Deep questions to ask in an intimate conversation:
If you could change anything about your upbringing, what would it be?
What is too serious to joke about?
Your house, which has everything you have, is on fire. Once you've saved your loved ones and pets, you have time to safely make the final push to save at least one item. What could it be? Why?
What are you most grateful for in your life?
Of all your family members, whose death worries you the most? Why?
If you died tonight without being able to communicate with anyone, what would you most regret not telling someone?
If you knew that in a year you would suddenly die, would you change anything in your current life? Why?
What are you most afraid of?
If you could quit your job right now to pursue your passion, what would you do?

Personal questions:
When was the last time you cried in front of another person?
What is the biggest achievement in your life?
What is your most treasured memory?
What is your worst memory?
Do you think that your childhood was happier than others?
How do you feel about your relationship with your mother?
Is there anything you've been dreaming of doing for a long time? Why don't you do it?
Who has influenced your life the most?

Romantic questions:
Do you have cute fantasies?
What does love mean to you ?
How many times have you been in love?
How to know that you are in love?
What is your favorite romantic comedy and why?
Do you like holding hands?
What is the best love story you have ever heard?
Do you believe in the existence of kindred spirits?
What is your favorite love song?
Do you like when they cook for you?