About Preferences and Favorites
Learning about each other's favorite things—as well as the things you detest—is a great way to find common ground and discover new things about each other. The secret is to ask questions that scratch below the surface and require a little introspection to answer. Get started with these questions that focus on the best things in life: What is the healthiest thing you do to take care of yourself? What is your favorite guilty pleasure? What food or dish most reminds you of home? What's your favorite thing to do when you have 15 minutes to burn? How would you describe your perfect day? If you had 2 extra hours in a day, how would you spend them? What do you think about the most when you let your mind wander and aren't actively thinking about anything?
About Hobbies and Interests
Like preferences, learning what someone is passionate about and what they want to spend their time doing can tell you a lot about what kind of person they are and what makes them tick. These kinds of questions help you unlock more commonalities or learn about something you're not familiar with. Here are some to get you started: What's your favorite way to be active or get exercise? What's the most recent thing you've learned? What would most people think is your most unexpected interest? Is there anything that you're secretly good at? If not, tell me about something you wish you were secretly good at. When was the last time you sang to someone? What's something you're really good at making or building? Is there something you used to really enjoy that you stopped doing? What made you stop? What's keeping you from doing it again?
About Goals and Aspirations
You can learn a lot about what someone values by finding out what they want to do with their life and how they see themselves living in the future. If you're considering spending the rest of your life with the person you're talking to, these types of questions can also help you figure out if the two of you have compatible visions. Use these conversation starters to find out what someone hopes to achieve: What's the most recent thing you've learned? What was the first thing you remember aspiring to do? Tell me about a goal that you had to abandon. Do you want to try again? What's something you've always wanted to know how to do? What's kept you from learning it? Would you sacrifice money for freedom? Would you sacrifice freedom for money? Where do you really see yourself in 10 years? How does that differ from the answer you might give to that same question in a job interview? If you had to choose between either fame or fortune, knowing that either way you would live comfortably for the rest of your life, which would you choose?
About the Future
You can learn a lot about each other by talking about your visions for the future—what you hope will happen, as well as what you fear might happen. Finding out what someone thinks about the future gives you some insight into their general outlook and perspective on life. Here are some questions to get you started: What legacy would you like to leave behind? What's something you hope to do in the next year that you've never done before? If you could live anywhere in the world, where would that be? What random thing now do you think you'll be nostalgic about in 20 years? How do you think social media will evolve in the future? What do you think people 100 years from now will say about this year? Which would you rather have, flying cars or high-speed rail?
About Dreams and Fantasies
Dreams and fantasies give you a really fun, low-pressure way to get vulnerable with each other and talk about some potentially tough topics in a lighter way. After all, it's just a fantasy, right? Try these fun questions to talk well into the night: If a genie granted you 3 wishes right now, what would you wish for? If you were guaranteed to become famous for something, what would you most want to be famous for? If someone designed an amusement park based on your life, which ride would have the longest line? You encounter a powerful magical being who offers to transform you into any animal for 24 hours. Which animal do you choose and what would you do? You can send a message that will be simultaneously transmitted to and understood by every person on the planet. What does your message say? If you can time travel but you can only go in one direction, do you choose to travel to the past or to the future? If you could live in any fictional or fantasy world, where would that be?
About the Past
When you reminisce and feel nostalgic, you also feel closer and more deeply committed to the person you're reminiscing with. That makes talking about the past a great way to start a deep late-night conversation. Here are some conversation starters to get things going: What year or era do you have the most nostalgia for? What was it like in your hometown when you were a kid? What events of your past had the biggest impact on who you are today? What do you consider your greatest accomplishment in life so far? What do you consider your biggest mistake (or biggest regret) in life so far? If you could go back in time and give your younger self one piece of advice, what would it be? If you could travel back to a time before the internet, what would you do?
About Childhood and Upbringing
How someone was raised can tell you a lot about what kind of person they are, including how they show love and how they react to conflict. Talking about your childhood often requires you to be vulnerable as well, which helps deepen your connection to the person you're talking to. Try these conversation starters related to childhood: What's a toy you had growing up that you wish you still had? Who was your best friend when you were a kid? What was your favorite thing about childhood? What do you remember being your first favorite food? What's your favorite childhood memory? What's your most cringe childhood memory? How did your family celebrate holidays when you were growing up?
About Family and Relationships
Questions about the different kinds of relationships we have with each other can stimulate some of the deepest and most meaningful conversations. Often, it's through these relationships that you figure out who you really are. Here are some questions you can start out with: What is your relationship with your family like? What's your favorite family tradition? Who in your family can you be the most honest with? What would you change about the way your parents raised you? Would you rather have a large, sprawling family or a small, close-knit family? What gives you a sense of family or makes you feel like you belong? What's your favorite nickname or term of endearment for yourself, and who calls (or called) you that?
About Money and Charity
When you get into questions about money and charity, you're touching on someone's core values—what's really important to them and the way they live their life. Better understanding someone's attitude toward money gives you some real insight into what they truly value and want to keep in their life. Here are some conversation starters you can try: If you could do anything you wanted and money was no object, what would you do? If someone gave you money to start a business, what kind of business would you start? What was the first thing you ever bought with your own money? If you get a windfall of money, is your instinct to spend it, save it, or invest it? Tell me about a recent random act of kindness you performed for a stranger. If you had $1 million to donate to the cause of your choice, which nonprofit organization would you choose? Would you rather be poor and in love or rich and alone?
About Work and Career
A lot of people don't necessarily like talking about work. But when you dig below the surface and start talking about what you want to do with your life, you're really talking about your core values—all of those things that make you who you are. Here are some questions to get you going: When you were a little kid, what did you want to be when you grew up? If you were guaranteed a livable income, what career would you most want? What do you find fulfilling about the work that you do? Do you consider what you do a calling? What drew you to the field you're currently in? Is it like you expected it would be? When you're approaching a group task, do you tend to lead, follow, or get out of the way? If you could do any one thing to improve your workday, what would it be?
About Love and Romance
Whether you have a romantic connection with the person you're talking to or not, love and romance can make for the perfect late-night conversation topic. The lights are low, things are quiet, you're feeling cozy. Here are some warm, fuzzy conversation starters you can use: Tell me about the first time you ever fell in love, or thought you were in love. How do you like to receive affection? Have you ever experienced love at first sight? What is the biggest red flag for you in a new relationship? What's the worst date you've ever been on? Who are your relationship role models? How would you know that you wanted to spend the rest of your life with someone?
About Personal Beliefs
When you're asking about personal beliefs, you're really getting down to who someone really is. Answering these questions honestly requires some vulnerability, but you'll understand each other much better and feel more connected as a result. Learn more about each other with these questions: What's some of the best advice you've ever gotten? Do you follow it? Which fictional character do you relate to the most? Tell me about something that happened to you that caused you to change your mind about something important. What are 3 things you are grateful for right now? What do you believe is the most important issue facing the world right now? How would you resolve it? What does your personal utopia look like? How about your personal dystopia? Is it more important to you to follow the rules or to do what is morally or ethically right?
About Social and Cultural Issues
Talking about society and culture can go from relatively light topics to real hot-button issues with the potential to start some heated debates. But as long as you keep an open mind, you can come out of the conversation with a new understanding of different points of view. Consider these conversation starters: What cultural traditions do you think should be preserved? Which should be eliminated? If you had the power to completely resolve a single social or political issue forever, what issue would you choose? Tell me about your most memorable experience with "culture shock." If you could instantly be fluent in any one language that you don't already know, which would you choose? What does gender mean to you? What's a name that's been ruined for you because of someone terrible who has it? How do you find new art and music?
About Religion and Spirituality
Religion might be one of those topics you've been warned to stay away from if you want to keep the peace. But if you approach the conversation with curiosity rather than judgment, you'll likely find that you feel closer to each other as a result. Try these questions for a more spiritual conversation: Do you believe in God or some higher power? How do you know what's right and wrong? What do you believe happens when we die? How much of a role does chance or randomness play in what happens? What is the most awe-inspiring thing you've ever seen or experienced? How does your zodiac sign accurately represent you? Would you convert to a different religion for your life partner?
About Life and Existence
What topic could possibly be deeper than the meaning of life, the universe, and everything? If all else fails, talking about the philosophy of life and existence will definitely keep you up into the wee hours of the morning. Start your minds spinning with these questions: What's one thing you think people frequently misunderstand or get wrong about you? You have the power to eliminate a major world problem forever, but for every problem you eliminate, the person you love the most must die. What problems do you eliminate? If you found out you had only 1 year to live, what would you change about your life? What's stopping you from making those changes now? Do you believe humans can ever truly live in harmony with nature? When logic tells you one thing and your gut tells you another, which one do you go with? What do you believe is the purpose of your life? What question do you hope is included here because you're afraid to ask me?
How to Have a Meaningful Conversation
Set the stage for emotional intimacy and connection. Ideally, choose a quiet, comfortable spot where you can hang out with minimal distractions or interruptions. Soft, low light is great. You might also put on some soft music in the background—just make sure it's quiet enough that neither of you feels like you have to talk over it. It's also best if you're sitting close to the person you're talking to—you can reach out and touch their hand or arm as you listen. Plus, you'll likely feel mentally closer if you're physically close to each other.
Approach the conversation with a sense of curiosity. Getting a deep conversation started can be intimidating, especially if you're just starting to get to know somebody. Ask a question because you're deeply interested in the answer. Instead of judging, aim to better understand where the person is coming from. It can help to add a little fun to it and make it like a game. For example, you could take turns asking each other questions from this article.
Give the conversation your undivided attention. The simple act of paying full attention to someone when they're speaking—making eye contact and eliminating any distractions—builds the emotional intimacy between the two of you. Put your phone on silent and turn off anything in the background that might distract the two of you from each other. When you give someone your undivided attention, you signal to them that you find them valuable and worth spending time on. It's much easier to feel safe opening up when you know that the other person wants to hear what you have to say.
Ask open-ended questions that allow for elaboration. A question that can be answered with a single word isn't going to be the easiest way to get a conversation going. Better questions call for the person to tell a story in the answer to discuss a big issue on a deeper level. When you ask open-ended questions, you also send a subtle signal to the other person that you're really interested in whatever's on their mind—you want to go below the surface. You can even turn a yes/no question into an open-ended question by tagging "and why" to the end of it—although these aren't always the most interesting questions, they can still get someone talking!
Listen actively and seek clarification when you need to. Research shows people feel more emotionally connected to each other when they're both present and mindful during conversations. When you listen actively, you prioritize what the other person is saying over what you might want to say next. You also make sure you understand what they meant before you respond. If you don't understand something the other person said, asking for clarification lets them know that you think it's important to understand exactly what they're saying. The easiest way to make sure you've understood someone correctly is to repeat back to them what they've said using their own words. Doing this also gives you a little time to come up with your response (assuming you understood them correctly).
Share stories about yourself openly and honestly. People are often afraid of what will happen if they share something sensitive about themselves, but research shows that people tend to be pretty receptive. If you share something meaningful, most people will try to share something meaningful in return and keep the conversation going. Don't be afraid to admit if you find the answer embarrassing or if you need some time to formulate your answer before you respond to a question. At the same time, if you feel uncomfortable answering anything, let the person know! Emotional intimacy can be tough and you might find yourself hitting some walls that you weren't aware you had—and that's okay!
Empathize and validate the other person's feelings. Remember that even if you disagree with what someone says, their emotions are still valid. When you want to empathize with someone, focus on how they feel rather than how they react as a result of those feelings. Acknowledge the person's feelings and give them space to process the emotions that came up, if they need it. You might even thank them for feeling safe enough to tell you. For example, if your friend is talking about something they did in childhood that they regret, you might say, "You must have been terrified! It's totally understandable that you would act the way you did—I'm sure a lot of people would do the same thing. You were very brave to face that."
Use follow-up questions to better understand. The key to keeping a conversation going is to listen to what the other person is saying and find something within what they've said to ask about. If you can't pinpoint anything specific that seems natural to expand upon, try asking either how it made them feel or what happened next (whichever makes more sense given what they've said). For example, if a friend is talking about their childhood and mentions that they watched cartoons with their dad on Saturday mornings, you might ask them what their dad's favorite cartoon was. If they're recounting a memory, you might ask them how they felt in the moment or how they feel thinking back on it now.
Why are deep conversations important?
Deep conversations build and strengthen emotional connections. Deep conversations require people to be vulnerable with each other. You'll trust someone and feel closer to them each time you're safely vulnerable around them. When you open up and speak to someone about what's on your mind in a meaningful way, your bond grows stronger. A lot of people use small talk as social lubricant, but studies show people actually prefer deep conversations to small talk—even with complete strangers. Humans are social creatures that crave connection.
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