39 Deep Questions To Ask Your Crush or Friends

Deep Questions and Conversation Topics

My hand propped up my face as I sat at the table, a candle flickering between me and my date. If I looked at just the right angle, his head looked like it was going up in flames.

Soon, I realized I was staring at the fire and had completely zoned out, missing several minutes of what he was saying. Still, he talked, as if he hadn’t even noticed. I yawned daintily, if that’s even possible, attempting to hide it behind my hand. He still didn’t get the hint, rattling on about the pet tarantula he had when he was ten. When would this endless monologue be over?


I sat there, a blank look on my face. I fidgeted with anything I could find – the tablecloth, my napkin, the silverware. He seemed anxious too. “So how was your day?” he asked. “Good,” I answered. Silence. He’s so nice, I thought, but we have nothing in common. He was probably thinking the same thing as he slid his finger around the wine glass rim. I tried smiling to make him feel a little better. More silence. What do we talk about?

Have you ever been in a situation like these?

Interested in a meaningful relationship but unsure how to pursue depth? You’re not alone. A vast majority of Americans consider themselves lonely in some respect, and our world is growing increasingly drawn to dating sites and meet up apps to help people get together.

There is even a reality show out now called Married at First Sight, where people trust “love experts” to pick a mate that they will commit to marrying the first time they see them. We watch TV shows and movies about loving relationships, we read books about best friends having adventures – and we wonder where our true match is. Why are we so desperate for something that lasts? Why do we crave companionship? While we may not be able to answer what’s at the root of those desires, we can work on how to enhance relationships to achieve more connection and depth.

Questions are essential to a conversation. And we’re not talking about “What’s your favorite color?” type questions. If we never asked what someone else thinks, there would be a whole lot of boring one-sidedness, and relationships would fail pretty quickly. Have you ever known that person who never asks you anything about yourself? The show is all about him/her and you tend to lose interest in the first couple of minutes. Don’t be that person. Show your friends you care by interacting with them in a new way: deep questions!

Here we’ve generated a list of dozens of questions that you can use when seeking depth with some new or old friends/loved ones. Be bold with this list – the only way you can get more information about a person or get to know them better is by asking. We’ve split it up into categories based on the audience for the questions, but really you could ask each of the questions to anyone you know.

Remember – it’s probably not best to start out a brand new friendship with some of these questions. Small talk is still here for a reason, although it’s something I tend to avoid like the plague. Show your friend you respect them and treasure them by working your way up to the big questions, earning trust along the way.

Don’t push things too quickly. Start off basic with some questions about the space you’re in, weekend plans, and family. Make sure to comment as well, so that it doesn’t seem too much like an interview or a high-stakes interrogation. Take your time with relationships and reap the greater benefits after more time has passed. Once you’ve built a relationship with someone and mutual interest has been established, it’s time to move on and make progress by deepening the questions.

One quick, the overarching comment about questions – by adding “Why?” at the end of a question or as a follow-up, you can invite your friend/significant other to explore more meaning behind their response. Sometimes people blurt out the first answer that comes to mind, and while that can keep a conversation flowing, it may not deepen the relationship.

Deep Questions to Ask Friends

One of my favorite TV shows is Friends, where a bunch of guys and girls live in the same space and coexist in a quirky harmony with each other. There are plenty of ups and downs, but in the end, they’re always there for each other. How can we develop friendships like the ones we look up to? It all starts with (you guessed it) asking good questions. I’ve compiled a list here of questions for you to ask your good friend or even a friend you don’t know that well yet. Remember to listen to the answers, whether

  • If you could say something that everyone in the world would hear at the same time, what would you say?

This is honestly one of my favorite questions of all time. I ask it to people after I’ve known them for a while and can expect them to take their time when answering. If they get stuck on this one, let them absorb the question, maybe even move on and come back to it later.

  • What is an animal you feel like exhibits parts of your personality?
  • Do you feel in touch with your emotional center?

This question may seem a little New Age, but I think it’s nice to have open-ended questions that could be answered in a variety of ways. The other person can answer however they want, and the conversation can flow in several different directions.

  • What makes a person evil? Is it something genetic or learned from the environment?

Nature v. Nurture is a common psychological question, but it fits here because it could lead to a conversation about home lives, childhoods, and how much DNA impacts who we are.

  • What makes someone a true friend, not just an acquaintance?
  • What’s the strangest present you’ve ever received?
  • What’s something most people don’t know about you?
  • Do you enjoy deep conversations?
  • What’s something that makes you anxious?
  • Do you have any regrets?
  • If you could meet anyone, living or dead, and have lunch with them, who would you choose?
  • How would you like to be remembered? At your funeral, what do you want people to say about you?

Deep Questions to Ask Someone You Like

If you’ve never seen the movie She’s the Man, you’re doing something wrong with your life. If you have, you remember the scene where Amanda Bynes (disguised as her brother) is practicing conversation starters with Channing Tatum. They are scouring their brains for something to ask a question about, when suddenly Amanda Bynes says, “Ask her if she likes… Cheese!” Don’t be the guy/girl who asks their crush whether they like a dairy product.

You’ve found that special someone and you’re ready to make a move. Or maybe you’ve already started a relationship with that person and are ready to take it to the next level… Now’s your time to shine with some great conversation starting questions!

This gets kind of tricky, though, right? How do we let another person know we’re interested in finding out more about them without giving too much away? There’s a certain pleasure in the pursuit of another person, and that is only enhanced by deep questions. The better you know each other, the stronger the bond and the higher the likelihood of a lasting relationship. Studies show that the best romantic relationships are based on deep friendships – help make yours last with a few of these questions.

  • When’s the last time you felt truly loved or appreciated?
  • What are some things that have improved in the last 50 years? Some things that have worsened?
  • What causes loneliness? Why don’t we create more meaningful relationships when that’s all anyone craves?
  • If you could play an instrument that reflects your personality, what would you play?
  • Who’s your biggest fan, your biggest supporter?
  • Describe a color you love without using any color words.
  • How have your family’s roles changed since you were a child?
  • Tell a story about a time when you felt like faith was real.
  • Have you ever been out of the country? What did you learn? How were things different? How were things the same?
  • Do you feel more one with yourself in the city or out in nature?
  • What makes humanity successful?
  • If you could blink your eyes and be anywhere, where would you go?
  • What’s the most beautiful thing happening in the world right now? The ugliest?

Deep Questions to Ask a Girl

These are deeper questions for your best friends at a sleepover – don’t just go tossing these around unless you’re ready for a real conversation. They can apply to guys too (but for more guy-specific questions, keep scrolling).

  • Do you think we learn our behaviors or are born with them?
  • What’s something that helps you get out of bed every morning?
  • Who’s a TV character who you can relate to?
  • What’s the most beautiful songs you’ve ever heard?
  • What do you think makes the world worth living in?
  • Why did you choose your current job?
  • What’s something you’re afraid to jump into?
  • What’s something that infuriates you?

Deep Questions to Ask a Guy

Again, these questions can be used for guys or girls, so don’t feel restricted by the question categories. Be open with your guy friends and encourage them to channel their softer side when answering. Learn more about them with some of these fun and deep questions.

  • What’s a time you’ve felt on top of the world? An adrenaline rush?

This question opens up an opportunity to talk about survival stories or risky situations the other person has been in (guys tend to love that stuff), or it could be a chance to discuss a time they just felt really great about themselves doing something important, which is also a good self-esteem boost.

  • What’s an event in your life that impacted who you are?
  • What’s one goal you have for the next ten years?
  • How do you feel about gender roles? Is there any truth to them?
  • Were people created to build or destroy?
  • How is the world similar to the world your grandparents grew up in? How is it different?

Take some of these questions to your next coffee date and try them out. Sit around the campfire with some close friends and hear each other’s deepest feelings and fears. Set up a tea time and pass around a jar of tough questions so that each person has to answer one. Be confident in your answering – it will create an environment of openness for the others in the room.

The more forthcoming and open you are about yourself, the safer others will feel to be vulnerable with their responses. Don’t be afraid to be bold with your questions – the worst they can do is say they’d rather not respond.

Let’s go back to those scenarios we talked about at the beginning. Imagine tackling those conversations with some solid deep questions – no more rambling, no more awkward silence. The date would be infinitely smoother since there would be a balance between both people talking back and forth. In the dictionary, conversation means the informal exchange of thoughts (http://www.dictionary.com/browse/conversation). This exchange becomes more meaningful when we ask questions that we genuinely want to hear the answer to. If you’re simply asking questions to fill space, the other person may feel unappreciated or unimportant. Ask to better understand. Ask to comprehend. Ask to love someone else more effectively.

Now that you have some top-notch questions, I have one more piece of advice for you – LISTEN. Too many people hear what the other person has to say while only thinking about what they will say in response. Instead of planning your response, try absorbing what the other person has to say. And when they’re finished, give the words space to breathe by simply sitting in silence. It may feel uncomfortable at first, but sometimes even that helps strengthen the bond.

Enjoy your conversations!