Deep conversation topics should be a thing taught in school, because…
It’s almost inevitable — you spend a lot of time in your daily life talking about surface-level, mundane things.
And we all know:
From the latest gossip at work, to being lost in generally polite conversation topics with strangers at a bar, to re-visiting the same social media posts with friends, it can become rather boring to just be keeping up with whatever is expected of you in a conversation.
Why is this, though? Because as a strong, motivated man, you crave depth in your conversations — you know that there’s more that lies beneath the surface of every person, and have a genuine desire to find the right questions to ask to lead the conversation in a more fulfilling direction.
We’ve put together a list of our favorite types of deep questions to ask, so that you can get started with, or enhance your repertoire of ways to break through the monotony of everyday conversation and really start learning what it is that makes people who they are.
Take a look through the following areas of deep conversation topics, and commit a few of them to memory to be prepared for wherever your conversations might lead you throughout the day.
Let’s say there’s someone you want to start a conversation with, but they seem to be a little heady for you. They’re big readers or intellectuals, and you don’t want to come off vapid, right?
Try a few of these next time to set a deep and thoughtful tone to your conversation with deep and thoughtful people.
Here are 16 deep conversation starting topics:
1. What do you do to impress others deliberately?
You’re asking for self-reflection and sincerity here.
2. What will you never do?
Find out what lines a person draws and how that defines them.
3. What’s an uncommon belief you hold?
This answer could be anything and lead anywhere, but it’s sure to have a lot of depth.
4. What does your joy look like today?
“Joy” is such a personal and powerful term. It’s deeper than happiness and far more personal.
5. Would you rather have less work or more work that you enjoy doing?
What is the point of work? And should we find it enriching or just get it over with?
6. What is important enough to go to war over?
It’s an ugly and heavy responsibility, but what is really worth fighting for, if anything?
7. What does ‘The American Dream’ mean to you?
Another complex topic, and this one has such a personal side to it.
8. If you could instill one piece of advice in a newborn baby’s mind, what advice would you give?
You’re asking them to condense all their wisdom to one simple point.
9. Are you more worried about doing things right, or doing the right things?
A question of ethics without an easy answer.
10. What do you do over and over again that you hate doing?
Another chance for self-reflection, and to discuss flaws and how to overcome them.
11. What do you understand today about your life that you did not understand a year ago?
Give them a chance to discuss personal growth on a deep and meaningful level.
12. What makes you uncomfortable?
A chance for a little confession, and the answers may shock you.
13. What one ‘need’ and one ‘want’ will you strive to achieve in the next twelve months?
A great, goal-oriented question to see where this person sees themselves in the near future.
14. What will you never give up on?
It could be an ideal, a person, or a sports team, but it’s sure to have deep meaning to them.
15. When you look into the past, what do you miss the most?
Nostalgia is one of our most powerful, and deepest, emotions.
16. What’s the best part of being you?
Define yourself, then feel pride in yourself. A great way to get people in a good mood to be deep.
Having a few of the best deep conversation topics, and deep questions to ask stored in your memory is a great way to breathe new life into a conversation. Use these when you’re not entirely sure where to take the conversation, but want to open up a dialogue that can go deeper with whomever you’re speaking to.
Here are the top 3 conversation topics:
Every person will face a unique series of challenges in their life — and their responses to these challenges will shape them as a person. If you know the challenges that you’re facing, you can prepare better for them, and speak more honestly about what it is that you want out of your life.
Learn more about your conversation partner’s challenges with these challenge-topic questions:
17. What is your biggest day-to-day challenge?
Every day is a new opportunity to learn and grow, but you can only do this if you’re aware of what challenges you.
18. Do you find your work challenging and interesting?
Challenging work can be a fantastic catalyst for personal growth.
19. How often do you set goals for yourself?
Having something to work towards keeps a person motivated, and setting goals keeps you on track.
20. What kind of goals do you have for the next year?
Looking towards the future can put the present into perspective.
21. When have you given up on something?
Or, more importantly, was it justified? Sometimes we have to let things go and move onto the next challenge.
You purpose in life — and your own understanding of what that might be — can be a great source of inspiration and inner strength. For the person with a clear purpose, it’s an amazing chance to share that with someone else; for the person without such a clear sense, talking about these things can help to clarify what it is that they are meant to be doing.
Here are a few ‘purpose’ based conversation questions:
22. Where do you find purpose in your life?
Whether job, family, or hobbies, a person’s priorities say a lot about their sense of purpose.
23. Do you find purpose in your work?
About a third of anyone’s life is spent at work; is it worthwhile?
24. If you won the lottery, would you keep working in your current profession?
Is the work they’re doing important for more than just money?
25. Do you think people have a “higher calling” in life?
If so, how do you go about finding that purpose and honoring it?
26. What have you been most proud of learning lately?
If you stop learning, you stop growing; people who learn more find more purpose in life.
Family and Friends
Family, be they through blood or through mutual experiences, are your support system; when the rest of life starts bearing down on you, your ability to turn to loved ones can make all the difference. Everybody has memories of their family and friends that go much deeper than day-to-day activities.
Open up a deeper conversation about family and friends with questions like these:
27. Who do you consider as family?
Family isn’t only by blood relation, after all.
28. What role does family play in your life?
What sort of relationship do they have with their family?
29. What is your best friend like?
The people you spend the most time around have a huge influence on you — even more so with your best friend.
30. How did you meet your best friend?
The moment you meet someone important to you marks a big phase in your life, with deep implications for your future.
31. How much time do you spend with your family?
And what sort of influence does that have on you?
When general deep questions can seem a bit too formal, move towards something more interesting. These questions cover interesting conversation topics that just about anyone can get interested in, as they apply equally across the whole range of human experience.
Here are 15 deep, yet super interesting conversation topics:
Culture is such an interesting topic, because it’s hard to pin down to any one definition — you can have a whole slew of interesting conversation topics that cover a wide range of preferences, and open up the conversation to new input.
Explore culture with your conversation partner with questions like these:
32. What role does music play in culture?
People have been fascinated with music since before recorded history, and music is said to “speak to the soul“.
33. Does language affect how we see the world?
Bonus question: Do you speak more than one language?
34. Do you think you could live in another country?
Interesting on its own, this is also indirectly asking, “how well do you deal with big changes?”
35. Which world culture is the most fascinating to you?
Each unique culture has elements that resonate with certain people on a deeper level.
36. Do you believe the way we dress affects how we think?
Everyone who pays attention to their daily experiences can weigh in on the topic of human nature — making it an ideal go-to topic if you’re not sure what the person you’re talking to is interested in. If you’re interested in human nature, you’re interested in life itself, which might be the deepest conversation topic of all.
Lead into some of the deepest conversation topics in life with some of the following:
37. Are people defined by the culture they grew up in?
The classic “nature versus nurture” argument, this one questions what is most deeply ingrained in you.
38. Are people better at creating things, or destroying things?
A person’s view on this reveals an optimistic or pessimistic attitude, which will affect their whole life.
39. If you had to sum up human nature in 3 words, which would you choose?
Simple answers can often provoke deeper thought than long, complex ones.
40. Which is more important: The human body, or the human mind?
Placing importance on intellect or physicality can definitely change a person. Where is your deepest connection to yourself?
41. Why do people do things which they know are bad?
Or, what is the line between “good” and “bad” in the first place?
Thinking about how our lives may continue to grow, and what we might experience in the future, is a uniquely human trait. Talking about the future with someone shows you where their attention is at, by giving insight into what they see coming of their life in the near or distant future.
Look towards the future with questions like the following:
42. Do you think the future will be brighter or darker than today?
Another way of asking the old “glass half full/half empty” question, which shows a person’s deepest attitudes towards life.
43. What role do humans play in shaping the future?
How much do our choices matter for what we’re likely to experience soon?
44. Do you think we’ll colonize another planet? Would that be a good thing?
If it’s necessary to find a way to live on another planet, what does that say about life on Earth?
45. What will be most important to you in 10 years?
As we learn and grow, our priorities change; is your future something that you look forward to?
46. Will the next generation be in a better or worse position than ours?
If better, why? And if worse, what can we do about it?
If you’re looking for questions to get to know a girl better, certain topics carry a lot more weight than general superficial or deep questions. Memorize a few of these deep questions to ask a girl, in each category, and you’ll be ready to make a stronger connection when the opportunity arises.
The roles we play, and how well we play them, determine a lot about how we experience the world around us. Lots of girls (and guys) today aren’t comfortable with the roles that they feel they’ve been forced into, and really appreciate the opportunity to talk about what it is they actually want to be doing with their lives.
Have an honest, deep conversation about roles by starting with some of these questions:
47. How do our roles define us in society?
Everyone plays different roles throughout their lives. What do theirs mean about who they are?
48. Are our roles defined for us, or do we define them?
Or, how much do we contribute to defining ourselves as people?
49. If you could choose to be anything, what would you be?
This one isn’t limited only to career options, but for how a person would want to be in a moral sense, too.
50. How does our role in life affect how other people see us?
The way others perceive us creates both new limitations and new opportunities.
51. Are you comfortable with the role(s) you play in life?
Because really, just because a person is good at a role doesn’t mean it’s the right one for them.
Love and Loss
With how fast the modern world seems to be moving, you’re more likely to experience love and loss over and over again in your life than any generation that has come before. The people you love, and the people you lose, contribute so much to how you view life — which makes it one of my favorite topics for deep questions to ask a girl.
Find what love and loss mean to the girl you’re speaking to with the following questions:
52. Is it better to have loved and lost, than to have never loved before?
The British poet Alfred Lord Tennyson penned this classic. It quickly tells you what they think about love/past love.
53. How important is it to you to be in love?
And as a follow up, what does it mean to you to be in love? A person must love themselves before loving others.
54. Have you ever lost something important to you?
We all must learn to deal with loss in our own ways; getting to the core of our ability to cope with loss is a necessary part of growing up.
55. Can you have love without having loss?
Realistically, the two are opposite sides of the same coin — but this understanding can only be reached through a deep connection with your own experiences.
56. What does it really mean to love someone?
This will be different for different types of love (familial, romantic, friendly, etc.).
Almost everything you do in life can be measured against how it affects your happiness, because happiness is so often what makes the experience of life seem worthwhile. The things that affect a girl’s happiness will affect her entire life, making it a great segue into other deep conversation topics.
Look at the bright side of deep questions with inquires like these:
57. What makes you smile in the morning?
Because each day is a chance at something new and beautiful.
58. How important is happiness to you?
Valuing your own happiness, and the happiness of others, is a hard-earned lesson that stays deep within a person.
59. Does your job bring you happiness?
With the amount of time we spend in our jobs, they should contribute to a better life. Does theirs?
60. Are you happy with your current experience of life?
And if not, what are you doing to change that?
61. What do you do to make other people happy?
Happiness is best, and deepest, when shared with others.
Whether you’ve been in a relationship for six days, six months, or six years, there’s always room to know each other more deeply. Asking good questions for couples, that have to do with both of you is a sure way to open the door for further conversations about how you want to choose to live your life together.
Here are 2 great conversation starters for couples:
For any sort of relationship, but especially for couples, having goals that you can work towards together goes a long ways towards making your relationship worthwhile. By planning together for the future, it can make even the most mundane, everyday tasks seem important for how they contribute to your goals.
Get yourselves on the same page with goal-setting questions like the following:
62. Where would you like to be living in 5 years’ time?
Where a couple chooses to live can make a huge difference in how deeply they are able to connect.
63. How often would you like to be traveling?
Seeing the world is an amazing way of getting to know someone on a deeper level.
64. What goals do you have in your job right now?
And are your goals compatible with each others’?
65. Where do you see our relationship at this time next year?
Being committed to a life together requires a depth of feeling of hope, optimism, and planning.
66. What’s your biggest goal in life right now?
And the kicker: How can you help each other with that?
In a relationship, you share things with your partner that you might not with anybody else around you. The topic of “fears” is perfect for deep questions to ask your girlfriend, because she’s more comfortable sharing these intimate details with you than with her casual friends.
Share some of your most intimate experiences with some of these questions:
67. What’s an irrational fear that you have?
We definitely don’t always understand our own fears, but being able to question them helps to understand them on a deeper level.
68. Do you worry about your work?
If so, what is the root cause of this? This one prompts deeper thought into something often ignored.
69. What do you fear for in the future?
Making a plan to assuage those fears can be a powerful form of relief.
70. How do you deal with things that scare you?
Knowing your partner’s coping mechanisms lets you learn to support them better in hard times.
71. Which is more important: Fear, or hope?
Having a balance between the two keeps us level and healthy in life.
Some conversations go in one ear and out the other. Others make an impression that lasts forever. These thought provoking questions encourage the latter.
Coming up with new topics to talk about is no easy task, especially with people you already know well. Use these topics to invigorate the mind and challenge the status quo.
These topics are guidelines, but the possibilities are endless. Use them to start conversations that can go in any direction.
Before you start a discussion with these deep topics, think about your responses. You don’t want to start a conversation and have nothing to contribute. At the same time, let the conversation flow and follow its own course. Spontaneity is the lifeblood of a memorable dialogue.
Here are 7 of the best deep and thought provoking conversation topics:
72. They say you learn something new every day. What did you learn yesterday?
And if you can’t remember what you learned, did you really learn it?
73. Why can humans create and other beings cannot?
And the answer isn’t just opposable thumbs.
74. Do you view others as supporting characters in your story, or main characters in their story?
Is it solipsistic in here, or is that just me?
75. What actions would you take to earn a loved one’s trust back, after you have broken it?
And at what point is a relationship beyond repair?
76. If you had to be filled with one food ingredient what would it be?
Water doesn’t count.
77. Security or freedom?
Can you have both?
78. What makes words what they are?
The evolution of language is a strange and complex thing. Try to create your own words and assign them meaning.
Downloadable List of Deep Conversation Topics
Looking for More Deep Conversation Topics?
This roundup gets you started with a broad range of topics for deep questions with a variety of people — but if you’re looking for something more specific,
We got you covered:
- Looking for something more intellectual? Philosophical questions are the way to go.
- You have to begin with great conversation starters before moving to the deepest questions.
- Got questions about the meaning of life, the universe, and everything? Sounds like you’re going to want some existential questions to ask.
Deep conversation topics can make the difference between having another boring chat with a stranger and really getting to know someone better — but you have to know the right questions to ask.
Choosing conversation topics to satisfy a broad range of interests is a great start that will give you the best deep questions to ask to really make connections with people.