Have you ever found yourself in the promising position of making a new friend or perhaps even a love connection, only to be completely stumped when it comes to asking questions to learn more about this new person? It can be a challenge. Not everyone has the charisma and charm it takes to breeze through conversations – especially if you’re meeting someone for the first time.

People have layers and layers to their personality, formed through years of experiences, emotions, thoughts, and dreams. So if you’re going to dissect all of that, you need to come prepared with the right questions. Wondering what questions to ask to get to know someone better? Here are some top suggestions.

Questions About Family and Relationships

Questions About Family and Relationships

One of the easiest topics to talk about is family. Everyone has a family in some form or another – even pets count as family! So if you want to learn something new about a friend or acquaintance, this is an easy topic that’s sure to get the conversation going for hours. Use these interesting questions to ask someone to learn more about an acquaintance’s background and history, which should shed light on how they came to be the person they are today.

  1. How many siblings do you have?
  2. What’s your favorite childhood memory?
  3. Do you have any pets? What are they, their names, and how old are they?
  4. What was your favorite family vacation ever?
  5. Did you have a nickname growing up? How did that come to be?
  6. Did you have a neighborhood clique growing up? What did you do for fun?
  7. Which relative do you most resemble?
  8. What’s your favorite memory involving your parents?
  9. What personality traits did you inherit from your parents?
  10. What’s the story behind your name?
  11. How did you like to spend time with your siblings?
  12. What was your favorite dish that your dad or mom would cook for you?
  13. Do you have any special memories with your grandparents?
  14. Where did you live growing up?
  15. Did you have chores growing up? What were your chores and do you think it was a fair distribution among your siblings?
  16. What were your favorite songs growing up?
  17. What childhood fads (hairstyles, dress styles) did you try that you regret?
  18. Did you join any clubs, groups, or organizations as a kid?
  19. Could you name a childhood hero, fictional or otherwise? Why did you look up to them?
  20. What were your favorite cartoons growing up?
  21. Did you ever get to meet your great grandparents?
  22. Describe a typical family dinner. Is it noisy and rowdy or do you like to sit down and have quiet conversations?
  23. How do you celebrate the holidays in your family?
  24. Where did you meet your spouse or partner?
  25. How long have you been in a relationship with your partner?
  26. When and where did you get married?
  27. If there’s one thing you could change about the ceremony, what would it be and why?
  28. Do you have any kids? If not, do you plan to have kids and how many?
  29. How would you best describe your spouse or partner?
  30. How do you like to spend time with your partner?
  31. Where do you like to bring your family around for fun?
  32. What plans do you have for the summer?
  33. How would you best describe your kids?
  34. What’s one thing you would tell soon-to-be-parents to help them prepare for parenthood?
  35. What’s one thing you would tell soon-to-be-married couples to help them gear up for married life?

Questions About Education and Career

Questions About Education and Career

Work and school take up about 70% of our lives. So if you want to learn more about a person, it would be wise to ask questions about the things that take up most of their time. Questions about education and career give you a deeper look into a person’s interests and passions. Try using these interesting questions to ask someone to learn more about their work and school life.

  1. Where did/do you study? What did you take up in college?
  2. Are you interested in taking up post-graduate studies? In what field?
  3. What kind of job are you interested in taking once you finish school?
  4. What are your favorite subjects?
  5. Are you part of any special clubs or organizations at school?
  6. Are you a member of the student council? Is that something you would be interested in?
  7. What do you like to do for fun when you’re with your school friends?
  8. Who’s your favorite professor or teacher and why?
  9. Is there anyone or anything you draw inspiration from to do good in your studies?
  10. Would you ever consider teaching in your chosen field? Why or why not?
  11. What school projects did you do that you are most proud of?
  12. Are you an organized student or do you prefer doing things last minute?
  13. What subjects do you struggle most with and how do you try to cope with the challenge?
  14. Where do you work? Do you enjoy working for your current company?
  15. What position are you taking up? What duties and responsibilities does that entail?
  16. What skills do you use the most at work?
  17. What would you define as your shining moment at work?
  18. Do you have any plans to switch companies or employers? Why?
  19. Have you ever considered putting up your own business?
  20. What are you most passionate about in terms of your job?
  21. If there’s one thing you could change about your current work, what would it be and why?
  22. How do you get along with your coworkers? Who do you feel closest to in the office?
  23. Are you satisfied with your work life?
  24. Is this the kind of work that you thought or dreamed of having when you were a kid?
  25. If you could be the boss at your office for one day, how would you change the way things are done?
  26. If you could apply for any job right now with guaranteed acceptance, what job would it be and why?
  27. How do you expect your career to change within the next 10 years?
  28. What’s one thing you would tell college kids who have yet to step into the adult world?
  29. What bad habits do you think really get in the way of your productivity?
  30. What’s one thing you shouldn’t have done at work but did anyway?

Casual Questions About Entertainment and Pop Culture

Casual Questions About Entertainment and Pop Culture

We’re all big on Netflix and YouTube these days, and it’s impossible for people to not have some sort of guilty pleasure – whether it’s memes, music, movies, and more! These questions should help you get a better idea of what your new acquaintance or friend enjoys watching or listening to, so you can find something common and lay the groundwork for a strong friendship built on mutual interests.

  1. What’s one TV series that you just can’t get enough of?
  2. What your favorite movie of all time?
  3. What’s your favorite movie genre?
  4. Any good bands or music that you’ve listened to lately?
  5. What kind of music are you in to?
  6. What a show you like that you consider a guilty pleasure?
  7. What’s one movie that really isn’t that great, but you just can’t get enough of?
  8. Who’s your favorite fictional character?
  9. Have you read any good books? What’s one book that you love?
  10. Are you into documentaries or docu series shows? What’s your favorite?
  11. How much time do you spend on social media?
  12. What different social media platforms are most useful for you?\
  13. Do you prefer watching shows and movies, or listening to music?
  14. If you had to listen to one song on repeat for the rest of your life, what would it be and why?
  15. What’s one song that you can stand hearing?
  16. What’s one movie that you can never sit through and finish?
  17. If you could make your own movie or Tv show, what would it be about?
  18. If they were to make a movie about your life, who would act in your place?
  19. Who’s your favorite Hollywood actor or actress? What do you love about them?
  20. If you could trade singing voices with anyone in the world, who would it be and why?
  21. If you could live the celebrity life for a whole week, what would you do?
  22. Who would you consider your celebrity style inspiration?
  23. What’s your favorite Netflix original production?
  24. What’s one horror movie that really shook you up?
  25. Which one wins – smartphones or laptops?

Deep Questions to Ask Someone

Deep Questions to Ask Someone

Once you break through those first few meetings, you might start to discover the opportunity to ask you friend deeper questions to find out how they think and how they feel. These questions should help you learn more about the intricacies of your friend’s mind, their logical processes, and other deeper details that you might not have discovered with the casual questions listed above.

  1. If you were designated president for a week, what would you do and what things would you change about our current government?
  2. What advocacies are you most passionate about? What do you do in your day to day life to help reach the goals for your chosen advocacy?
  3. Do you think that a child’s upbringing has a lot to do with how they turn out as adults? Why or why not?
  4. How would you try to resolve global poverty if you were told to call the shots?
  5. Who do you think is responsible for climate change – individuals or governments?
  6. What do you think interests you that most other people don’t actually find interesting?
  7. Is it more important to be smart or wise?
  8. What’s one thing that other people say about you that always annoys you?
  9. What’s one thing that you thought would be bad but actually turned out to be pretty okay?
  10. What are some red flags that you look out for when meeting a new person?
  11. If you could talk to an intelligent alien life form, what would you tell them about the human race?
  12. What stigma or societal concept do you think we really need to get over on a global scale?
  13. What do you think is most important if you’re going on a date with someone for the first time?
  14. What’s the worst thing any other person has ever done to you?
  15. What would you change about your parenting style compared to how your own parents raised you?
  16. When was the last time you learned something you wish you never found out about?
  17. If you were to get a post-graduate degree in any field other than the one you’re in, what would it be and why?
  18. Do you think that children born today will have better lives than the generations before them? Why or why not?
  19. What’s the single most important and valuable human invention of all time?
  20. What do you think separates humans from other animal species to make us the ‘superior race’?
  21. What used to be cool to you, but isn’t anymore? What used to be uncool, but is now cool?
  22. What do you think your pet would tell you if it learned how to talk?
  23. What’s the worst waste of money that you’ve ever experienced?
  24. What bad habit do you have that’s simple, yet hard to give up?
  25. Have you ever regretted something you said or did? What did you do to cope with the regret?
  26. What’s the silliest thing that you’ve ever been upset about?
  27. What to you are the three golden rules of using social media?
  28. What life skills are rarely taught, but you think would be most useful in the real world?
  29. What scientific discovery or invention do you think would change the way the world works?
  30. What do you love spending money on that you consider more of a luxury than a need?