But talking about the same things over and over again can get boring. Perhaps you’d want to try asking deep and meaningful questions for a change.
If you’re thinking right now, “what kind of questions should I ask then?”. Here’re 100 possible deep questions to ask for more meaningful conversations.
Questions about who they are
These conversation starters revolve around their life and experiences, including the past and present. Asking deep meaningful questions about their life invites new insights into your friendship.
- What’s your favorite memory from your childhood? What’s the worst?
- How do you spend your free time?
- What’s your guilty pleasure?
- What’s your preferred genre of music? And Why?
- What’s your choice of poison? (“poison” refers to alcoholic drinks)
- Do you like and play any sports? Why?
- What is the best thing you’ve ever eaten? What’s the worst?
- What’s your favorite movie? Why?
- If you were to get a tattoo, what kind would you want?
- What was the last book you read? How did you feel about it?
- Do you have any pet peeves? Why?
- What’s your favorite app? And why?
- What’s the best thing that has ever happened in your life?
- If you could have any superpower, what would it be? And why?
- What’s your dream vacation?
- What’s your favorite cuisine?
- Do you have a daily routine? What’s your favorite part of it?
- What do you do when you’re stressed?
- How would you describe the “perfect meal”?
- What is your best moment growing up?
Questions about their work/careers
Plans about the future, their current career, or goals are an incredibly important aspect of everyone’s lives. So there’s nothing wrong with asking deep questions in fear of things turning awkward. What’s important is that you should also be ready to answer the same questions or/and build conversations from their answers.
- What is your dream job?
- What job would you never do?
- What annoys you the most about your career/field of study?
- In ten years, do you see yourself in your current job/field of study?
- What made you interested in pursuing this career/field of study?
- Where do you think your career is going?
- What’s the best memory you have in your career?
- Do you have any goals in life, besides your career?
- What is your best memory so far in your job/internship?
- What was your first internship like?
- Was there anything holding you back from your chosen career?
- Ten years ago, would this be your dream job?
- What does an average day at work look like for you?
- Do you like working from home or spending the day in the office/ at school?
- What’s been the most challenging experience you’ve had at school/work?
- Do you wish you were earning more in your career?
- Do you have any regrets about your career/field of study?
- How are you balancing between free time and work/school?
- What gets you through a day at work/school?
- Is there anything in your resume that isn’t true?
Questions about connections
These questions refer to the relationship with friends, partners, and family. Deep questions on relationships with your friends can reveal aspects of your friendship unbeknownst to both of you and open up conversations about their thoughts on their relationships and marriage. While discussing familial relationships with your parents or siblings is sure to bring a whole new perspective to the table.
- What do you do when you have a crush?
- When was your first relationship?
- What do you love most in a relationship?
- What’s your “ideal” first date?
- How long does it take until you decide you’re ready for marriage?
- Do you think it’s hard making meaningful friendships?
- What’s the most important thing you find in a friend? And in a partner?
- Do you have any deal-breakers when meeting new people?
- Do you find it hard to trust someone?
- What do you do when you have a fight with your partner? Friend? Family members?
- Is there anything you want to work on to be a good partner?
- How did your parents show love and affection to you?
- Are you close to your parents or siblings? If not, why?
- Do you have a favorite in your family?
- What’s the best memory you have with your family? The worst?
- If you could change anything about your family, what would it be?
- Do you think growing up with your family affected your future relationships?
- What was it like growing up in your family?
- What would you tell your younger self about growing up with your family?
- Do you want to have your own family? Why?
Questions about values
These questions refer to a person’s ethics and moral values. This isn’t meant to be controversial as it is a core aspect of one’s personality. Therefore, it’s important to start meaningful conversations about this with the people who matter. Doing so with an open mind fosters trust and builds stronger connections.
- If you were to die tomorrow, what would you want your last memory to be?
- If you were omnipotent for a day, what would you do?
- What values have you learned from your parents? Relationships? Career?
- Have you ever made a life-altering decision? What was it?
- When do you think a person’s ready to open up to someone?
- Do you believe in true love?
- What do you believe is your purpose in life?
- What is your biggest fear?
- Do you value money over well-being?
- Do you believe your zodiac/horoscope sign perfectly represents who you are?
- Do you think you can be easily influenced?
- What are some ethical dilemmas you’ve encountered?
- Would you rather die happily young, or grow old with regret?
- What do you see as “success”?
- Who would you prioritize first: friends, partner, or family?
- What do you do when faced with tough decisions?
- Do you believe in life after death?
- In a life or death situation, would you save a friend over five strangers? (“The Trolley Problem”)
- Do you think lying is “always” wrong?
- Would you risk your life to save another?
Questions about topical content
These questions refer to important events and topics that are around us every day. Think meaningful conversations about social media, the latest news, technology, and current affairs.
- Do you think social media affects us more than it should?
- What are your app rankings: Instagram, Facebook, Twitter, etc.?
- How do you feel about the public education system?
- What do you think are the reasons for a decline in Unemployment?
- What is your opinion on drug consumption?
- Are there any current events that are affecting you? Your friends? Family? Career?
- Do you trust the information you see on social media platforms?
- What are your thoughts on racial issues and discrimination in [Country]?
- What do you think of cancel culture?
- In 10 years, where do you see [Country]?
- Do you like politics? Why or why not?
- Is gender identity environmental or biological?
- Do you stay up to date with current events?
- What does it mean to be environmentally friendly?
- Do you “act” differently online versus offline?
- What do you think of “anti-vaxxers”?
- What are the three most important issues facing this world right now?
- What do you think is the best thing about social media? The worst?
- Do you think social media can affect political views?
- Do you think social media has made real-life boring?
Meaningful questions brings better connections
Whatever situation we’re in with friends or family where the conversation has turned stale, these meaningful questions are meant to liven up the mood and make for an optimistic and interesting day. They’re simple questions that can lead to deeper conversations that reveal new things about the people who matter.
If you’re interested in similar topics on friendships and connections, check out our article on the science behind why you vibe with certain people by one of our talented writers.
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