Intriguing Personal Questions to Get to Know Someone

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October 26, 2020

When you meet someone for the first time, it can be challenging to keep the conversation going. On one hand, you don’t want to seem like you’re prying by asking too many questions. On the other, you don’t want to come across uninterested. So what do you do?

The trick is to identify deep questions to ask someone that strikes the right balance. We’ve compiled a list of questions you can ask to break the ice. Whether you’re eyeing a new girl or guy or you want to make a new friend, we’ve got you covered.

Deep Questions to Ask a Girl

You’ve met a girl you like. If you’re like most guys, every part of your being wants to approach her and begin connecting. However, you’re overcome by the fear that stops most men in their tracks. What do you tell her? How do you start the conversation? Most importantly, how do you keep the conversation interesting enough and leave knowing them better?

This situation can be a tough nut to crack. But it doesn’t have to be. With the right approach, you’ll not only get her attention but also the answers you need to know her better. Here are some interesting deep questions you can ask someone you like once you’ve made that connection.

  1. What’s your view on religion?
  2. Do you believe in reincarnation?
  3. Would you rather be a single parent or have a complete family?
  4. What’s your view on gender roles in relationships?
  5. Have you ever asked a guy out?
  6. What do you look for in a man?
  7. Would you date a broke man?
  8. Where do you see yourself in the next 5 years?
  9. How would you handle financial conversations in a relationship?
  10. Would you be comfortable dating a man who earns more money than you?
  11. Which family member are you closest to and why?
  12. What’s the biggest lesson you’ve learned in life?
  13. What’s the most significant challenge you’ve faced and how did you overcome it?
  14. Do you believe your childhood upbringing influenced the person you were today?
  15. If your parents disapproved of your partner, would you go ahead and date them?
  16. What are your relationship deal breakers?
  17. What lessons did you learn from your last relationship?
  18. Have anyone broken your heart before?
  19. How do you cope with stress?
  20. What’s your biggest motivator in life?
  21. Do you believe in second chances in relationships?
  22. What’s your view on cheating in relationships?
  23. What has your parents’ relationship taught you about relationships?
  24. Do you have any regrets? What would you do differently if given a chance?
  25. When you’re in a terrible mood, do you prefer solitude or for someone to cheer you up?

Deep Questions to Ask a Friend

When you’re younger, making friends is quite effortless. All you have to do is be on the same playground and you’ll connect. It’s different when you’re older. You have to approach the situation differently lest you come across as an intruder in someone’s space. So, what do you do when you’ve met someone you want to be friends with?

Starting with a “hi” or “hello” always breaks the ice. However, you need to keep up the conversation to create an opportunity to connect. Consider these questions.

  1. What’s your favorite hobby?
  2. Which TV series are you currently watching? What’s your take on it?
  3. Do you play any instruments?
  4. Where did you grow up?
  5. What’s your spirit animal and why do you relate it with it so much?
  6. When was the last time you went camping?
  7. How long have you lived in this area?
  8. Who inspires you the most in your life?
  9. Would you choose fame if it didn’t come with wealth?
  10. What’s your view on the Black Lives Matter movement?
  11. What does a perfect day look like to you?
  12. What’s your favorite childhood memory?
  13. What crazy thing have you done for a friend?
  14. Do you believe in a large circle of friends or a few friends you trust?
  15. Would you live in an area where you don’t have any close friends or family nearby?
  16. How was your high school life?
  17. Do you consider yourself religious or spiritual?
  18. What do you wish most people knew about you but they don’t?
  19. What’s your favorite book so far?
  20. Are you an outdoors or indoors kind of person?
  21. Would you give your significant other your phone passwords? Why?
  22. Do you believe there’s a right age to get married?
  23. Do you prefer intelligence or beauty?
  24. What’s your favorite memory with your closest friends?
  25. What’s your idea of the perfect date?

Deep Questions to Ask a Guy

If you’re a woman, finding personal questions to get to know someone can be a bit tricky if it’s a guy. Many people shy away to ask and answer deep questions, and as a result, most connections are surface level. So if you want him to open up, it’s all about asking the right questions that have the potential to reveal his true personality.

It’s even harder to keep the conversation going because you don’t want to come across as too eager or desperate. But don’t let this fear stop you from making what could be a lasting connection. The following questions work when you’re making the first move or simply want to know the guy you’re dating better.

  1. How did your last relationship end? Do you think you were to blame?
  2. What’s your view on online dating?
  3. Are you close to your parents?
  4. How’s your relationship with your family?
  5. Would you date a woman your family disapproved of?
  6. Would you be comfortable dating a woman who earns more money than you?
  7. What do you believe is the role of a woman in a relationship?
  8. Do you believe in splitting household expenses 50/50?
  9. Whose responsibility do you think it is to discipline the children in a relationship?
  10. What do you love most about your parents?
  11. Who is your favorite artist?
  12. What’s the worst thing you’ve gone through?
  13. What are your long-term goals?
  14. What are your short-term goals?
  15. How important is sex in a relationship?
  16. What’s your greatest achievement?
  17. What are your resolutions for this year?
  18. Have you ever lost someone close to you?
  19. What’s one thing most people don’t understand about you?
  20. What do you think makes a person ready for marriage?
  21. Would you stay with someone who cheated on you?
  22. Do you expect to know your girlfriend’s whereabouts? Why?
  23. Would you relocate to follow your partner’s dreams?
  24. Would you consider being a stay-at-home dad?
  25. Would you take your partner’s religion?

Deep Questions to Ask Colleagues

Making friends at work is a good move. Time moves faster when you have a friend to share your victories and challenges with. Besides, work relationships can be crucial when you need referrals or connections for jobs. Therefore, as hard as it may be to make new friends you have to try, especially if you’re new.

The best thing about the workplace is that you can take your time. Say hello a couple of times and when you’re sure a friendship is brewing, get to know the person better. The following questions will be interesting water cooler conversations.

  1. How do you unwind after a long day of work?
  2. What’s your most memorable vacation?
  3. Do you work on your days off or when you’re supposed to be off the clock?
  4. What’s your idea of a perfect day?
  5. What’s your view on God and religion?
  6. Which book are you reading?
  7. What’s your favorite food?
  8. What do you wish you did often but never get to do?
  9. If you could only eat ice cream or chocolate, which one would it be?
  10. What are you hoping to achieve this year?
  11. What’s your idea of a perfect retirement life?
  12. What do you do when you’re not at work?
  13. How long have you been working at this company? What do you love about it?
  14. If you could change something about yourself, what would it be?
  15. Do you confront things head on or ignore them until it becomes too much?

Wrapping Up

There you have it, intriguing and deep questions to keep the conversation going with spouses, friends, and colleagues. When you ask these questions you’ll notice the conversation broadening naturally and more questions coming in. Remember to leave room for the other person to get to know you as well. That’s how you build lasting and meaningful connections with your loved ones.

Kate Skurat

Kate Skurat

Licensed Mental Health Counselor

Washington, United States

Kate has a B.S. in Psychology and M.A. in Clinical Psychology from Pepperdine University and has worked in healthcare since 2017. She primarily treated depression, anxiety, eating disorders, trauma, and grief, as well as identity, relationship and adjustment issues. Her clinical experience has focused on individual and group counseling, emergency counseling and outreach. Read more.

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