160+ Interesting Questions to Ask Your Friends, Family, Crush, or Strangers

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Plus, communication pros explain how to listen and build a connection

Co-authored by Kirin Dejonckheere and Aimee Payne, MFA

Last Updated: April 13, 2025 Fact Checked

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• Deep
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• Personal
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• Random
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• Funny
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• For Girls
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• For Guys
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• For Friends
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• For Family
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• Coworkers
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• For Strangers
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• FAQs

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Are you looking for interesting questions to ask the people in your life to start a great conversation or get to know them better? If so, we’ve got your back. This article gives you plenty of truly interesting questions to make your friends, family, coworkers, and even strangers think. Plus, we spoke with experts in interpersonal communication to get their best advice for asking good questions and having better conversations.

Top Interesting Questions to Ask People

• What brings out your inner child?
• How have you changed in the past year?
• What’s your favorite form of potato?
• What’s the worst haircut you've ever had?
• Who are your relationship role models?
• When was the last time you cried?
• Do you consider what you do a calling?

Steps

Section 1 of 12:

Deep Interesting Questions to Ask

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1. 
   Ask someone a deep question to learn more about who they are. According to certified life coach Kirin Dejonckheere, having good conversations is “not always about talking a lot or bringing up these crazy topics…It’s more about asking the right questions.” Try the list of deep questions below to spark interesting conversations:

   • Who’s your greatest role model?
   • What brings out your inner child?
   • What are you most grateful for in life?
   • What is something that gives you hope?
   • Where do you go to get inspired?
   • What do you think makes someone a good person?
   • How would you spend your last day on earth?
   • What’s one thing you’d change about yourself if you could?
   • What’s the best gift you’ve ever received?
   • What makes you feel most alive?
   • What is the last completely spontaneous thing you did?
   • What is the most surprising thing people don’t know about you?
   • What keeps you up at night?
   • What brings you the most happiness in life?
   • Which of your personality traits are you proudest of?
   • Do you enjoy being in a place where people don’t know you?
   • How do you want people to describe you?
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Section 2 of 12:

Personal Interesting Questions to Ask

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1. 
   Move past small talk to really understand someone. According to dating coach Lauren Sanders, “When you meet a new person, ask them about their life goals and values, their upbringing, their most recent committed relationship, their current career plans to further it, and their first impression of you.” This helps you move past pleasantries and learn what someone’s about. Here are a few personal questions to help you get started:

   • What scares you the most?
   • If you could erase one memory, what would it be?
   • Do you think you’re too critical of yourself?
   • Are you more spiritual or religious?
   • Who would you call in an emergency, and why?
   • How have you changed in the past year?
   • What do you miss most about being a child?
   • What’s the quickest way someone can lose your trust?
   • Do you think physical or emotional pain is worse?
   • Do you care what people think of you?
   • What is one thing you can’t live without?
   • Are you very close to your family?
   • How does your personality change when you’re around a different group of people?
   • When do you feel most vulnerable?
   • What was your impression of me when we first met?
   • What’s the last lie you told, and why did you tell it?

Section 3 of 12:

Random Interesting Questions to Ask

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1. 
   Start an interesting conversation with an off-the-wall question. Sometimes, the best conversations come from the most random—and weirdest—questions. A random question is also a great way to lighten the mood when things get a little too deep. Try one of these to break any tension and keep the conversations going:

   • If you have an accent, do your thoughts have an accent, too?
   • Does time flow forward, or is time an illusion?
   • How well is your home fortified against a zombie apocalypse?
   • Is it a little sus that doctors call their business a practice?
   • If you had to listen to one song over and over for a whole day, what would it be?
   • What’s the weirdest thing you own?
   • What would be your job if you worked at a circus?
   • Would you rather have horns or grow a tail?
   • What’s the first thing you would do if you woke up tomorrow as your 15-year-old self?
   • If you had to have a third ear, where would you want it to be?
   • How would someone know if a word is misspelled in the dictionary?
   • Would you rather have a whole crowd of mediocre friends or one loyal dog?
   • What do you talk about when you talk to yourself?
   • Would you rather be kidnapped by pirates or aliens?
   • What’s your favorite form of potato?
   • Did anything exist before the universe? If so, what?
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Section 4 of 12:

Funny Interesting Questions to Ask

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1. 
   Make someone think and laugh at the same time with a funny question. Laughter is a great way to improve your mood and strengthen your relationships. It can also help enhance teamwork and relieve tension. Ask one of these funny questions to start an interesting conversation with a smile:

   • Why do round pizzas come in square boxes?
   • Is a hot dog a sandwich?
   • What’s the dumbest thing you’ve ever looked up online?
   • Would rather be 3 feet shorter or 3 feet taller?
   • What’s the worst fashion trend you still kind of like?
   • What’s the worst song ever written?
   • What’s the worst haircut you've ever had?
   • What’s your most useless skill?
   • What’s the most embarrassing song on your playlist?
   • What celebrity would you challenge to a duel?
   • What’s one thing everyone looks ridiculous doing?
   • Would you rather talk like Yoda or breathe like Darth Vader?
   • What’s a word you pronounced wrong for years before figuring it out?
   • Which meme best represents your life?
   • Would a mermaid give birth or lay eggs?
   • What’s your favorite smell?

Section 5 of 12:

Interesting Questions to Ask Girls

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1. 
   Learn more about her with a few thought-provoking questions. Dejonckheere recommends finding similar interests to make a connection with a girl, “because once you find an interest that you both connect on, then you can go deeper.” Here’s a list of interesting questions to help you find common interests that will spark a deeper conversation:

   • What makes you smile on a bad day?
   • Do you think you’ve already met your soulmate?
   • Do you have a specific type of person you’re drawn to?
   • Do you usually fall in love quickly, or do you take your time?
   • Do you think exes can stay friends?
   • How do you like to receive affection?
   • Who are your relationship role models?
   • Do you enjoy compliments or struggle to accept them?
   • Have you ever been truly hurt in a previous relationship?
   • How would you know you wanted to spend the rest of your life with someone?
   • What are your favorite ways to show affection?
   • Do you think cheating is ever justifiable?
   • What’s the weirdest thing you find attractive about people?
   • Do you believe in monogamy?
   • What are your relationship dealbreakers?
   • Have you ever been in love before?
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Section 6 of 12:

Interesting Questions to Ask Guys

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1. 
   Ask him an intriguing question to dig into his personality. When you’re talking to a guy you’re in a relationship with, or even one you’re just interested in, it’s perfectly acceptable to ask them a few interesting questions. Sanders advises, “Ask them about the first time they fell in love. You could also ask them why things didn’t work out with their first love….Ask them about their last breakup, and why it didn’t work out.” Here are a few more options to help you really understand him:

   • What’s your favorite way to unwind?
   • Do you believe there’s one soulmate, or do people have multiple soulmates?
   • What’s the biggest lesson you learned from your last relationship?
   • Do you see yourself ever getting married?
   • What conventionally attractive traits do you find unattractive?
   • What would your perfect date look like?
   • What’s the biggest red flag for a new relationship?
   • Do you think it’s okay to tell white lies in a relationship?
   • What about you do you think is the hardest thing to love?
   • What’s the worst date you’ve ever been on?
   • What’s your biggest pet peeve in a partner?
   • Do you think physical or emotional compatibility is more important?
   • What type of person was your first love?
   • What kind of person do you picture yourself ending up with?
   • What 3 words would your exes use to describe you?
   • Do you believe in love at first sight?

Section 7 of 12:

Interesting Questions to Ask Friends

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1. 
   Build a deeper bond with your friends by asking them questions. Take your friendship beyond a superficial level by having more meaningful conversations. Plus, asking questions about their life is a great way to show a friend you care. Try to uncover what your friends want out of life with the questions below:

   • What’s the best piece of advice you’ve ever received?
   • Is there anything I do that makes you feel especially supported?
   • When did you feel most betrayed by a friend?
   • What is your favorite thing about our friendship?
   • If you could have coffee with one person, dead or alive, who would it be?
   • What does friendship mean to you?
   • What’s more important in a friendship, loyalty or honesty?
   • What character or person would you choose to be in a love-hate relationship with?
   • When was the last time you cried?
   • Have you ever had an imaginary friend?
   • What was something you were surprised to learn about me?
   • What’s your favorite adventure the 2 of us have had together?
   • Is there any part of our friendship you’d change if you could?
   • How do you usually deal with conflict in friendships?
   • Do you tend to make friends with people who are like you or who are very different?
   • What do you think it means to be a good friend?
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Section 8 of 12:

Interesting Questions to Ask Family

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1. 
   Catch up with your family members with thoughtful questions. Certified leadership and life coach Christina Stathopoulos recommends that you make the conversation more meaningful and personal by asking “the kind of question that only that person could answer.” Then, really focus on listening to them and understanding what they’re saying. Here are a few great questions that can lead to interesting conversations with family members:

   • What’s your favorite childhood memory?
   • What’s the weirdest family story you can remember?
   • What was the most memorable vacation you went on as a child?
   • Who in your family did you feel closest to when you were growing up?
   • If you could describe our family in one word, what would it be?
   • What’s the biggest lesson your parents taught you?
   • Who in our family do you feel you can be most honest with?
   • What in your life has had the biggest impact on who you are today?
   • If you could go back in time before the internet was invented, would you?
   • What year of your life do you have the most nostalgia for?
   • What’s a toy you had when you were a kid that you wish you still had?
   • Which of your parents’ traits do you admire the most?
   • How did your parents decide what to name you?
   • Did you enjoy growing up in your hometown?
   • What’s your favorite family tradition?
   • Who is our most eccentric family member?

Section 9 of 12:

Interesting Questions to Ask Coworkers

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1. 
   Ask an interesting question to find out what makes your coworker tick. “If you try to deepen the connection, try to bring the conversations outside of work,” advises Dejonckheere. Getting them to talk by asking them interesting questions helps to create a moment of connection. Just make sure to back off if they don’t seem comfortable talking about their personal lives at work. Try one of these questions to move toward a better relationship with a coworker:

   • If you could have any fictional character for a coworker, who would it be?
   • Would you sacrifice money for freedom? Or vice versa?
   • Do you believe the early bird catches the worm or that slow and steady wins the race?
   • What would your younger self think of the job you have now?
   • Do you consider what you do a calling?
   • If you could rewind your career and start from scratch, what would you do differently?
   • If you won the lottery tomorrow, what would be the first thing you’d buy?
   • What do you believe your life’s purpose is?
   • If your brain tells you one thing and your gut tells you another, which do you trust?
   • Have your beliefs mostly stayed the same throughout your life, or have they changed?
   • If someone gave you money to start a business, what business would you start?
   • If you could do one thing to improve your workday, what would it be?
   • If you were guaranteed a livable income, what job or career would you pick?
   • When you were a kid, what did you want to be when you grew up?
   • Where do you really see yourself in 10 years?
   • What’s the most recent thing you’ve learned at work?
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Section 10 of 12:

Interesting Questions to Ask Strangers

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1. 
   Break the ice with someone new by posing an interesting question. Licensed clinical psychologist Donna Novak strongly recommends asking questions to break the ice with someone new because people tend to really get engaged with questions. Thought-provoking questions like the ones below can really make a difference when you’re getting to know someone:

   • What’s one thing you do on a daily basis that no one knows you hate?
   • What’s one topic you know so much about that you could write a book on?
   • What kind of person were you in high school?
   • What’s your most controversial hot take?
   • Is it important to forgive people who have wronged you?
   • Do you find it easy or hard to let go of the past?
   • What’s something in your life you’re choosing to ignore right now?
   • Would you rather lose all of your memories or never be able to make new ones?
   • What do you think being famous is like?
   • Would you rather be able to look into the future or change the past?
   • What’s one thing you’d do if you knew you couldn’t fail?
   • Do you believe there’s anything worth killing or dying for?
   • If you could put up a statue of someone, who would it be, and why?
   • Are you more like your mom or your dad? How so?
   • What’s the best decision you ever made?
   • What role do you play in your friend group?

Section 11 of 12:

Having Interesting Conversations

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1. 1
   Use active listening skills. “It's always very important to show curiosity and listen actively because a lot of people just want to be heard,” Dejonckheere says. Using active listening skills means keeping your attention focused on the other person. Then, show you’re listening by maintaining eye contact and leaning slightly toward them as they speak.

   • “If you're truly present and curious in a conversation with anyone, then the next question that you ask will undoubtedly be meaningful,” suggests Stathopoulos.
   • Above all, avoid interrupting the other person when they’re speaking. Not only is it rude, but it also shows you weren’t really paying attention to them.
2. 2
   Ask open-ended questions to go deeper or get clarification. Open-ended questions encourage the other person to give more than a 1-2 word answer. They commonly start with “What,” “Why,” “How,” or “Tell me about…”

   • Open-ended questions are also great when you’re asking follow-up questions because they let the other person know you’re interested in hearing more.
   • Examples of open-ended questions are: “How did that make you feel?”, “What was that like?”, or “Why did you choose that?”
3. 3
   Avoid being judgmental about what they’re telling you. Whether you’re meeting someone new or getting to know them better, keep an open mind and make an effort to see things from their point of view. After all, everyone has different experiences, and this is your opportunity to learn why they believe something or act in a way that you don’t agree with.

   • Make a conscious effort to cut the other person some slack if they share something you’re inclined to be judgmental about.
   • If they tell you about something they’ve done that you disapprove of, try to separate the action from the person.
   • Remind yourself what it’s like when someone is judgmental toward you without knowing your side of the story.
4. 4
   Be willing to be vulnerable. Being more vulnerable in a relationship means you’re willing to share your fears, regrets, and insecurities with the other person. If you’re willing to share your deeper emotions with someone, they’re much more likely to feel close to you. It also helps you feel closer to them.

   • When you’re vulnerable with someone, you allow them to see your authentic self, which can lead to a more genuine relationship.
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Section 12 of 12:

FAQs about Asking Interesting Questions

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1. 1
   How do you manage social anxiety when getting to know someone? If you suffer from social anxiety, meeting a new person can trigger symptoms like a shaky voice, butterflies in your stomach, or a racing heartbeat. There are a few different things you can try to help lower your stress levels when talking with someone new:

   • Challenge negative thoughts like, “They’re not going to like me,” or “I’m going to embarrass myself.”
   • Instead, say something to yourself like, “How do I know they won’t like me? They don’t even know me yet,” or “Even if I make a social misstep, are they really going to laugh at me?”
2. 2
   What should you avoid when asking questions? Try to stick with asking one question at a time. Sometimes, when you’re eager to learn more about someone, you might throw multiple questions at them, which can get overwhelming. Instead, take your time and listen to their answers. Then, really engage with their response by restating it in your own words or asking a follow-up question.

   • Ask questions that not everyone would ask. They don’t have to be completely out of left field. A surprising question is automatically more interesting than a common question.
   • When you ask a question, pause for a moment. Give them time to think about how they want to answer. A short pause after a question is normal and not something to worry about.
   • Avoid asking yes-or-no questions that don’t encourage someone to open up.
3. 3
   Why is it hard to ask someone questions to get to know them better? Some people don’t ask questions because they’re worried about people judging them. Others may be afraid of offending the other person or seem like they’re overstepping boundaries.

   • The best way to handle this fear is to ask the question and be sensitive to the person’s answer.
   • Pay attention to how the person reacts to your question. If they look thoughtful or engaged, you probably haven’t offended them.
   • If they seem upset or refuse to answer, it gives you the opportunity to apologize and withdraw your question.
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