How Old Am I Meant to Be?

Thought-provoking questions to deepen your connection

It's late, the lights are low, you're a little tired but not ready to go to bed yet—the perfect time for a deep late-night conversation. Worried about how to get the ball rolling? Don't be! We've got over 100 questions here that are sure to stoke meaningful discussions that help you get to know each other better and build strong emotional bonds.

Top Late Night Conversation Starters

What's the most recent thing you've learned?
What legacy would you like to leave behind?
What experience had the biggest impact on who you are today?
If you could live in any fictional world, where would you live?
If you had only 1 year to live, what would you do differently?

Steps

Simple Questions to Get to Know Someone Better

{endbold}If you haven't known someone for very long but think you'd like to build a closer relationship, a quiet late-night conversation is a great way to make that happen. At the same time, you don't want to ask something that gets too personal too quickly. Start with a softball question that helps the two of you get more comfortable with one another, such as one of these:
- How would you define courage? What's the bravest thing you've ever seen?
- What songs would be on the soundtrack of your life?
- What are you the most grateful for?
- If you could have dinner with anyone, living or dead, who would you choose? What would you eat, and what would you talk about?
- What have you accomplished that you're most proud of?
- What would be your weapon of choice in the zombie apocalypse?
- If you were a superhero, what would be your superpower?
- What's a common adult issue that no one prepared you for or warned you about?
- Add your favorite deep conversation starters to wikihow's "What are some good deep convo starters to ask?" forum. Don't forget to check out what other readers are suggesting, too!

Juicy Conversation Starters

{endbold} If you happen to be getting into a deep late-night chat with your romantic partner, it might not take long for the late hour and the quiet, intimate atmosphere to get the two of you in the mood for a more sensual discussion. Late-night heart-to-hearts are the perfect time to discuss your sexual fantasies, interests, and preferences and get to know each other on a deeper level. Here are some great questions to get you started:
- What ways do you like to be touched?
- What's your favorite part of my body?
- Do you like to be in charge during sex, or do you prefer if your partner takes control?
- What's something that always gets you in the mood?
- What's your biggest sexual fantasy that you haven't tried to fulfill yet, but want to?
- Do you have any kinks or fetishes, or are there any that you're curious about?
- How would you describe your sexuality?
- What's the most adventurous thing you've ever done in bed?
- Asking your partner about their physical preferences can help you show your love in a way they’ll enjoy.

Funny Conversation Starters

{endbold} Deep doesn't have to mean serious! You can also have a really deep, meaningful conversation with someone while both of you are laughing your butts off. Laughter triggers the release of feel-good chemicals that make you feel happy to be around each other, which means you'll feel safer being vulnerable and opening up. Here are some questions that might potentially get the giggles flowing:
- If you could understand what animals are saying, which one do you think would be the rudest? Can you give an impression of what it would sound like?
- What's the best joke you've ever heard?
- Can you make me laugh solely by making weird facial expressions?
- What's the most ridiculous thing you've ever looked up online?
- Would you rather fight a human-sized duck or the number of regular-sized ducks equal to the weight of an average human? How big is an average human?
- Which meme best represents your life as a whole?
- What fashion trend did you follow in the past that's cringe to look back on now?
- What's a word that you pronounced incorrectly for years before anyone told you?

About Preferences, Favorites, and Interests

{endbold}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. These types of questions also help you unlock more commonalities or learn about something you're not familiar with. 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?
- Do you prefer going out and being active or staying in and relaxing?
- What's your favorite way to be active or get exercise?
- Where is your favorite place to be active?
- 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, Work, and Money

{endbold}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?
- Do you believe that the early bird catches the worm or that slow and steady wins the race?
- 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?
- If you could go back and start over right now in an entirely different field, what would you choose and why?
- 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?
- How much money do you think you'll need to save to retire? What age do you want to retire?

About Dreams and Fantasies

{endbold}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 would 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?
- You are granted the power to live for one day as any other animal. What animal do you choose, and what do you do?

About Family and Childhood

{endbold}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.^[1] 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 and family:
- 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?
- Which family member did you relate to the most as a kid? Did that person change as you got older?
- 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?
- Who do you consider to be "family"? What does that word mean to you?

About Love and Romance

{endbold}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?
- What are your favorite ways to show someone 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 Beliefs and Values

{endbold}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. Get to know each other better with questions like these:
- 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?
- 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?
- What do you consider your ethnic or cultural group? How do you identify with that group (or identify yourself as a member of it)?
- 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?
- Have your beliefs stayed the same throughout most of your life or have they changed a lot?
- 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?
- If we were really just living in a simulation, what law of physics would you want to "break"?

About the Past

{endbold}When you reminisce and feel nostalgic, you also feel closer and more deeply committed to the person you're reminiscing with.^[2] 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?
- What decade do you think would have been the most exciting decade to be alive?

About the Future

{endbold}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?
- If you were immortal, how would that change how you live your life?

For Close Friends

{endbold}Your BFF may be someone you could talk the sun up with—but there still might be things you don't know about each other. Asking probing questions can help you learn more about your friends and even find more things about them that you love. Here are some questions for those late-night gabfests with a good friend:
- What was your impression of me when we first met?
- What was your favorite adventure that the two of us had together?
- What does friendship mean to you?
- What's a book that you think I should read?
- What were you surprised to learn about me?
- What's the most difficult thing you've ever done?
- Is there anything you would change about our friendship?
- What's more important in a relationship, loyalty or honesty?

For Romantic Couples

{endbold}When you're hanging out late at night with your romantic partner, it's only natural to want to talk about love and how you feel about each other. The best deep conversations come from questions that make you think about your relationship in a different light. Here are some romantic questions to try:
- When did you first feel attracted to me?
- What would happen on your perfect date?
- What are 3 things we have in common?
- How would you describe me to someone who'd never met me before?
- What's your favorite way to spend time with me as a couple?
- What area of our relationship do you think is the weakest?
- What's something you think is too serious to be joked about?
- Why do you think I'm attracted to you?

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.^[3]
- 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. 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.
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.^[4]
- 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.^[5]
- Eliminate any distractions and make eye contact throughout the conversation—it helps build the emotional intimacy between the two of you.^[6]
- Give the other person your undivided attention to show them that you value them and believe they are worth spending time on.
- 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.^[7]
- 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!^[8]
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.^[9]
- 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).^[10]
- 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.^[11]
- 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.