it called lipstick if it doesn’t stick your lips together?

• What’s the silliest way you’ve accidentally injured yourself?

• What would be the worst bio for a dating app? 

Questions About Family

• Who is your closest family member?

• Do you have a best friend that you talk to daily?

• What kind of relationship do you have with your parents? 

• How much time do you usually spend with your family?

• Who in your family do you most enjoy being around, and why?

• Which family member cooks the best food?

• What’s the most challenging part about spending time away from your family?

• Do you have any siblings? Tell me about them?

• Are you close with your brother(s)/sister(s)? What drives you crazy about them?

• Do you ever wish you had more or fewer siblings?

• Who gives the best gifts in your family?

• Which holiday did you celebrate most with your family when growing up?

• What’s your favorite story your grandparents have told you?

• Have you ever looked into your family lineage? Do you know anything about your ancestry?

• What is your favorite childhood memory?

• What is the best piece of advice your grandparents or parents have ever given you?

• Were you a rebel or an obedient kid growing up? Did you hide things from your parents?

• How would you describe your family now?

• Does anyone in your family have a nickname for you?

• What’s your favorite tradition in your family?

• What will always bring your family together?

• Is anyone in your family a “character”? What makes them so unique?

• Who is the “black sheep” of your family?

• Do you think friends or family are more important?

• How do you deal with arguments in your family?

• What’s something your family doesn’t know about you?

• Do you look more like your mom or dad?

• Do you know how your parents met?

• What was your favorite story your family members told you as a kid?

• What was the most challenging part about growing up in your family?

• What are you most grateful for about your family?

• Who in your family makes you feel the safest?

• Is there a particular food your family always makes when they get together?

• What kind of music does your family listen to? 

• What was the house like that you grew up in? 

Questions About Values and Goals

• How do you hope people feel when they’re around you?

• What are the most important values that you have always stood by?

• How would you define a “good person”? 

• What are the most essential qualities you want in a friend?

• What life lessons did you have to learn the hard way?

• If you only had one of your five senses, which one would you choose?

• Have you ever volunteered?

• What are causes important to you? 

• Who do you admire the most and why?

• What is your life motto or mantra?

• What was your most proud accomplishment in the past year?

• If you could choose one thing that would make the world better, what would it be?

• Do you believe in giving people second chances?

• How can someone earn your trust?

• What has someone done to lose your trust?

• Do you believe in aliens or life on other planets?

• What do you think about manifestation? Have you ever tried it? 

• Do you have vivid dreams? 

• Do you think dreams have a deeper meaning?

• Where have you always dreamed of going?

• Do you believe you should do one thing every day that scares you?

• What does getting out of your comfort zone look like for you?

• How do you define beauty in a person or life?

• What is a boundary you have that you’ve always upheld?

• What boundary do you have a more challenging time reinforcing?

• What do you think holds people back the most from achieving their goals and dreams?

• When you want to give up on something, what keeps you moving forward?

• When was the last time you had a regret?

• Do you live by any particular words of wisdom?

• Is it easy or difficult for you to accept help from people?

• If money were no object, what would you devote your life to? 

• Have you ever wanted to start a business? What kind would it be and why?

• If you could live forever, would you want to? Why?

• If you could time travel, what period would you go to?

• If you could go back in history and spend a day with one famous person, would it be?

• Do you have a vision board? If so, what is currently on it?

• A genie in a bottle randomly gives you three wishes– what are they?

• If you could live anywhere in the world, where would you choose? Why?

• If you found out today was your last day on Earth, how would you spend it?

• If you find yourself stranded on a deserted island, what three things would you want to have with you? 

• What is your number one goal for the coming year?

Deep Questions to Ask Your Friends

• How would you title this chapter of your life? 

• If you only had one month left to live, how would you spend it? 

• What is the best advice someone has ever given you? 

• What makes you feel alive?

• Do you typically follow your heart or your head?

• What are you most grateful for in your life? 

• If you could go back and change one thing about your past, what would it be? 

• Which is more critical – beauty, power, or money? 

• What’s your biggest fear?

• What makes you feel unstoppable?

• What is your biggest regret?

• Do you think people are mostly good or mostly evil? Why? 

• Where do you go when you need fresh inspiration?

• What’s your philosophy on life?

• Do you like diving into the deep end or easing your way into the water? (literally or figuratively)?

• What life-changing events have you experienced? 

• What’s one thing you would change about yourself? 

• Have you ever had a moment of deja vu? 

• What legacy do you want to leave on Earth once you’re gone? 

• What gives you hope?