80 Interesting Questions to Ask People in Any Situation


Have you been out at a happy hour with co-workers lately and had to answer the same mundane questions about that project you’re all working on? What about stuck at a dinner at a family reunion, asking your aunt for the tenth time about her college days? Or on a first date, powering through the typical first date questions — “Where’d you go to college?” “What do you do for a living?”

If you’ve answered yes to any of the above questions, you know how frustrating and boring it can be to ask and answer the same questions over and over again. There’s nothing worse than having a boring, stifling conversation… just as there’s nothing better than truly getting to know someone and learning something unique about them.

In this article, I’ll help you revamp your small talk by giving you the 80 most interesting questions to ask people everywhere from a first date to a happy hour with coworkers.


The 20 Best Questions to Ask on a First Date

Ahh, first dates! Nothing can make or break a first date like conversation. These 20 funny questions to ask people will open up the channels of communication between you and your date and ensure that, however the date goes, it’ll certainly be memorable.

  1. Who inspires you? Who do you aspire to be like?
  2. Shark diving, bungee jumping, or skydiving?
  3. What’s your favorite cheesy pick-up line? Have you ever used it in real life?
  4. What’s your favorite Disney movie?
  5. What is the weirdest scar you have and how did you get it?
  6. Where did you and your best friend meet?
  7. Which of your accomplishments are you most proud of?
  8. What’s the weirdest Wikipedia rabbit hole you’ve stumbled down?
  9. Tell me about the best vacation you’ve ever taken.
  10. What’s your favorite physical attribute about yourself?
  11. Friday night – would you rather stay in or go out?
  12. Do you believe in ghosts?
  13. What piece of art (book, music, movie, etc.) most influenced the person you are today?
  14. Which would be harder for you to give up: coffee or alcohol?
  15. What’s the single best piece of advice you ever received?
  16. Who’s your best friend, and what do you love about him or her?
  17. What’s the greatest risk you’ve ever taken?
  18. If you had 24 hours to do whatever you wanted in this city, what would you do?
  19. What do you like about where you work?
  20. What hobby have you always wanted to develop?




The 20 Best Questions to Ask Friends You’ve Known Forever

We all have those friends we’ve known forever. You know, the ones that you make boxed macaroni and cheese with on Saturday nights for a Netflix binge. Even with those friends that we most love, conversations can get dull and repetitive. Here are some good questions to ask people for spicing up your conversations and getting to know your besties even better.

  1. Which house would you belong to in Hogwarts?
  2. What emotion do you experience the most?
  3. What was your first impression of me?
  4. If you were forced to open a bar, what would you name it?
  5. Would you rather be stuck in traffic for three hours, or never get Chipotle again?
  6. If you and I were to go to jail, what would it be for?
  7. If you could learn the date and time of your death, would you?
  8. What’s the most embarrassing thing you’ve ever done?
  9. Have you ever shoplifted? If yes, what did you take?
  10. What are the three things you would bring with you to a deserted island?
  11. What is one childhood superstition or fear you’ve never told anyone?
  12. What secret obsession do you have that I don’t know?
  13. If you could do anything for the rest of your life, what would it be?
  14. What makes you feel super loved?
  15. What do you lie most about?
  16. What’s the silliest thing that you’ve ever gotten upset about?
  17. If you had to spend $10,000 today, how would you spend it?
  18. What’s your favorite viral video?
  19. Who’s your least favorite celebrity?
  20. If you could re-do one day in your life, what would it be and why?




The 20 Best Questions to Get to Know Your Family Better

Have you ever taken the time to really get to know your parents? What about your grandparents? Aunts, uncles, cousins? I’m talking beyond their little pet peeves about putting the dishes away or folding your laundry. Consider asking your family members these questions about the next family get together. You’ll be surprised what you might learn.

  1. Did you have a nickname when you were growing up? If so, what was it and where did it come from?
  2. Where was your first home?
  3. Were you named after anyone?
  4. What were your earliest memories of your home?
  5. What was your favorite bedtime story as a kid?
  6. What was your high school experience like?
  7. What clothing fads did you love as a kid?
  8. Did you like school?
  9. Did you and your friends like to hang out anywhere special as a teenager?
  10. Do you remember your first date?
  11. Describe your wedding ceremony.
  12. What was an unusual thing your children did when they were very small?
  13. What historical moment stands out most in your memory?
  14. What did you find most difficult about growing up?
  15. Were your parents strict or lenient?
  16. Do you remember your grandparents or great-grandparents? What were they like?
  17. Have you ever been in a serious accident?
  18. Name a good friend you’ve known the longest. How many years have you been friends?
  19. If you could change one thing about your life, what would it be?
  20. If you had the opportunity to erase the last ___ years of your life and go back to age 18, would you do it? Why or why not?




The 20 Best Questions to Ask Your Co-Workers

Work. You spend hours there every week. But how well do you really know the people you’re there with every day? Fostering strong relationships with your co-workers is a great way to make your work experience more enjoyable. Try these funny questions to ask people the next time you’re gathered around the water cooler on break.

  1. What movie or book character do you most identify with?
  2. When are you happiest?
  3. What more are you wanting from your career right now?
  4. If you were to start a company from scratch, what would be its core values?
  5. What stresses you out the most at work?
  6. What would a perfect day look like for you?
  7. How would you spend a million dollars?
  8. If you could choose to remain an age forever, what age would you choose?
  9. What’s your favorite sport to watch?
  10. What was your most recent Netflix binge?
  11. What was the best thing that happened to you last weekend?
  12. If you could live anywhere in the world, where would it be?
  13. What’s the one skill you think everyone should have?
  14. Do you consider yourself artistic?
  15. Who was your most influential schoolteacher and why?
  16. What music would you recommend for me to listen to while I work?
  17. What would be the title of your autobiography?
  18. Do you have a favorite season?
  19. What’s the fanciest event you’ve ever been to?
  20. If you could go back to one historical event to witness it, what would it be and why?




The Bottom Line: Questions to Ask People to Get to Know Them

Conversations don’t have to be rote and boring! Use these 80 questions to spice up your next first date or family dinner. Use conversation as a way to better get to know the people in your life… and don’t forget to share about yourself, too!