If you are anything like me, you love deep conversations. Deep conversations allow us to get to know someone beyond the surface level. People also tend to appreciate deep conversations. I know that I always appreciate and enjoy answering difficult and thought-provoking questions that make me really reflect on my past and the person I want to be.

I tend to ask these questions just out of habit and pure curiosity right after meeting someone. Sometimes I get so lost into a conversation that I forget about boundaries.

So, if you are trying to cross boundaries and really want to get to know someone, I have some questions ready for you covering topics from just getting to know someone, trying to better understand their character, how they are romantically and showing interest in their dreams and aspirations.

If you are just trying to get to know someone and better understand their past:

1. Did you like your childhood?

2. What was your home environment and hometown like?

3. How has your childhood shaped the person you are today?

4. What is your favorite memory from your childhood?

5. Who is your biggest influence on your life, and why?

6. What was your childhood dream(s)?

7. Were your parents involved in your life? Who was?

8. What was your biggest nightmare when you were younger?

9. Do you fear the unexpected? Or do you thrive on not knowing what life has in store for you?

10. When is your birthday? What was your favorite birthday, and why?

11. What is your most favorite thing to do?

12. What is your favorite vacation or place in the world that you have been to?

13. Did you have any struggles growing up? How did you overcome them? Who helped you? How have they helped you evolve into the person you are today?

14. What is your favorite book? Why is it your favorite? (Did it help you escape reality? Better understand a reality different from your own? Make you more aware of different issues that aren't prevalent to your life?)

15. What were your childhood friends like? What did you do together?

16. What kind of person do you think you are in your friend group?

17. Are you into astrology? Do you think your zodiac sign is a fair representation of you?

18. What is your relationship like with your family?

19. What is your favorite kind of weather? Do you love the heat and sunshine, stormy, rainy weather, or the cold and snow? Why?

20. Would you rather be outside being adventurous and in nature, or inside and playing video games and watching TV?

Trying to better understand their character:

1. How would you describe yourself in three words, and why?

2. What do you spend your free time doing?

3. What is your favorite movie/tv series?

4. What is your favorite trait about yourself, and why? What is your least favorite?

5. Do you tend to overthink? Why do you think you overthink?

6. Are you an introvert or an extrovert?

7. Do you like to be around big crowds of people, or do you like small groups?

8. Do you like small towns, or big cities, and why?

9. What makes you feel the most at peace?

10. What do you do when you feel disrespected? Are you confrontational or just let it go?

11. What do you think determines happiness? What makes you happy?

12. What scares you the most about the world? How would you combat or fix it?

13. Does adventure excite you?

14. Do you fear change?

15. What are three things that excite you about life?

Thank you, Beckah M.

16. What are things that make you nervous?

17. Do you feel understood? Or do you feel that people misunderstand and jump to conclusions about you? If so, how?

18. What kind of friend do you try to be?

19. What is your favorite song, album, artist, genre of music? Why is it your favorite?

20. What song would you say you can relate to the most or you can identify with the most?

Trying to better understand them romantically:

1. Does sending the first text or reaching out first scare you?

2. Do you fear rejection? Or do you always shoot your shot with your heart on your sleeve?

3. What are your soft and hard limits?

4. How many relationships have you had? What was your longest or most serious?

5. Have you ever been in love? Do you think you can be in love more than once?

6. What does being in love mean to you? In your opinion, what's the difference between being "in love" and "having love for someone"?

7. How do you feel about PDA? Do you like being affectionate in public, or would you rather keep the affection lowkey and just for you and your S.O.?

8. Have you ever had your heartbroken? How has it impacted you?

9. What is your idea of a perfect date?

10. What are qualities you look for in someone you want to date, or even look for in a lifelong partner?

11. What does sex mean to you?

12. Who is your celebrity crush?

13. Is there a relationship that you look up to?

14. What are your fantasies?

15. What does being intimate mean to you? Do you fear intimacy?

16. How do you like to be loved?

17. How can you be pleased or satisfied sexually?

18. Do you tend to push people away before they get too close? If so, why do you think you do?

19. What's your favorite love song?

20. Are you a relationship person? Or do you not prefer to not use labels? Why?

If you want to better understand their dreams and aspirations:

1. What do you want from life?

2. What is your biggest dream?

3. What are your short term goals? Long term goals?

4. Do you want to explore the world? If so, what do you want to explore?

5. What is your dream job?

6. If you could get a plan ticket for anywhere, where would you want to go? What would you do?

7. If you had all of the money in the world, what would you do with it?

8. When you are older, what are the memories you think you'll look back on?

9. What do you think is important when thinking about your future? Will it be a college degree? Adventuring? Traveling? Being rich? Being a minimalist?

10. What do you want your life to be like in 5, 10, 15+ years from now?

11. Are you hoping to settle down? Do you want to travel, and then settle down? Or vice versa?

12. Do you want to get married? What do you hope for in a marriage?

13. Do you want to have a family someday? What will your family look like? Will you adopt or foster?

14. What do you believe your purpose in life is?

15. Who has been the biggest influence in your life?

16. Do you feel you have something to prove? Do your parents expect a lot from you? Do they have a say in how you live your life?

17. Why did you choose the job, major or professional field you did or are interested in?

18. Would you rather live safe and practical, or live uncertainly and on the edge?

19. What is the most important part of life in your opinion? Is it love? Success? Family? Money?

20. How do you hope people see you as a person? How do you want to be remembered?