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279 Deep Conversation Starters To Help You Really Get To Know Someone
mbg Spirituality & Relationships Editor
By Sarah Regan
mbg Spirituality & Relationships Editor
Sarah Regan is a Spirituality & Relationships Editor, and a registered yoga instructor. She received her bachelor's in broadcasting and mass communication from SUNY Oswego, and lives in Buffalo, New York.
Connecting and bonding with other people is one of life's most fundamental pleasures—but it takes more than small talk to get you there. Whether your first date is hitting a lull, you want to spark some stimulating conversation, or you're trying to get to know someone on a deeper level, here are over 270 deep conversation starters to try.
Deep conversation starters about life
- What are you passionate about?
- Is there anything you're worried about?
- How connected are you feeling to the world?
- What consistently brings you joy?
- What feels hard in your life right now?
- What's bringing you pleasure right now?
- What's something difficult you're working on?
- Where are you finding the most meaning in life?
- What do you feel has been the most important thing you've done in life so far?
- What lasting impact do you know you've made in the world?
- What's the most important quality a person can have?
- What is the meaning of happiness?
- Do you place a bigger value on helping yourself, your family, or the world? How so?
- Is there a motto or principle you live by?
- s it better to be realistic or optimistic?
- Are you a city person or a country person?
- What element do you resonate most with: fire, water, earth, or air?
- Are you a risk-taker?
- Do you have any routines that you stick to religiously?
- Have you had any major turning points in your life so far?
- What's something you're proud of?
- Do you have any beliefs or values that have changed over the years?
- What role would you play in the group of people trying to survive a zombie apocalypse?
- Are you a good gift-giver?
- What's the best gift you've ever received?
- Have you ever done anything illegal?
- What's your favorite part of your typical day?
- What does self-care look like for you?
- What's a question you wish more people asked you?
- What does your ideal day look like?
- What's something random that you're extremely into?
- What's your astrology sign, and do you think it's accurate?
- What's the most interesting thing you've read recently?
- Do you feel like you've found your life purpose?
- What is your greatest fear?
- When did you last cry in front of another person?
- When is the last time you felt truly, exuberantly happy?
- If money wasn't an issue, how would you spend your days?
- Do you love yourself?
- How do you feel about your gender?
- What feels hard in your life right now?
- When do you feel most alive?
- What is the meaning of life?
- How do you like to celebrate your birthday?
- Cat person or dog person and why?
- What's your worst habit?
- What's your best habit?
- Have you ever been to therapy?
- What's your relationship to religion?
- Are you a spiritual person?
- Best concert you've ever been to?
- Worst concert you've ever been to?
- What’s something you think I could learn from you?
- How do you calm yourself down when you're feeling stressed?
- When is the last time you felt deeply inspired, and why?
- Who's an older person in your life that you really look up to?
- If you could wake up with any skill tomorrow, what would you choose?
- Do you identify as an introvert, extrovert, or ambivert?
- What's one thing you love about being in your (30s/40s/50s/etc.)?
- What are five things you couldn't live without?
- What do you think happens when we die?
- What does happiness mean to you?
Deep conversation starters about growing up
- What were you like as a child?
- What were you like as a teenager?
- What were you like in college, if you went?
- Are you close with your family?
- Do you think your family knows the real you?
- What is your relationship with your parents like?
- Has it always been that way?
- What was your childhood like?
- Would you change anything about the way you grew up?
- Do you feel like money affected the way you grew up? How so?
- Do you feel like race has affected your life? How so?
- What do you think your younger self would think about who you are today?
- Is there anything from your past that you're ashamed about?
- In what ways do you think you have grown as a person?
- What is the most difficult thing you've ever had to go through?
- Do you want to be more or less like your parents?
- Were you raised under a certain religion?
- How have your parents affected the way you show up in relationships?
- Are you close with your siblings?
- Did you have a favorite pet growing up? What made them your favorite?
- In what ways do you still feel like a kid inside?
- Do you feel connected to your inner child?
- What’s something your parents have taught you about love that you now realize is wrong?
- What qualities do you admire most in your parents?
- What's one of your most cherished memories?
- What's something you used to believe in that you don't anymore, and what changed?
- What were your grandparents like?
- Do you like your extended family?
- What word would you use to describe your family?
- Which family traditions have you carried on?
- Tell me about a time you did something you "weren't supposed to" but it was worth it.
- Any traditions you were happy to say goodbye to?
- What's one thing the family probably doesn't know about you?
- What's one thing you wish you could tell your younger self?
- What people have made you who you are today?
- What experiences have made you who you are today?
- What's one dish or meal that reminds you of home?
- Which scents do you associate with childhood?
Deep conversation starters about love & relationships
- Why do you think you are the way you are in relationships?
- What does an ideal relationship look like to you?
- What do you think about the concept of marriage?
- What does commitment mean to you?
- What do you think you would be like as a parent?
- Do you want children at all?
- What scares you about becoming a parent?
- What do you value most in a friend?
- When is the right time to say "I love you" to someone?
- What little things make you feel loved in relationships?
- Do you enjoy compliments?
- Do you believe in soul mates?
- How about twin flames?
- When was your first kiss?
- What kind of proposal would you want?
- What's your favorite thing about our relationship?
- What makes you feel beautiful?
- Is jealousy healthy in a relationship?
- Is lying ever OK?
- Is cheating ever OK?
- Do you talk about your feelings often? Why or why not?
- Who do you feel most comfortable talking about your feelings with in your life?
- Who do you feel least comfortable talking about your feelings with?
- What are your thoughts on pornography?
- What does friendship mean to you?
- How would you feel if your partner made more money than you?
- What was your last relationship like?
- What's your usual approach to conflict?
- Morning sex or sex at night?
- How long does it take you to open up to someone?
- What's your attachment style?
- What are your preferred love languages?
- What would a perfect date night look like for you?
- What was your last big fight about?
- Why did your last relationship end?
- Have you ever been in love?
- Which relationship was your most regrettable? Why?
- What are the biggest relationship lessons you've learned?
- Are you sexually fulfilled?
- How do you define unconditional love?
- Is there anything you consider unforgivable, if so what is it?
- Have you ever hurt someone and deeply regretted it? Did you ever make amends?
- What are your relationship deal-breakers?
- Have you ever broken up with a friend?
- What does it mean to be a good partner?
Deep conversation starters about today's world
- What does the world need more of?
- What does the world need less of?
- Do you think organized religion have a bigger or smaller place in society going forward?
- Do you feel like the world is changing for the better or changing for the worse? How so?
- What from the past is worth preserving?
- In what ways has society changed during your lifetime? What do you think caused these changes?
- What's your latest controversial hot take?
- Do you think humans are inherently good or inherently evil?
- Who is a public figure (musician, artist, politician, etc.) you love that you think other people don't get?
- What's more important: science or art?
- What does masculinity or being a man mean to you?
- What does femininity or being a woman mean to you?
- What gender stereotype do you wish the world would let go of?
- What's a conspiracy theory you actually believe?
- What reality TV show would you be on?
- Thoughts on reality TV?
- Is there a cause you care about for which you would be willing to risk your life?
- Do you enjoy discussing politics?
- What are your main political views?
- Do you vote? Why or why not?
Deep conversation starters about the future
- What are you excited about right now?
- Is there a decision you're contemplating that would be helpful to talk through together?
- What do you imagine your legacy will be?
- How long do you think you'll be remembered?
- Where is the next place you'd like to travel?
- What do you want to do in retirement?
- What is one part of yourself that you think still needs work?
- What changes would you like to see in the world during your lifetime?
- How do you want to impact the future?
- What are your dreams for your future?
- What would you want your eulogy to say?
- What scares you about the future?
- What is your main focus in life going forward?
- What do you think your family will look like in 50 years?
FAQs:
What are some deep convo starters?
Some deep convo starters include asking about things like their purpose, their childhood, their feelings about certain topics, etc. (i.e. "What was your childhood like?" or "What do you think is the meaning of life?")
How do you trigger a deep conversation?
In order to trigger a deep conversation, the ball is in your court to initiate the depth. By opening up and getting vulnerable, and then asking a deep question or broaching a deeper topic, people will feel more comfortable getting deep with you.
How do you start a deep text conversation?
If you want to start a deep text conversation, introduce the topic you're interested in talking about, offering a bit on your take. Then, ask for their thoughts.
What are some fun questions for deep conversations?
Some fun questions for deep conversations include asking what brings them the most joy, what their ideal day would look like, or what their dream job would be.
The takeaway
Small talk can only get you so far if you really want to get to know a person—so skip all that and jump right into the hard-hitting questions. With a touch of your own openness and vulnerability, and a handful of solid conversation starters that spark connection and depth, you can learn something new about anyone.
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