Questions to Ask Someone to Get to Know Them More Deeply
- What is the most trivial thing about which you have a strong opinion?
- What is one thing you’re good at that people don’t expect?
- What is a childhood habit or preference that you’ll never outgrow?
- Ideally, how would you spend your birthday?
- What is something you’ve done / felt / seen / etc that you wish you could experience again for the first time?
- What is the luckiest thing that has happened to you? What is the unluckiest thing that has happened to you?
- Have you ever been told that you have a doppelgänger? If so, who is it?
- Do you feel like you are better than average at dealing with needy people in your life?
- To what extent do you consider yourself to be an argumentative person?
- What is a temptation or habit you struggle to overcome?
- Would you describe yourself as a more clean or messy person?
- What is one question you wish people would ask you more? What is one question you wish people would ask you less?
- What makes you feel most accomplished?
- What trait are you most grateful to have that you didn’t necessarily have to work for?
- Are you more of a starter or a finisher?
- What’s the nicest compliment you’ve received lately?
- When was the last time that you astonished yourself?
- What is something that you are improving at?
- What makes you feel the most competent?
- What’s one thing about your life that you’d never change for me or anyone else?
- How important are birthdays and anniversaries to you? How do you like to celebrate?
- What question do you most hate being asked?
- What, if anything, is too serious to be joked about?
- Have you gone through any phases in your life? What is the most notable one?
- What stereotype are you most like?
- What is something that’s difficult for you but easy for most other people?
- What is something that’s easy for you but difficult for most other people?
- What is something you enjoyed doing but would never do again?
- What object best defines who you are?
- What is something your brain wants to convince you to do but you have to fight it?
If you love this category, you'll also enjoy Chatterbox questions from these categories as well!
