Questions that go a little deeper to get to know someone: What is your favorite childhood memory? What is one thing you worried and stressed about that ended up being no big deal? What skill do you wish you could master?
What is one thing no one realizes about you? If you could bring one musician back from the dead, who would it be? When is the last time you used YOLO as an excuse to do something? Have you ever had a near-death situation? What makes you laugh no matter what? What is your most prized possession? What would your perfect day look like? Did you have a happy childhood? Do you get along with your parents? Do you get along with your siblings? Are you ever judgmental?
Where do you see yourself in ten years? Where your parents strict? Have you ever cheated on a test? How would your family describe you? What do your friends love most about you? What is the last thing that really moved you? Have you ever been caught in a lie? Have you ever made a huge drunken mistake? Have you ever had surgery? What is a risk worth taking? Is there anyone you admire? Do you believe in a higher power? What is a cause you truly believe in? Do you want to have kids someday?
Is it better to be nice or important? What is your biggest guilty pleasure? How have you changed since your teenage years? Is there a mistake you seem to make over and over again? What do people usually come to you for when they need advice? Do you have any strange phobias? Have you ever been in a physical fight? Does getting older scare you? What is something you consider absolutely unforgivable? What did you love most about your hometown?
Do you believe in reincarnation? What is something that makes you feel like a kid again? How do you deal with stressful situations?
Are you good at debates? What advice would you give your teenage self? What is something you always procrastinate on? What is the title of the story of your life? Are you a spender or a saver? If you could get rid of one technological item, what would it be? What annoys you most about people? What qualities do you value in your friends?
What do you have no patience for? What is your favorite family memory? What is the best thing that happened to you this year? What is one goal you hope to achieve in your lifetime? Very deep and personal questions to get to know someone: Were you ever bullied?
Have you ever been a bully? What was your biggest childhood fear? What are people always surprised to discover about you? What is one thing you wish you knew as a child? Have you ever had your heart broken? What was the worst part of your childhood? What surprises you the most about people? What is your biggest regret in life? What is the one way you sabotage yourself?
Have you ever burned any bridges that you regret? Do you have any recurring dreams? When is the last time you felt truly, deeply happy?
Would you change anything about your family? What is one thing you wish you could go back and do again? Have you ever been in love? Are you a confident person? What keeps you up at night? What are your biggest insecurities? What are your greatest fears? What gives your life meaning? Would you say you truly love yourself? Have you ever been cheated on? What is the most important life lesson for someone to learn? Have you ever cheated on someone? When was the last time you had a good cry?
Have you ever been addicted to something? Has anyone close to you passed away? What is your biggest weakness? What do you wish you could be better at? If you could go back and re-do the last five years, what would you do differently? What always angers you? Have you ever experienced a trauma? Have you ever been on medicine for a mental issue?
Have you ever seen a therapist? Do your parents have a happy marriage? Have you ever hit rock bottom in life? Have you ever been in serious trouble? What makes you feel truly alive? What was a defining moment in your life? Do you believe in an afterlife? What is something you did once and will never do again? What is something you have strong opinions about? Questions to ask a guy you like: