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.