Take Your Friendships To The Next Level By Asking These 202 Questions
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You'll never know your friends like the back of your hand, but you can definitely try. Whether you simply want to check in with your childhood bestie or forge a bond with a new work friend, asking the right questions can benefit any connection.
Of course, the convo needs to flow, not feel like an interrogation. You want to show your pal that you're interested in digging deeper into their personality because you like them, not because you want to put them in the hot seat.
One surprisingly easy way to jumpstart a bestie question sesh? Ask your friend questions about their past to get a better picture of where they came from, says Anna Akbari, PhD, a sociologist and former professor in the department of media, culture, and communication at New York University.
"We too often assume everyone has had the same experiences that shaped them that we have. [But] we all have different wounds that we carry with us," Akbari explains. "So the more you can understand that person's history, the more empathetic you can be for them."
Meet the Experts:
Anna Akbari, PhD, is a sociologist and former professor in the department of media, culture, and communication at New York University.
Danielle Bayard Jackson is a friendship coach and educator.
Marisa G. Franco, PhD, is a psychologist, friendship expert, and author of Platonic: How the Science of Attachment Can Help You Make–and Keep–Friends.
Another option? Ask your friend future-minded questions, which helps you understand what they're working toward, or what their idealized vision for their identity and their life looks like, Akbari says.
Alternatively, if you're catching up with an old pal, you can begin the convo by following up on previous chats. Try something as simple as, "Hey, whatever happened with that guy you went on a date with? What’s the deal?" says Danielle Bayard Jackson, a friendship coach and educator. Not only does it show you're interested in what's new with them, but it also shows that you were engaged and actively listening during your last conversation.
Asking your friends questions about themselves also encourages them to be vulnerable with you, and vice versa. It can be scary and intimidating to open up to another person (even someone you've known for years), but vulnerability uniquely benefits friendship. "The beauty of vulnerability is that it makes the other person feel more comfortable being vulnerable. And it's a great way to find commonality," says Marisa G. Franco, PhD, a psychologist and friendship expert. "We think [our vulnerabilities are] isolated, unique struggles, but often other people are able to say, 'Me too.' So it gives us a different kind of commonality outside of that which we met in." Take a look at your closest relationships, and you'll likely see the result of vulnerability working its magic.
Now that you know the kinds of questions to ask, it's time to get specific. These 202 juicy, fun, and deep questions to ask your friends will deepen any bestie bond:
Juicy Questions To Ask Friends
1. What’s the best advice a family member gave you growing up?
2. What’s the worst advice?
3. Who was your role model growing up?
4. What’s your proudest moment?
5. When have you felt the most challenged?
6. Who has been a big influence on you?
7. What’s the hardest lesson you’ve ever had to learn?
8. Who was your first kiss with, and did you enjoy it?
9. Who was your first love, and why did you love them?
10. What was your first heartbreak, and what happened?
11. What’s been your greatest accomplishment in life?
12. What was your experience in high school like?
13. How did your parents meet?
14. What did you think adulthood was like in your teens?
15. What’s something you’ve done that you didn’t expect to do at this age?
16. What’s the biggest lesson you’ve learned on your own?
17. What rating would you give your current job, on a scale of one to 10?
18. Who was the last person you talked to on the phone?
19. Tell me about the last date you went on. How did it go?
20. What’s one thing you would change about yourself right now?
21. Do you journal and, if so, what do you usually write about?
22. How would you rank your love languages?
23. If you got to live in another country for a year, where would you live?
24. Do you believe in love at first sight?
25. What are you most pessimistic about, and why?
26. What’s your favorite and least favorite genre of music?
27. What old trend did you participate in? Do you regret it now?
28. Do you believe in monogamy?
29. Do you believe in having a five-year plan?
30. If you could accomplish one thing in your life, what would it be?
Need even more question inspo? Watch the video below for questions that help you get to know people better...
31. What’s your biggest career goal?
32. Do you want to have kids someday? If so, how many?
33. What’s most important to you: work life or personal life?
34. Who do you aspire to be like?
35. If you had to move across the world for your dream job, would you?
36. How will you know you’ve “made it”?
37. What do you hope to achieve by 50, 60, 70, etc.?
38. What’s the first thing you do in the morning, and how does it impact the rest of your day?
39. When you make a resolution, do you stick to it?
41. Would you ever change careers?
42. Would you ever move out of state?
43. What qualities would you like in a future partner?
44. Which decade to come do you think will be your favorite, and why?
45. Would you ever return to school to get a degree?
Fun Questions To Ask Friends
1. What’s your favorite childhood memory?
2. How would you describe your childhood home?
3. Who was your first celebrity crush?
4. What was your first dream job, and is it still your dream job?
5. What’s your earliest memory?
6. Have you ever had a “life-changing” moment? If so, what was it?
7. What was the first concert you ever went to?
8. Who was your favorite childhood teacher?
9. What has been your favorite travel memory so far?
10. What was your best year so far, and why?
11. How were your summers spent when you were younger?
12. What was your best birthday and how did you celebrate?
13. Who is your celebrity crush right now?
14. What’s the best movie you’ve seen so far this year?
15. Who would you give an Oscar to this year, if you could award it to anyone?
16. What’s the best album you’ve listened to as of late?
17. Can you walk me through your entire day today, from start to finish?
18. What’s your most prized possession?
19. Do you have a sweet tooth, why or why not?
20. What’s your zodiac sign, and does it resonate with you?
21. What’s your go-to coffee order?
22. How would you improve your current living space right now, if you could?
23. Do you prefer savory or sweet? Explain.
24. What’s your favorite family recipe?
25. Have you been working out at all and, if so, what’s been your favorite activity?
26. What have you done for fun or leisure this week?
27. How would you describe your current style?
28. What’s your favorite podcast?
29. If you could pick any actor to play you in a movie, who would it be and why?
30. What’s your go-to Netflix recommendation?
31. If you could trade places with one celebrity for a day, who would it be and why?
32. What’s your favorite way to relax?
33. What’s the #1 thing on your bucket list?
34. If you could travel anywhere in the world (all expenses paid), where would you go?
35. What are you most looking forward to this year?
36. If you had unlimited money to start your own business, what would it be?
37. How do you plan to spend your retirement?
38. What’s one dish you really want to learn how to make?
39. What skill would you like to improve as you get older?
40. What hobby would you like to pick up again?
41. What does your dream proposal look like?
42. What concert do you wish you could go to?
Deep Questions To Ask Friends
1. Do you have any regrets? If so, what are they and why?
2. If you could change anything about your past, would you and what would it be?
3. What did you fear most growing up?
4. How have you dealt with past disappointments?
5. If you had a childhood pet and they passed away, how did you handle that?
6. Have you ever given up on a dream? What was it?
7. How has your relationship with your parents changed?
8. Have your values changed over time?
9. Would your younger self be proud of where you are in life now?
10. Have you ever been bullied?
11. What’s the biggest mistake you’ve ever made?
12. If you could change one thing about yourself, would you?
13. Have you ever had to break up with a friend? What was it like?
14. What did your first relationship teach you about love?
15. What’s the bravest thing you’ve ever done?
16. What’s the most hurtful thing you’ve experienced?
17. What have you learned about change?
18. What’s your biggest fear now?
19. How would you describe your current emotional state?
20. What are you grateful for today?
21. What’s your biggest insecurity?
22. What’s been occupying your mind the most lately?
23. What’s your current relationship with your siblings?
24. What’s something that reminds you of home?
25. What is something you need more of in your life right now?
26. What do you think would make your life better?
27. Do you believe we all have a purpose?
28. Do you believe in a higher power?
29. What qualities do you value most in a friend?
30. What value does friendship have in your life?
31. Do you worry about your future, or take things as they come?
32. How have your past experiences shaped your view of the future?
33. Are you afraid to grow older or excited?
34. How do you define success for yourself?
35. Are you happy where you’re living now, or do you plan to move?
36. When do you think you’ll know you’ve met “The One”?
37. What motivates you to go after your goals?
38. Does anything keep you up at night? If so, what?
39. Do you think your priorities will change over time or generally stay the same?
40. What would you be willing to give up to achieve your dreams?
41. What’s the best way to support you when you’re having a hard time?
42. What would you eat for your last meal?
43. If you had the opportunity to be immortal, would you take it?
44. What’s one cultural tradition you want to pass on to your kids?
45. What do you hope will change in society down the line?
46. What fear would you like to overcome?
47. In three words, how would you describe your future self?
48. If your home caught on fire, what would you try to save?
49. How do you think you’ll deal with loss down the line?
50. How would you like your relationship with your family to evolve?
51. Do you believe in soulmates?
Questions To Ask Friends About Yourself
1. What was your first impression of me when we met?
2. If you could steal one thing from my closet for yourself, what would it be?
3. Do you think we’ll always be friends?
4. What do you hope for our friendship as we grow older?
5. How can I be a better friend to you?
6. What’s your favorite quality of mine?
7. What’s the worst heartbreak I’ve ever experienced in your opinion?
8. When I’m sad, what makes me feel better?
9. What’s your all-time favorite memory of us?
10. What do you think my love language is?
11. Which pair of fictional best friends on TV best represent our friendship?
12. Who’s my celebrity crush?
13. Has there been anything I said or done in the past that really hurt you and I didn’t know?
14. Out of our entire friend group, who do you think I’m closest to?
15. Where do you hope to see me five years from now? Ten years?
16. Do you think I want kids? Why or why not?
17. Do you think I want to get married? Why or why not?
18. What’s a quirk of mine you find really funny?
19. What’s a personality trait you think I could work on?
20. What’s something you want to do together that we haven’t done yet?
21. What kind of energy do I give off: youngest sibling, middle child, oldest sibling, or only child?
22. What’s something that you know is on my bucket list?
23. If I could live anywhere in the world, where would it be and why?
24. If I were to move away, how do you think our friendship would change?
25. What two actors do you think should play us in a movie?
26. Which internet meme best describes my personality?
27. What would my dream home look like?
Random Questions To Ask Friends
1. What’s the weirdest thing you believed as a kid?
2. If you could relive any moment in your life, would you? Which one?
3. Do you have any weird habits that I don’t know about?
4. What was your favorite part of your day when you were a kid?
5. What was your favorite meal as a kid?
6. What song reminds you of your childhood?
7. What was your favorite subject in school?
8. Did you play any sports growing up?
9. What cultural traditions did you learn as a kid?
10. Who was your best friend as a child?
11. What was your least favorite book growing up?
12. Did you have an imaginary friend as a child?
13. What was your favorite snack as a child?
14. Do you consider yourself an introvert or extrovert?
15. Where is your favorite place to shop right now?
16. What book(s) are you currently reading?
17. What TV show are you in the middle of watching?
18. What’s your favorite item in your wardrobe right now?
19. What message would you put on a billboard right now, if you could?
20. What’s the coziest thing you own?
21. What are you hungry for right now?
22. What’s your favorite food right now? Favorite drink?
23. How do you prefer to cook your eggs (e.g., scrambled, over easy, sunny side up, etc.)?
24. If you could be any animal, which one would you be?
25. Do you believe in ghosts?
26. If you found out today was your last day on Earth, what would you do?
27. What would you do if you won the lottery?
28. What’s the most overrated holiday in your opinion?
29. Have you ever had a crush on a cartoon character, and, if so, who?
30. What’s the best prank you’ve ever pulled on someone?
31. If you were to invent a new word, what would it be and what would it mean?
32. Is there anything you’d wait in line for over 10 hours to see or get?
33. If you could only enjoy one condiment for the rest of your life, what would it be and why?
34. If you could legally marry an inanimate object, what would it be and why?
35. If you were a ghost, who would you haunt?
36. What’s your favorite dad joke?
37. How gullible do you consider yourself, on a scale of one to 10?
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