41 Very Deep Questions to Ask Someone Before You Get Close to Them

Building a close connection with someone is a journey, and asking deep questions can be a great way to understand them better.

With that in mind, we’ve compiled a list of very deep questions to ask someone before getting close to them.

These questions go beyond the surface, helping you uncover meaningful insights and strengthen your bond.

Let’s dive into these conversation starters to help you discover more about the person you’re getting to know.

Very Deep Questions to Ask Someone Before You Get Close to Them

Here are 41 deep questions to ask someone to get to know them better:

1. What Are You Most Proud Of?

That is a great question to ask someone if you want to get to know them on a deeper level. It can help you understand what motivates and drives them.

Additionally, it can give you insight into their values and how they view themselves.

That question can also help build rapport and trust between you and the other person.

3. What Is Your Biggest Fear?

This question can help you to understand what someone is most afraid of and what they worry about the most.

That can give insight into the person’s personality and how they react to stress or difficult situations.

It can also help you to understand what kinds of things they are not comfortable with and what types of things make them uneasy.

4. What Is Your Biggest Regret?

This question can help you to understand what someone regrets the most in their life.

That can give you some insight into their values and what they believe is essential to them.

It can also help you to understand what kind of person they are and how they deal with mistakes or disappointments.

5. What Is Your Happiest Memory?

This question can help you to understand what makes someone happy and what they enjoy doing.

That can give you insight into the person’s personality and how they like to spend their time.

It can also help you to understand what kind of things make them happy and what kind of things make them sad.

6. What Are Your Values and Beliefs?

That’s an important question to ask someone before you get close to them.

By understanding the person’s values and beliefs, you will be able to understand them as a person better.

That can help you determine if you have compatible values and beliefs.

7. What Are Your Goals and Aspirations in Life?

That is another essential question to ask someone before getting close to them.

By understanding the person’s goals and aspirations, you will better understand what they are striving for in life.

That can help you determine if you share similar goals and aspirations.

8. What Are Your Thoughts on Relationships?

That is a crucial question to ask someone before getting close to them.

By understanding the person’s thoughts on relationships, you will better understand how they view relationships.

That can help you determine if you have compatible views on relationships.

9. Who Do You Consider a Good Human Being?

That is a deep question that can help you get to know someone deeper. It can help you understand their perception of life.

10. Have You Ever Had Your Heart Broken by Someone?

That is a question that must be asked. If someone breaks their heart, they are likely to develop trust issues.

Also, knowing if someone has experienced heartbreak helps you appreciate their vulnerability and past relationship struggles, fostering empathy and a deeper connection.

11. What Might You Change About Yourself if You Could?

By asking about self-improvement, you’re inviting them to share their aspirations for personal growth.

This question opens the door to discussing self-awareness and the willingness to evolve, providing insights into their character and future goals.

12. Which Foods Are Your Favorites and Least Favorites?

Exploring someone’s culinary preferences goes beyond just sharing meals. It can reveal cultural influences, lifestyle choices, and potential shared interests.

It’s a simple yet effective way to connect on a personal and daily life level.

13. What Is Your Proudest Achievement?

Inquiring about their proudest moment allows them to share significant accomplishments and milestones.

This question offers a glimpse into their values, passions, and the type of achievements that bring them a sense of fulfillment.

14. What Are Your Interests?

Understanding someone’s interests is crucial for building common ground.

It helps you discover shared hobbies or activities, fostering the potential for future bonding experiences and demonstrating your genuine interest in getting to know them.

15. What Do You Consider to Be the Ideal Relationship?

This question factor into their relationship expectations and values. It provides insights into their communication style, emotional needs, and the foundation they believe is essential for a strong and fulfilling connection.

16. Who Do You Consider to Be a Good Person?

By asking about their perception of goodness, you gain insights into their moral compass and the qualities they admire in others.

This question touches on their values, ethics, and the standards they hold for themselves and those around them.

17. Do You Have Faith in God?

Exploring their beliefs in a higher power or spirituality is a more profound inquiry.

It goes beyond surface-level conversations, delving into their worldview and providing a glimpse into their spiritual or philosophical foundation, which can be integral to understanding their identity.

18. Do You Support Gay Rights?

This question is about understanding someone’s stance on equal rights for people who are gay.

It digs into their views on inclusivity and fairness, which can be crucial in knowing their values regarding diversity and acceptance.

19. Do You Enjoy Discussing Politics?

By asking about their interest in political discussions, you’re exploring their engagement with important societal matters.

It can reveal if they stay informed about current events and if they enjoy exchanging ideas on topics that shape the world around us.

20. Do You Have a Favorite Football Team?

This question aims to uncover their sports preferences, specifically in football (soccer).

It’s a light-hearted way to connect over shared team allegiances or to learn about their passion for sports, providing potential common ground for future interactions.

21. What Are Your Favorite Movies?

Inquiring about their favorite movies is a way to tap into their entertainment preferences.

It can lead to discussions about storytelling, and genres they enjoy, and might even spark recommendations for movies you both could watch together.

22. Do You Believe That People Should Be Free to Express Themselves, Even if They Are Offensive?

This question addresses the concept of freedom of expression and tolerance. It explores their perspective on whether everyone should have the right to share their opinions, even if those opinions might be hurtful to others.

It opens up a conversation about the balance between freedom and responsibility.

23. What Are Your Thoughts on Your Country’s Current Political Situation?

By asking about their views on the political climate of their country, you’re delving into their concerns, hopes, and opinions regarding governance.

This question can lead to deep discussions about social issues, policies, and their vision for the future.

24. What Would You Do if You Won a Million Dollars?

Inquiring about their hypothetical use of a large sum of money provides insights into their priorities and aspirations.

It’s a fun and imaginative question that can lead to discussions about personal goals, dreams, and the things that matter most to them.

25. What Type of Music Do You Enjoy?

This question is about understanding their musical preferences, whether it’s energetic pop, soulful jazz, or rocking out to some classics.

It can lead to conversations about concerts they’ve attended, favorite albums, and the emotional connection they have with certain songs.

26. Do You Believe In the Supernatural?

By asking about their beliefs in the supernatural, you’re exploring their thoughts on things like ghosts, magic, or unexplained phenomena.

This question can open up discussions about spirituality, personal experiences, and cultural beliefs.

27. What Is Your Most Terrifying Experience?

Inquiring about their most terrifying experience invites them to share a challenging moment from their past.

This question can lead to deeper conversations about resilience, personal growth, and the lessons learned from facing fear.

28. Do You Love Expensive Cars?

This is asking if they have a strong liking for luxurious and expensive cars. It’s a way to understand their taste in vehicles and possibly dig into discussions about hobbies, aspirations, or experiences related to automobiles.

29. How Many Children Do You Want?

This question explores their thoughts on family planning. It can lead to discussions about their values, priorities, and dreams for the future, providing insights into their long-term goals and personal aspirations.

30. What Would You Do if You Could Be God for a Day?

This imaginative question sparks creativity and reveals their aspirations for positive change.

It can lead to discussions about their values, desires for a better world, and the things they find important if they have the power to influence events.

31. Which Musician Is Your Favorite?

By asking about their favorite musician, you’re exploring their musical tastes and influences. It can lead to shared interests, recommendations, and perhaps even discovering new artists together.

32. Who Are Your Favorite Actors and Actresses?

This question examines their entertainment preferences, possibly leading to conversations about favorite films, genres, and memorable performances that have left an impact on them.

33. When You Die, What Do You Want People to Remember About You?

This question is about thinking ahead to the legacy someone wants to leave behind.

It helps you understand their values and what they find important in life, allowing for a deeper conversation about personal aspirations and impact.

34. How Frequently Do You Pray?

Asking deep questions about faith and prayer gives you insight into their spiritual practices and beliefs, fostering an understanding of their connection to faith.

35. Which Is More Important in a Relationship: Love or Money?

This question explores their priorities in a relationship. It helps you understand whether they value emotional connection and love more or if financial stability is a crucial factor.

It’s a way to see into their views on relationships and what matters most to them.

36. Do You Believe In the Afterlife?

By asking about the afterlife, you’re exploring someone’s beliefs about what happens when life ends. It can lead to discussions about spirituality, religion, and the concept of an existence beyond our current life.

37. Can You Marry Someone Who Has Had Multiple Sexual Partners in the Past?

Asking these types of deep questions opens up a conversation about values, trust, and acceptance.

It also explores their thoughts on how someone’s past experiences may or may not impact a future relationship.

38. Do You Have a Favorite Author?

This question is about finding out if there’s a writer whose books they like. It can lead to interesting conversations about stories, characters, and the kind of writing that resonates with them.

39. What Do You Like About Your Best Friend?

By asking this, you’re giving them a chance to share what makes their closest friend special. It could be their kindness, humor, or support. It helps you understand the qualities they value in people.

40. Tell Me About Your Childhood

This question invites them to talk about when they were a kid. They might share funny stories, memorable experiences, or important people from their past.

It can deepen your understanding of their background and shape who they are today.

41. Tell Me About Your Best Subjects

Asking about their best subjects is about learning which school or college topics they enjoy the most. It can lead to discussions about their interests, passions, and possibly career aspirations.

Understanding what subjects they excel in gives you insight into their academic side.

Final Thought

Every day we get to meet new people and try to get to know them, some on a shallow level while others deeper.

Asking the above Deep Questions will help you get to know someone better so that you can decide whether they suit you or not.

Remember, open and honest communication is the key to forging lasting connections.

So, embrace the opportunity to ask these thought-provoking questions, and enjoy the journey of getting to know someone on a deeper level.