- Because talking about the small stuff is boring.
These are some devilishly deep questions to ask almost anyone. Who really wants to talk about the weather anyway?
- What was your best birthday?
- If you could make one wish right now, what would you wish for?
- What was something you enjoyed as a child but now cringe at the thought of? Can you pinpoint why that changed?
- Are you religious or spiritual?
- Would you consider yourself a generous person?
- Are there any medical concerns that run in your family?
- Do you usually stay friends with your exes?
- Who was your favorite teacher, and why?
- What are your thoughts on online dating or apps like Tinder?
- What is your idea of a perfect vacation, and why?
- What is one dream you have yet to accomplish?
- Which would you rather do: wash dishes, mow the lawn, clean the bathroom or vacuum the house?
- What do you like to do that is traditionally considered masculine?
- What if you found out that you were the star of the Truman Show?
- What scrambles your brain every time you think about it? This is one of the best deep questions.
- If you could change your first name, what do you wish it would be?
- What was the worst phase in your life?
- What event from the past do you most want to see a recording of?
- What do you really wish you knew when you were younger?
- Why did your last relationship end?
- What are you most grateful for?
- Where do you see yourself in five years?
- Are you confrontational?
- What is the craziest thing you’ve ever done and would you do it again?
- What do you wish you could re-live in your lifetime?
- What gross and unhygienic things do people do that bother you?
- What’s the best piece of advice someone has given you?
- Do you prefer being warmed when you’re too cold or being cooled when you’re too hot?
- If you could be someone else for a day, who would it be and why?
- Why do you think we dream?
- Do you believe in second chances?
- If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?
- If money was no object, what would you do all day?
- Do you like or dislike surprises? Why or why not?
- Do you consider yourself an introvert or an extrovert?
- Do you consider yourself a pessimist or an optimist? This truly sets people apart from others and is one of the best deep questions.
- What was the worst phase you went through in life?
- Are you passionate about collecting anything?
- Do you think you put a lot of weight into first impressions?
- How do you think the world should change?
- Would you rather win the lottery or work at the perfect job? And why?
- What’s your philosophy in life?
- What’s an innocent mistake you made that had dramatic consequences?
- How often do you think about death?
- What are you most thankful for?
- What did your past relationship teach you?
- Would you ever take back someone who cheated?
- When do you hope to have life figured out?
- Do you consider yourself an introvert or an extrovert?
- If when you died, you got put into a room for eternity with people who died the same way, how would you want to die?
- If you could choose to do anything for a day, what would it be?
- Are you a morning person or a night owl?
- What’s the emoji you use the most? And why do you think that is?
- When was the last time you cried?
- If you could be a trade sexes for a day, what would you do? Hasn’t everyone thought of these deep questions?
- Would you go through a boyfriend’s phone if you could?
- What body features do you pay the most attention to?
- What’s the one thing that people always misunderstand about you?
- Do you believe in angel numbers?
- What’s on your bucket list this year?
- What’s the best conspiracy theory you can think of?
- What crazy things will you do if you ever become rich?
- How do you feel about sharing your password with your partner?
- How would your friends describe you?
- Are you ever insecure about your sense of humor?
- Which parent are you more like, and why?
- What’s the most stress-relieving thing you can get/do for less than $20?
- What are your hobbies?
- What makes you feel accomplished?
- What did you want to be when you were small?
What do you think of these devilishly deep questions? Let me know the ones that interest you most in the comments!