72 Very Deep Questions To Ask a Friend or Someone You Want to Get to Know
Want to connect on a deeper level? These deep questions to ask a friend or someone new reveal who they really are, beneath the small talk.
Deep questions to ask a friend or someone you’re getting to know deeply can completely transform your relationship. The right ones bring you closer, build emotional trust, and reveal who someone really is, beyond the filters, the rehearsed stories, or the flirty banter.
In fact, research from the University of Kansas found that just one quality conversation a day with a friend can boost your mood and well-being dramatically.
📚 Source: Hall, J.A., 2023, One quality conversation can boost daily well-being
Psychologists call this the self-disclosure effect, when we ask and answer meaningful questions, we fast-track intimacy and emotional safety. That’s why we’ve carefully curated these deep questions: to help you skip the small talk and build real connection with a friend, a crush, or someone you’d like to know better.
5 powerful deep questions to ask someone right now:
- What’s one memory that shaped who you are today?
- When do you feel most like yourself?
- What’s something you wish more people understood about you?
- If you could instantly master a skill, what would it be, and why?
- What do you value more: comfort or growth?
Whether you’re deepening a friendship, exploring a new bond, or figuring out if you and someone are emotionally aligned, the questions we’ve shared here are designed to open hearts and spark the kind of conversation you’ll remember for years.
Deep Questions to Ask Friends or Someone You Want to Get to Know
Now, there are different kinds of questions you need to ask people depending on their relationship with you. If you’re looking to ask deep questions to someone you’re bonding with, or someone you see as a potential life partner, read on.
But if you’re looking for other specific relationships, we have the best deep questions for all of them. Just click on any of the links below, and jump straight to the set of life changing, deep questions for the right person.
👉 Looking for flirty questions? Start here:
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Deep Questions to Ask Someone You’re Just Getting to Know
These are perfect for those early stages, whether it’s a new friend you vibe with, a classmate you’re curious about, or someone you’re lightly crushing on. They’re open-ended, personal without being too intrusive, and offer a sneak peek into who someone really is, underneath the “I’m good, how about you?” default replies.
1. What’s your favorite way to spend a free weekend?
How someone uses their downtime says a lot about what they value, rest, adventure, connection, or creativity. Plus, this gives you instant ideas for shared experiences, without sounding too forward.
2. What’s something you’ve been obsessed with lately?
Whether it’s a niche TV show, a historical event, or making banana bread every week, obsessions are windows into someone’s passions. It also gives you a shortcut to shared excitement.
3. If you had to give a TED talk on something you’re not an expert in, what would it be?
This question invites them to nerd out freely, without pressure to sound smart. You’ll see what excites them, even if they’re wildly underqualified, and that’s often more telling than their résumé.
4. When do you feel most like you?
It’s subtle, but powerful. It invites them to share their most authentic self, the version of them that feels free, seen, and safe. [Read: 34 Qualities of a Good Person & BIG Benefits of Being a Nice Human Being]
5. What’s one thing you wish people asked you more about?
Most people carry around stories or interests they rarely get to share. This question offers them the mic and shows you’re someone who genuinely wants to know them.
6. What’s a random opinion you’ll always defend, no matter what?
Pineapple on pizza? Sitting in the aisle seat on flights? This kind of low-stakes hill-to-die-on adds charm and helps you learn their personality in a playful way.
7. What do you think people misunderstand about you?
This allows for thoughtful self-awareness, or surprising vulnerability. You may discover a softness or strength they don’t usually show on the surface.
8. What’s a small thing in your day that makes you ridiculously happy every time?
Happiness often hides in the little things, a good cup of coffee, an inside joke, a great playlist. This question reveals what lights them up without going too deep.
9. Do you think you’re more introverted, extroverted, or somewhere in between?
Beyond just labels, this helps you understand their energy patterns, how they recharge, how they socialize, and what makes them feel at ease.
10. What would you do if you had one day with zero responsibilities and no phone?
This one’s about freedom, who they are when the world isn’t demanding anything from them. It’s equal parts escapism and authenticity.
11. What’s one value or belief you hope people see in you, without you having to say it?
It’s an elegant way to ask, “What kind of person are you really?” without sounding confrontational. Plus, it often reveals their core motivation in relationships. [Read: What to Look For in a Relationship: 23 Traits of a Happy Romance]
12. Do you believe everything happens for a reason?
This isn’t just about fate, it’s a lens into how they process life, loss, and growth. Whether they’re spiritual, skeptical, or somewhere in the middle, their answer says a lot.
Deep Questions to Ask a Close Friend
So you’ve been friends for a while, you’ve survived some chaotic group chats together, maybe shared fries, trauma, and a few regrettable karaoke nights.
But even close friendships can stay surface-level if you never stop to ask the meaningful stuff. These questions dig deeper into who your friend is, how they see the world, and what truly shapes them. Some might make you both laugh. Others? You might cry. All of them bring you closer.
1. What do you think I admire most about you?
This one flips the perspective and shows how self-aware they are about how others see them. Plus, it’s a subtle compliment built into a question, win-win.
2. What’s a memory of us that always makes you smile?
Nostalgia deepens connection. This one reinforces positive shared experiences and reminds both of you why the friendship matters.
3. Is there a moment in our friendship when you felt especially supported or understood?
This helps you learn how you’ve shown up for them in the past, and how to keep doing it better.
4. What’s something you’ve never told me, but always wanted to?
Yeah, this one’s bold. But if there’s trust, it opens the door for vulnerability, and maybe even healing.
5. What part of your personality do you think is most misunderstood by people?
Friends can still miss things. This question invites a richer understanding of who they are beneath the social masks. [Read: 19 Secrets to Open Up to Someone You’re Dating Even If You’re Scared]
6. If I needed to hear some tough love, would you tell me, or sugarcoat it?
A great way to understand their communication style and how they handle honesty in difficult moments.
7. What’s one fear or insecurity you’ve worked hard to overcome?
A thoughtful way to acknowledge growth and resilience, and open space for deeper emotional connection.
8. Do you believe we’ve helped each other grow, and if so, how?
Let them reflect on the impact this friendship has had. Growth-based reflection adds depth to even the most fun-loving friendships.
9. When do you feel most seen in our friendship?
This helps uncover the specific ways they feel valued, so you can be even more intentional about showing up for them.
10. What does being a “good friend” mean to you?
A classic question, but the answers can be surprisingly nuanced. And it’s a great check-in for how you both define loyalty, presence, and love. [Read: How to Be a Good Friend: 49 Traits & Friend Codes that Define a Real Pal]
11. Have I ever hurt your feelings without realizing it?
This one’s brave, and potentially game-changing. If your friendship has hit a few bumps, this opens the door to clear the air and reconnect.
12. What’s something you admire in others that you’re still working on in yourself?
It sparks humility, reflection, and probably a few laughs if they admit they’re still trying to drink more water or avoid toxic situations.
👉 Looking for naughty questions to tease someone? Check these out!
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Deep Questions To Ask Friends About Personal Growth & Self-Reflection
Whether you’re sitting across from a longtime friend or on hour five of a conversation with someone new who just “gets you,” these deep questions uncover how a person sees themselves, past, present, and future.
We’re talking regrets, turning points, inner work, and those invisible threads that tie someone’s story together. These are the questions that build not just closeness, but mutual respect and emotional clarity.
1. What’s one moment in your life that changed you forever?
Not all life-changing moments are dramatic. Sometimes it’s a breakup, other times it’s a random bus ride. Either way, this question gives insight into what shaped them, and how.
2. What’s something you’ve unlearned recently?
Growth isn’t just learning new things, it’s questioning old beliefs. This reveals humility and how open they are to changing their perspective.
3. When was the last time you felt deeply proud of yourself, and why?
This one’s about self-worth. And hearing someone talk about what makes them proud tells you a lot about their values, struggles, and inner voice.
4. What’s a part of yourself you’re actively working on right now?
Therapy or no therapy, we’ve all got areas we’re trying to improve. This question opens up space for honest self-reflection, without judgment.
5. What do you think your younger self would be proud of you for today?
This connects past to present in such a wholesome way. Plus, it lets you peek into their journey, not just who they are, but how they got here.
6. Have you ever completely changed your mind about something important?
If yes, why? What happened? This shows growth, flexibility, and what experiences shifted their worldview.
7. What’s one mistake that taught you a valuable lesson?
It’s not about failure, it’s about bounce-back energy. This one’s a beautiful way to frame resilience. [Read: 36 Life Lessons to Instantly Transform Your Life & Draw In Happiness]
8. If your life was a book, what would this chapter be called?
Cheeky or serious, this makes people zoom out and reflect on their current arc. A little storytelling makes for a great connection builder.
9. What’s something you’ve forgiven yourself for?
Oof. Vulnerable, yes, but powerful. And if they’re still working on forgiving themselves? That’s okay too.
10. What’s a belief or habit that’s no longer serving you?
People love to talk about what they’re quitting, people-pleasing, doomscrolling, self-sabotage. It opens the floor to talk about transformation.
11. Do you trust your intuition? Why or why not?
How someone answers this tells you how much they rely on logic vs. gut feelings, and what’s guided their biggest life choices.
12. If you could master one personal skill instantly, what would it be?
It’s not just about goals. It’s about who they want to become, and what they wish they could already be doing better.
13. What kind of person do you never want to become?
Sometimes, knowing what you’re running from reveals just as much as what you’re running toward.
14. What’s something you’ve healed from that you never thought you could?
Use this one with people you already trust, it’s heavy, but beautiful. It invites honesty, and you might just learn something inspiring. [Read: What Is My Purpose in Life: 33 Secrets to Find Meaning When You Feel Lost]
Deep Questions About Family, Values & Beliefs
You can learn a lot about someone by how they talk about where they come from, not just their family, but the values, traditions, and beliefs that shaped them. These questions dive into the foundation of a person’s character.
They’re great for understanding long-term compatibility, finding common ground, or just seeing how someone processes life’s big stuff. Expect a mix of thoughtful, philosophical, and occasionally spicy answers.
1. What’s something your family did growing up that you want to continue, and something you never want to repeat?
Tradition says a lot about someone’s emotional wiring. This question helps you understand both what shaped them and what they’ve outgrown.
2. How did your family handle conflict when you were growing up?
Some families yell. Some go silent. Some pretend nothing happened and then explode three weeks later. This one tells you how someone learned (or didn’t learn) emotional regulation.
3. Do you believe people can truly change, or do we just reveal more of who we are over time?
A deceptively simple question, but their answer can reveal how forgiving, hopeful, or skeptical they are.
4. What do you think is more important in life, happiness or purpose?
This opens up a values hierarchy conversation, and their answer will tell you how they make big life decisions. [Read: 32 Secrets to Be Present & Live in the Moment When Life is Speeding Past You]
5. Is there a belief you were raised with that you’ve since questioned or outgrown?
We all inherit beliefs from our families or communities. This question explores how much someone thinks for themselves and what they’ve chosen to keep or let go.
6. What does the word “success” mean to you personally?
Whether it’s a six-figure paycheck, being present with family, or waking up without anxiety, this question tells you what drives them, and what they define as a “good life.”
7. What role does spirituality or religion play in your life (if any)?
It doesn’t matter what their beliefs are, what matters is whether they’re able to talk about it with openness and curiosity.
8. If you could change one thing about how you were raised, what would it be?
This can go deep quickly, but it gives you powerful insight into what someone needed as a kid but may not have gotten.
9. Do you think we choose our family, or are we just born into them?
This question leans a little philosophical. It’s great for sparking deeper debates around fate, loyalty, and chosen family. [Read: 30 Secrets to Start Over a New Life & Leave Your Past For a New Adventure]
10. What’s a value you live by, even when it’s inconvenient?
A question that filters out the fluff. People say they value things, but this one reveals what actually guides their choices under pressure.
11. What’s something you admire about the way someone else lives, even if it’s totally different from how you live?
This invites curiosity and open-mindedness. A person who can admire someone without needing to agree with them? That’s emotional maturity.
12. Do you believe people owe their parents anything once they become adults?
A spicy one. This question can spark passionate views on duty, boundaries, and generational expectations, so proceed with awareness.
Want to ask though provoking questions? Here’s what you need!
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Deep Questions To Ask Someone About Emotions & Vulnerability
These are the real ones, the questions that go beneath the “I’m fine” and “lol that’s crazy” layers. If you want to create a space where someone can feel safe being raw, these questions guide the way.
They’re best asked when there’s mutual trust, maybe during a quiet night drive, a long walk, or one of those late-night conversations where the walls come down and the masks come off.
1. What emotion do you struggle most to express, and why?
Anger? Sadness? Joy, even? This question goes beyond the basic “how are you” and asks them to reflect on how they process (or suppress) feelings.
2. When was the last time you cried in front of someone, and did it feel okay?
This isn’t about drama. It’s about emotional safety. The answer tells you whether they feel safe letting their guard down, and with whom.
3. Do you remember the first time you felt truly heartbroken?
Heartbreak shapes how we love and guard ourselves. Whether it’s a breakup, a betrayal, or something deeper, this reveals past wounds that still echo.
4. Is there a part of yourself you feel like you have to hide from most people?
This one opens up space for someone to show you what they usually protect. It’s a trust-builder, not a spotlight.
5. What’s something that makes you feel safe, instantly?
Everyone has a thing, a place, a person, a song. This question helps you understand what they need when life feels overwhelming.
6. When do you feel most alone, even if you’re surrounded by people?
It’s easy to feel isolated in a crowd. This gets to the root of what loneliness looks like for them, not just in general.
7. What’s something you’re afraid people would judge you for if they knew?
This one needs to be handled with care, but the answers can be surprisingly gentle, honest, and connective. [Read: 45 Positive & Negative Personality Traits that Can Change Your Life Forever!]
8. How do you want to be comforted when you’re having a really bad day?
Some people want space. Others want hugs and pizza. Knowing this is crucial if you’re building emotional intimacy.
9. Who’s someone that made you feel deeply understood, and what did they do?
This helps you understand their emotional blueprint, what “being seen” looks and feels like to them.
10. What’s something you’re still healing from, even if it happened a long time ago?
Not all wounds fade fast. This opens the floor for reflection, not to fix, just to witness.
11. When was the last time you felt truly peaceful?
Peace can be rare, so learning what brings them back to calm gives you insight into what centers them.
12. Have you ever put up emotional walls without realizing it?
A deeply reflective question that encourages them to think about their own defense mechanisms, and maybe recognize patterns. [Read: 41 Rules of Life to Never Be Unhappy & Be the One Who Screams “I Love My Life”]
Deep Questions to Ask Someone You’re Romantically Interested In
When there’s chemistry, tension, or “what are we?” vibes in the air, these questions help you shift from flirtation to emotional intimacy.
These aren’t your standard “what’s your type” questions, they’re designed to reveal how someone loves, what they want in a partner, and how emotionally available they really are.
Save these for when the connection is warm, there’s some level of mutual interest, and you’re ready to get real about compatibility.
1. What does love look like to you in everyday life?
Forget grand gestures, this reveals how someone gives and receives love through the little things. Words, actions, time? The answer might surprise you. [Read: 50 Questions for a New Relationship to Predict Your Romantic Future]
2. What scares you most about falling in love?
Behind the fear is usually a story, heartbreak, betrayal, or even fear of losing independence. This question opens up real emotional territory.
3. When do you feel most emotionally connected to someone?
Physical closeness? Deep talks? Shared silence? Their answer shows how they bond on a deeper level.
4. What’s one thing you need in a relationship that you didn’t always know you needed?
This is where past relationships meet present clarity. You’ll learn what they’ve learned, the hard way.
5. Do you believe in soulmates, or just good timing and hard work?
Romantic idealist or practical realist? This one reveals how they think about love, fate, and effort. [Read: 50 Best Relationship Topics & Things to Talk About in a Relationship]
6. What kind of emotional support do you wish more people understood you need?
This goes beyond “I’m here for you.” It tells you how to actually show up for them when it counts.
7. What’s your relationship green flag that you don’t think people notice enough?
Everyone talks about red flags, but this flips the script and highlights their strengths in love and loyalty.
8. Have you ever felt emotionally safe in a relationship? What made it feel that way?
This question gets real. If they’ve never felt that safety, it could open a powerful conversation.
9. What’s your love language, and what’s the one you struggle with most?
Knowing how they show love is great, but knowing what they don’t do naturally is even more telling.
10. If we were to date, what would you want our connection to feel like?
A little bold, a little flirty, and a great reality check to see if you’re on the same wavelength emotionally and romantically. [Read: 43 Things to Talk About With Your Crush & Make Them Think of You]
Ask the Right Questions, and You’ll Get to Know the Real Them
Some of these deep questions can feel scary to ask. Not because they’re too intense, but because deep down, we’re afraid we might not like the answer. What if they don’t believe what we believe? What if they’re not who we thought they were? What if the story we’ve built in our heads starts to unravel?
But real connection doesn’t come from fantasy, it comes from truth. If you’re falling for someone, or investing in a growing friendship, it’s better to know now than to be blindsided later. Emotional intimacy requires honesty, and sometimes, the most loving thing you can do is ask the question you’ve been avoiding.
That’s why these deep questions to ask a friend, or someone you’re getting to know, aren’t just conversation starters. They’re filters. They reveal values, vulnerabilities, emotional availability, and whether your connection is built on shared reality or imagined potential.
[Read: 35 Best Text Conversation Starters For The Shy & Socially Awkward]
So if you’re ready to connect, use these deep questions to ask a friend. Even if it’s hard. Especially if it’s hard. Because it’s better to be hurt by a truth today than disappointed by a lie you told yourself tomorrow.
