Thought-Provoking Questions to Ask Yourself or Anyone

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If you could live one day of your life over again, what day would you choose?

What can money not buy?

When you think of ‘home,’ what, specifically, do you think of?

What is your most prized possession?

Is there ever a time when giving up makes sense?

What makes you proud?

Where do you find peace?

When have you worked hard and loved every minute of it?

Who do you trust and why?

When does silence convey more meaning than words?

How do you spend the majority of your free time?

What is your greatest skill?

What’s the next big step you need to take?

What are you looking forward to?

Who is the strongest person you know?

If you could take a single photograph of your life, what would it look like?

What are your top three priorities?

Why do we admire sports players?

What do you see when you look into the future?

What is the most valuable life lesson you learned from your parents?

What are your simple pleasures?

What will you never do?

What is your earliest childhood memory?

What’s the best part of growing older?

What’s been on your mind most lately?

What chances do you wish you had taken?

What motivates you to go to work each day?

What is your greatest strength and your greatest weakness?

When was the last time you lied? What did you lie about?

What made you smile this week?

What do you do with the majority of your money?

When was the last time you lost your temper? About what?

When you look into the past, what do you miss the most?

What is the most spontaneous thing you’ve ever done?

What worries you about the future?

What one ‘need’ and one ‘want’ will you strive to achieve in the next twelve months?

What life lessons did you have to experience firsthand before you fully understood them?

What do you do to relieve stress?

What’s the best decision you’ve ever made?

What’s your best true story that you enjoy sharing with others?

Right now, at this moment, what do you want most?

What’s the most important lesson you’ve learned in the last year?

Based on your current daily actions and routines, where would you expect to be in five years?

Through all of life’s twists and turns who has been there for you?

What or who has been distracting you?

What are you looking forward to in the upcoming week?

Who is your mentor and what have you learned from them?

What’s something most people don’t know about you?

When you have a random hour of free time, what do you usually do?

What makes you weird?

If you could relive yesterday what would you do differently?

What did life teach you yesterday?

What have you done that you are not proud of?

How would you spend your ideal day?

What is the best advice you have ever received?

If you had to be someone else for one day, who would you be and why?

Who makes you feel good about yourself?

What is your biggest regret?

Which one of your responsibilities do you wish you could get rid of?

What is missing in your life?

When you meet someone for the very first time what do you want them to think about you?

Who would you like to forgive?

At what point during the last five years have you felt lost and alone?

What do you want more of in your life?

What do you want less of in your life?

Who depends on you?

Who has had the greatest impact on your life?

In twenty years, what do you want to remember?

What are you most excited about in your life right now – today?

How many hours of television do you watch in a week? A month? A year?

What is the biggest obstacle that stands in your way right now?

What do you sometimes pretend you understand that you really don’t?

What’s something new you recently learned about yourself?

What was the most defining moment in your life during this past year?

What’s the number one change you need to make in your life in the next twelve months?

What are the top three qualities you look for in a friend?

In one word, how would you describe your childhood?

What music do you listen to lift your spirits when you’re feeling down?

If I gave you $1000 and told you that you had to spend it today, what would you buy?

What was the last thing that made you laugh out loud?

What is your biggest pet peeve?

What are some recent compliments you’ve received?

How many friends do you have in real life that you talk to regularly?

When was your first impression of someone totally wrong?

How many hours a week do you spend online?

What specific character trait do you want to be known for?

What is the number one quality that makes someone a good leader?

What bad habits do you want to break?

What do you love to practice?

What questions do you often ask yourself?

What are you an expert at?

What things in life should always be free?

What is something you have always wanted since you were a kid?

In what way are you your own worst enemy?

When did you not speak up when you should have?

What is your favorite quote?

Where or who do you turn to when you need good advice?

What have you lost interest in recently?

Who have you lost interest in recently?

What can someone do to grab your attention?

What would a new CEO do if they took over the business? What hard decisions would they make?

Who are the most important people in my life?

What stresses me out?

What would I do with my life if I knew there were no limits?

What relaxes me?

What’s my definition of success?

What type of person do I want to be?

Do the people I surround myself with add any value to my life?

What type of friend do I want to be?

What things do I value in life?

Am I holding on to something I need to let go of?

If not now, then when?

Have I done anything lately worth remembering?

Have I made someone smile today?

When did I last push the boundaries of my comfort zone?

What do I need to change about myself?

How many of my friends would I trust with my life?

Who has had the greatest impact on my life?

What’s the one thing I’d like others to remember about me at the end of my life?

Does it matter what others think about me?

When it’s all said and done, will I have said more than I’ve done?

Am I a better person today than I was yesterday?

Am I a good example for those around me?

What would I do differently if I knew nobody would judge me?

When was the last time I learned something new?

What is one thing I love the most about myself?

What do I want to be remembered for?

If I could live anywhere in the world, where would I live?

What am I most passionate about?

Can I be alone without feeling lonely?

Am I comfortable with being uncomfortable?

Where am I not being honest with myself and why?

Who is that one person I can talk to about just anything?

Am I on the right path?

Am I a good person to be around?

Does my presence add value to those around me?

When was the last time I said I love you to someone and meant it?

When was the last time I did something fun?

What is one thing I could start doing today to improve the quality of my life?

Am I a source of inspiration for my friends and family?

Who inspires me the most in this world?

If I were to give one piece of advice to a newborn child, what would it be?

Am I holding onto something I need to let go of?

Is there someone who has hurt or angered me that I need to forgive?

When was the last time I read a book that had a major influence on me?

Are there any toxic relationships in my life that need to be dealt with?

Who would I trust with my life?

Who am I most jealous of and why?

Am I a good communicator?

What upsets you about other people’s actions — and what does that say about you?

How do you handle difficult but necessary conversations?

When was the last time you felt disappointed or hurt? How did you respond?

What is your definition of happiness?

In what ways are you preventing your happiness?

When you look back at the past month, what was the most joyful moment you experienced?

When you can’t sleep at night, what do you usually think about?

How do you feel when you see yourself in the mirror?

What positive qualities do you bring into your close relationships?

What tasks and responsibilities do people at work trust you with?

What skills do you want to learn in the next five years?

What activities make you feel content, energized and fulfilled?

What are your strategies for bouncing back after a failure?

What threats and opportunities do you currently see in your life?

What could you give a 30-minute speech on with no preparation?

What do you spend too much time doing? What do you spend not enough time doing?

When you ask others for help, what do you usually ask for?

What do you think about when you’re alone?

What are three questions you wish you had definite answers to?

What is your biggest strength and your biggest weakness?

If you could change one decision you made in the past, what would it be?

How would you describe yourself in one sentence?

What compliment do you like to hear the most and why?

When do you say “I can’t” most often — and is that true?

What is the mistake you learned from the most?

When was the last time you said “no” and felt good about it?

What do you need to tell yourself today?

Who do you sometimes compare yourself to?

What life lesson did you learn the hard way?

What do you wish you spent more time doing five years ago?

Who do you love and what are you doing about it?

Do you think crying is a sign of weakness or strength?

Do you celebrate the things you do have?

Is it possible to lie without saying a word?

If you had a friend who spoke to you in the same way that you sometimes speak to yourself, how long would you allow this person to be your friend?

Which activities make you lose track of time?

When you are 80 years old, what will matter to you the most?

What makes you smile?

If you could choose one book as a mandatory read for all high school students, which book would you choose?

Would you rather have less work or more work you enjoy doing?

What’s something you know you do differently than most people?

What do you want most?

Are you more worried about doing things right, or doing the right things?

What has life taught you recently?

Where do you find inspiration?

In the hustle of your daily life, what are you not seeing?

What is your most beloved childhood memory?

If you had the chance to go back in time and change one thing would you do it?

Where would you most like to go and why?

What do you imagine yourself doing ten years from now?

What small act of kindness were you once shown that you will never forget?

Do you own your things or do your things own you?

What do you have that you cannot live without?

What are your top three personal values?

What three words would you use to describe the last three months of your life?

What is the most important thing you could do right now in your personal life?

If you could ask one person, alive or dead, only one question, who would you ask and what would you ask?

What is your number one goal for the next six months?

Are you happy with yourself?

What are three moral rules you will never break?

When you help someone do you ever think, “What’s in it for me?”

What is your greatest challenge?

If I could grant you one wish what would you wish for?

What have you read online recently that inspired you?

If you could live one day of your life over again, what day would you choose?

What can money not buy?

When you think of ‘home,’ what, specifically, do you think of?

What is your most prized possession?

Is there ever a time when giving up makes sense?

What makes you proud?

Where do you find peace?

When have you worked hard and loved every minute of it?

Who do you trust and why?

When does silence convey more meaning than words?

How do you spend the majority of your free time?

What is your greatest skill?

What’s the next big step you need to take?

What are you looking forward to?

Who is the strongest person you know?

If you could take a single photograph of your life, what would it look like?

What are your top three priorities?

Why do we admire sports players?

What do you see when you look into the future?

What is the most valuable life lesson you learned from your parents?

What are your simple pleasures?

What will you never do?

What is your earliest childhood memory?

What’s the best part of growing older?

What’s been on your mind most lately?

What chances do you wish you had taken?

Questions to ask family members, friends, acquaintances, lovers, on a date, your boyfriend, your girlfriend, your husband, your wife, your children, your parents, your grandparents, yourself, or anyone.