200+ Deep Questions & Conversation Starters to Ask Anyone

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Break the ice with new folks or get to know old friends better
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Looking to learn more about others and how they see the world? Asking thought-provoking questions is the best way to bond with someone and deepen your relationship, no matter how long you’ve known them. In this article, we’re providing the ultimate list of deep questions about life, values, beliefs, and more. We’ll also provide tips on how to ask personal questions to keep the conversation going and have an enjoyable experience.

Deep Questions to Ask Any Girl or Guy

  1. What brings you joy?
  2. What’s your idea of success?
  3. What brings out your inner child?
  4. Who would you call in an emergency?
  5. Where do you see yourself in 5 years?
  6. What are 3 things you love about yourself?
  7. If you only had one day left to live, how would you spend it?
Section 1 of 6:

Deep Questions to Get to Know Someone Better

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  1. If you want to connect with someone on a deeper level , touch on meaningful topics that move beyond the surface. Asking someone about their dreams, fears, and values is the one of the best ways to increase intimacy in any relationship. But, if the other person doesn’t feel comfortable, dating coach and matchmaker Laura Bilotta says to “respect their boundaries and move on to the next question.”
    • Who’s your role model?
    • What’s your greatest fear?
    • What’s your love language?
    • How do you handle conflict?
    • Are you spiritual or religious?
    • Are you close to your family?
    • What’s your idea of success?
    • When do you feel the safest?
    • What are you most grateful for?
    • What are you the most proud of?
    • What brings out your inner child?
    • What’s your favorite way to unwind?
    • What makes you smile on a bad day?
    • Who would you call in an emergency?
    • What would your perfect day look like?
    • What’s one thing you can’t live without?
    • What’s your favorite childhood memory?
    • How have you changed in the past year?
    • What’s the best gift you’ve ever received?
    • Do you care what people think about you?
    • What are 3 things you love about yourself?
    • What’s the last spontaneous thing you did?
    • How do you set boundaries with someone?
    • What’s one thing no one knows about you?
    • What do you miss most about being a child?
    • What’s the best advice you’ve ever received?
    • What goal are you working toward right now?
    • How would you describe yourself in 3 words?
    • Do you genuinely think you’re a good person?
    • What did you want to be when you were a child?
    • Do you think physical or emotional pain is worse?
    • What’s one thing you would change about yourself?
    • What book or film made a lasting impression on you?
    • Do you daydream a lot or stay in the present moment?
    • What’s the quickest way someone can lose your trust?
    • What are your hobbies and how did you get into them?
    • What current events or causes are you most passionate about?
    • If your life was a book, what’s the title of the chapter you’re in now?
    • If you could visit any place in the world, where would you go and why?
    • If you could step into another person’s shoes for a day, who would it be and why?
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Section 2 of 6:

Deep Questions to Ask a Friend

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  1. No matter how long you’ve known someone, there’s always something new and exciting to learn about them. These deep questions will encourage your friend to open up and be vulnerable with you, helping you discover more about their life than ever before. [1]
    • Do you like to be alone?
    • What’s your motto for life?
    • Do you think you’re brave?
    • What keeps you up at night?
    • Have you ever been in love?
    • What’s your earliest memory?
    • How do you practice self-care?
    • What’s your biggest insecurity?
    • When’s the last time you cried?
    • What’s holding you back in life?
    • Did you have a happy childhood?
    • Are you missing anyone right now?
    • What’s your least favorite emotion?
    • When’s the last time you felt alone?
    • What does happiness mean to you?
    • When do you feel the most beautiful?
    • What role does alcohol play in your life?
    • What’s your most embarrassing moment?
    • Are you happy with how you were raised?
    • What quality do you value most in a friend?
    • If you could, would you want to be famous?
    • Have you had any near-death experiences?
    • What’s the most trouble you’ve ever been in?
    • Do you believe in astrology? Why or why not?
    • What’s your relationship to mental health like?
    • Are you closer to your mom or your dad? Why?
    • What’s one thing you’d change about the world?
    • Who in your life deserves the biggest thank you?
    • Do you express your emotions or suppress them?
    • What’s the best compliment you’ve ever received?
    • What’s the most important relationship in your life?
    • What’s the hardest truth you’ve had to face this past year?
    • Who in your life do you wish you could make amends with?
    • What’s one piece of advice you’d give to your younger self?
    • What’s the craziest thing you’ve done for someone you love?
    • What do most people overestimate or underestimate about you?
    • Would you rather be the funniest or smartest person in the room?
    • Would you rather always be stressed and busy, or always be bored?
    • Do you think it’s possible to be “just friends” with someone of another gender?
    • What’s something you’ve tolerated in the past that you no longer have space for?
Section 3 of 6:

Deep Questions to Ask Your Partner

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  1. If you want to feel close to your partner and deepen your connection, ask about their communication style, relationship goals, and overall perspective on love. Matchmaker Erika Kaplan says it’s important to learn about “what you need in a relationship” since “people receive and give love in different ways.”
    • Why do you love me?
    • Do you regret dating anyone?
    • What’s your definition of love?
    • Do you want kids in the future?
    • Why do you think people cheat?
    • How would you define cheating?
    • Have you ever ghosted anybody?
    • Why did your last relationship end?
    • How many people have you dated?
    • What’s your idea of the perfect date?
    • Have you ever cheated on someone?
    • When do you feel closest to me and why?
    • Do you believe in soulmates or twin flames?
    • What do you appreciate the most about me?
    • What do you think you are learning from me?
    • What’s your favorite memory of the two of us?
    • What do your friends and family think about me?
    • What are your non-negotiables in a relationship?
    • What do you fear the most about our relationship?
    • What recent experience made you feel closer to me?
    • Do you prefer physical or non-physical compliments?
    • Do you think physical or emotional cheating is worse?
    • What’s one thing I can do to improve our relationship?
    • Do you think it’s okay to tell white lies in a relationship?
    • What are your green flags in a relationship? Red flags?
    • On a scale of 1-10, how open do you feel I am with you?
    • How much personal space do you need in a relationship?
    • What is the pain in me you wish you could heal and why?
    • What is one experience you wish we never had and why?
    • What’s the biggest challenge in our relationship right now?
    • When’s the last time I hurt you, even if it was unintentionally?
    • If you could relive one day in our relationship, what would it be?
    • What do you think is the key to a happy and healthy relationship?
    • How do you think responsibilities should be divided in a marriage?
    • How long did it take for you to move on from your last relationship?
    • If this was our last conversation, what would you want me to never forget?
    • What’s the biggest lesson you’ve learned from your previous relationships?
    • What was your first impression of me and how has that changed over time?
    • Are there any insecurities from previous relationships that you carried into this one?
    • Would you rather be cheated on and never know, or cheat and have your partner find out?
    • What’s a sacrifice you feel you’ve made that I haven’t acknowledged and why do you think that is?
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Section 4 of 6:

Deep Questions to Ask About Life

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  1. If you’re talking to a colleague or someone you’ve recently met, asking creative yet thought-provoking questions can help you learn more about them (without making things uncomfortable). Some topics you can bring up include their personality, hobbies, interests, and tastes:
    • What brings you joy?
    • Do you have any pets?
    • What’s your spirit animal?
    • What’s your favorite book?
    • What’s on your bucket list?
    • What’s your death row meal?
    • What’s your biggest pet peeve?
    • Do you have any hidden talents?
    • What motivates you to work hard?
    • What’s your best and worst habit?
    • What’s your dream vacation spot?
    • How do you spend your free time?
    • What’s one skill you wish you had?
    • What’s your favorite type of cuisine?
    • What kind of music do you listen to?
    • What’s your most prized possession?
    • Do you prefer staying in or going out?
    • Do you like or dislike surprises? Why?
    • What’s your favorite conspiracy theory?
    • Who are your dream dinner party guests?
    • What fictional character are you most like?
    • What’s something you love learning about?
    • What’s your favorite quality about yourself?
    • What role do you play in your friend group?
    • What’s the scariest thing you’ve ever done?
    • What’s one topic you could write a book on?
    • What’s the best decision you’ve ever made?
    • What’s the biggest misconception about you?
    • What kind of person were you in high school?
    • If you had one wish right now, what would it be?
    • Are you more like your mom or your dad? How so?
    • Do you prefer spending time with friends or family?
    • What’s your most controversial opinion or hot take?
    • How do you like to stay updated on current events?
    • How and why did you choose your current position?
    • If given the opportunity, would you go to Mars and why?
    • If you won the lottery, what’s the first thing you would do?
    • What form of public transportation do you prefer and why?
    • Who’s the first person you would call if you received bad news?
    • If you could put up a statue of someone, who would it be and why?
    • What’s one thing that you do on a daily basis that no one knows you hate doing?
Section 5 of 6:

Deep Questions to Ask About Life

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  1. Everyone has a unique worldview and perspective on life, which often leads to a meaningful conversation. Ask your loved one these philosophical questions to gain greater insight into their mind, and connect with them on a deeper level:
    • Are you afraid to die?
    • When do you feel most alive?
    • Can people ever really change?
    • Do you think about death often?
    • What’s your biggest dream in life?
    • Do you believe in second chances?
    • Where do you see yourself in 5 years?
    • Do you believe in luck, fate, or destiny?
    • Do you think a person can be born evil?
    • What’s your biggest regret in life so far?
    • What do you think is the purpose of life?
    • Do you think money can buy happiness?
    • What do you think happens after you die?
    • What has become clearer to you with age?
    • Do you believe there’s life on other planets?
    • Do you think everyone has a purpose in life?
    • What do you believe in that others might not?
    • Has social media improved or impaired society?
    • What do you want people to say in your eulogy?
    • What’s the biggest lesson you’ve learned in life?
    • Would you rather have more time or more money?
    • What core values guide your actions and decisions?
    • How do you handle life’s challenges and uncertainties?
    • Would you rather save 100 strangers or one loved one?
    • Is it important to forgive people who have wronged you?
    • Do you believe there’s anything worth killing or dying for?
    • Would you rather find true love or win 100 million dollars?
    • What event in your life has shaped you most as a person?
    • Do you have an easy or difficult time letting go of the past?
    • If you only had one day left to live, how would you spend it?
    • What’s one thing you would do if you knew you could not fail?
    • If you could only love or be loved, which one would you choose?
    • What’s something you’re choosing to ignore in your life right now?
    • Would you rather be able to look into the future or change the past?
    • Do you have a personal philosophy that shapes your outlook on life?
    • If you could solve any world problem, which one would it be and why?
    • Would you rather know the cause of your death or the date of your death?
    • Of all the people you’ve lost, which death shook you the hardest and why?
    • If you could go back and change one decision in your life, what would it be?
    • If you had to relive the same day over and over, which day would it be and why?
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Section 6 of 6:

How to Ask Deep Questions & Connect with Others

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  1. Practice active listening . When it comes to deepening your connection with someone, it’s important to give them your undivided attention during conversation. Put your phone away, maintain eye contact when they speak, and follow up with an engaging question to make them feel valued. According to certified leadership and life coach Christina Stathopoulos, PCC, ACCC, you should “really listen to what they’re saying,” instead of “planning what you want to say next.”
  2. People are more likely to open up to you when they feel safe and secure, so keep an open mind when you talk to them and express interest in their responses. Remember, everyone has different experiences and viewpoints, and approaching the conversation with an open heart can help foster a warm, meaningful exchange. [2]
  3. If you want to strengthen the bond in your relationship , you need to ask meaningful questions—and prepare to do the same! You can’t expect someone to open up if you’re not willing to reciprocate, so make sure to participate in the conversation and provide more personal information about yourself.
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      Tips

      • Before asking deep questions, you might want to discuss what topics are off-limits, such as personal traumas, past relationships, or family dynamics. If the other person doesn’t feel comfortable with a question, respect their boundaries and move on.
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      References

      1. ↑ https://www.betterhelp.com/advice/relations/25-questions-to-get-to-know-someone-deeply/
      2. ↑ https://www.calm.com/blog/questions-to-ask-to-get-to-know-someone

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