There are so many situations where a set of deep questions to ask can come in handy. After all, one of life’s greatest pleasures is asking a group of close friends an especially good question that’s met with a few solid beats of (contemplative) silence. Having a vault of deep questions to ask is going to reward you time and time again, from awkward party silences to weird dinners with family. And within the greater world of queries, there are levels to the simple category of “deep questions.” It’s important to know your audience, whether you’re chatting with friends or in a long conversation with a crush. With these questions in your pocket, you may just beawarded “Best Conversationalist.”
Ahead, we gathered our favorite deep questions to ask people by relationship type. Go forth and talk!
In this article:
- Deep Questions to Ask Your Partner
- Deep Questions to Ask Friends
- Deep Questions to Ask Your Crush
- Deep Questions About Life
Deep Questions to Ask Your Partner
- Who is your biggest role model?
- What does a healthy relationship look like to you?
- What is your favorite part about our relationship?
- What does the ideal date look like?
- What’s your love language?
- What is one thing that will get on your nerves immediately?
- What do you think happens after we die?
- Do you believe in alien life?
- What are you most afraid of?
- What is one thing that never fails to make you feel better?
- What do you get out of traveling?
- What are your biggest priorities in life?
- Who are you most similar to in your family?
- What do you dread doing?
- How do you cope when you’re upset?
- What do you most look forward to every day?
- What was your proudest moment?
- Have you ever lost someone close to you?
- Are you spiritual?
- Do you have a life philosophy?
- Do you believe in fate?
- Do you think you’re honest with yourself?
- What’s something you loved that your parents did?
- And what’s something your parents did that you hated?
- What’s something you really enjoy now that you used to hate?
Deep Questions to Ask Friends
- Who would narrate an audio book memoir about your life?
- Who is your dream date and why?
- If you could change anything about your life immediately, what would it be?
- What’s your greatest skill?
- What hobby have you always wanted to pick up?
- What does your dream house look like and what’s inside?
- How do you think one million dollars can be best spent?
- How do you hope people perceive you?
- What’s your dream job?
- What is one thing that brings you joy?
- What’s the best advice someone has ever given you?
- What is your worst memory?
- Have you ever lost a best friend?
- What makes you feel the most seen?
- Do you think keeping secrets is a bad thing?
- What would you eat if you knew it was your last meal?
- If you could ask anyone, dead or alive, 10 questions, who would you choose?
- When do you feel the most free?
- What do you consider the worst crime someone can commit?
- Do you think there’s any good in holding a grudge?
- What do you consider to be the most important book on the planet?
- What or who inspires you the most?
- What is the craziest thing you’ve ever done for another person and why did you do it?
- Are you a pessimist or an optimist?
- When was the last time you cried?
Deep Questions to Ask Your Crush
- What’s your favorite thing about your best friend?
- What do you want to do in your future career?
- Where is the most stunning place you’ve ever visited in person?
- Is flirting considered cheating?
- What is something you think people might automatically assume when you first meet you?
- What is one thing you wished you knew as a younger version of yourself?
- What do you consider the best bad decision you’ve made so far in life?
- What is one thing you would try if you knew you wouldn’t fail?
- When was the last time you tried something new?
- Who do you most compare yourself to?
- Is there a big life lesson you learned the hard way?
- What is one thing you wished you spent more time doing?
- What is one thing you know you’re wrong about?
- What is your biggest blind-faith belief?
- If you could give a one-hour presentation on something, what would it be?
- What’s the worst piece of advice you’ve ever gotten?
- How do you handle stress?
- What’s been the most defining moment of your life so far?
- Have you ever had a deepest fear come true?
- Does everyone truly deserve a second chance?
- What’s the strangest encounter you’ve ever had?
- What single thing makes you feel the most alive?
- When is the last time you felt lost?
- What’s something you really love about yourself?
- What do you consider the scariest question?
Deep Questions About Life
- Do you think there’s a greater meaning to life outside of simply living?
- Would you choose never having to worry about money or being happy for the rest of your life?
- Do you think travel is important? Why or why not?
- What should be the biggest priority in life?
- Do you believe that some things are simply inexplicable?
- Should toilet paper be hung over or under?
- Would it actually be cool to live forever?
- Do you think dreams have deeper meanings?
- What is one thing you think holds you back?
- Does love at first sight exist?
- Is it easier to love or hate someone?
- Do you think it’s possible to do a completely selfless deed?
- Do you think a single moment has power to change the world?
- How do you determine right versus wrong?
- How do you define happiness?
- Do you believe all people are born good?
- What do you think the actual “American Dream” is?
- What impact do you want to make on the world?
- Why do you think we’re afraid of things?
- What is art and why do you think it’s so important?
- Why are some people super creative and others aren’t?
- Is it always rude to ignore someone in public?
- Do you actually think the world will end and if so, how will it happen?
- What do you think it means to be a human?
- What makes people unique?
- Are having problems always a bad thing?
