If you were going to be a close friend to me what should I know?
Am I like you expected me to be? Why or why not?
Share an embarrassing moment from recent life.
Tell me something out of your comfort zone.
Describe your worst heartbreak. What did it teach you?
When did you last cry? Why?
What do you think I need to let go of?
How can I best be there for you during this chapter in your life?
What are you trying to prove to yourself?
Have I ever hurt you? How?
What song reminds you of me?
If you were to die tonight with no opportunity to communicate with anyone, what would you regret not telling me? Why haven't you told me?
What is one personality trait your parents passed down to you that you wish they hadn't?
What is one personality trait your parents passed down that you are glad they did?
What do you think is the hardest part about loving you?
What would your younger self not believe about your life today?
What is the worst non-physical pain you have ever felt?
What do you think I should know about myself but am unaware of?
How do you think we compliment each other?
What do you think is one thing I could do to drastically improve my life?
What do you think is my biggest weakness?
Based on what you have learnt today, has your perception of me changed? How?
What would be the perfect gift for you?
What would make you feel closer to me?
How would you describe me to someone who doesn't know me?
Do you think we met for a reason? What reason?
What do you think is my biggest fear?
What do you think I need to hear right now?
When is the last time you said 'I love you' and meant it?
What lesson will you take away from our conversation?
What would you trust me to give advice on? Why?
When this game is over, what do you want to know more about?
Do you think everyone has a calling? Do you think i've found mine?
How can I add more happiness in your life?
Is there closure you never got to have?
Which questions were you most afraid to answer?
Which answer of mine made you happy?
What has this conversation taught you about yourself?
What is something you are really passionate about but don't tell anyone?
What is a dream you let go of, but it hurts?
What is one thing you would change about society?
What's a chance you wish you took?
What do you wish people knew about you?
What's an apology you never got to give?
What do you owe yourself?
Describe your lowest moment in life. How did it help you grow?
What do you wish people could see?
When do you feel most like you?
What past trauma do you still deal with today?