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Communication coach Christina Morara gives expert advice on how to ask good get-to-know-you questions
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Asking fun questions is a great way to deepen your relationship with someone, whether they’re a new friend, coworker, or date. But what if you’re not quite sure what questions to ask to get to know someone better? That’s where we come in! We’ve compiled the ultimate list of get-to-know-you questions for just about any situation. We even interviewed communication and dating experts for their insights on the best icebreaker questions to ask and how to have an engaging conversation. Keep reading for everything you need to know!

Best Questions to Get to Know Someone

Communication coach Cristina Morara says a trick for crafting good icebreaker questions is to “ask the question that you would like to be asked of you.” Here are a few examples of fun get-to-know-you questions to ask new friends, coworkers, or dates:

  • What’s your go-to karaoke song?
  • What’s your biggest pet peeve?
  • What’s your favorite season of the year?
  • Where in the world do you feel happiest?
  • Would you want to be famous? Why or why not?
  • What’s your Roman Empire (something you think about a lot)?
  • Which fictional world from a movie or book would you want to live in?
Section 1 of 9:

Fun Get-to-Know-You Questions for Anyone

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  1. When it comes to getting to know new people, “I really would urge people to ask a question, because people tend to get really engaged with questions,” says licensed clinical psychologist Donna Novak, Psy.D.[1] So, if you’re going somewhere where you’ll be interacting with a lot of new people (like a social gathering, networking event, or new school), consider having a few of these fun get-to-know-you questions in your back pocket:
    • What’s your go-to karaoke song?
    • What’s your biggest pet peeve?
    • If you could only eat one food for the rest of your life, what would it be?
    • Do you have a comfort TV show or comfort movie?
    • What’s the coolest thing you’ve read or watched this week?
    • What’s your most-used emoji over text?
    • What’s your go-to midnight snack?
    • If you could take a vacation anywhere in the world, where would you go?
    • Would you rather time-travel to the future or the past?
    • What’s the most spontaneous thing you’ve ever done?
    • What superpower would you want to have?
    • If you could have an unlimited supply of something, what would you choose?
    • If you could spend the day with a fictional character, who would it be?
    • What’s the best gift you’ve ever gotten?
    • What’s your favorite thing to do on the weekend?
    • What’s been the highlight of your week so far?
    • Do you like trying new things or sticking to a routine?
    • What’s a new hobby you’d love to try?
    • Do you have a favorite place to visit in this town/city?
    • What’s something you think is seriously underrated?
    • What’s one thing you really love about yourself?
    • What’s the last thing that made you laugh out loud?

    Meet the wikiHow Experts

    Cristina Morara is a communication coach, dating coach, and professional matchmaker. She is the founder of Stellar Hitch Private Matchmaking, a luxury matchmaking service in Los Angeles.

    Donna Novak, Psy.D, is a licensed clinical psychologist with over 10 years of experience. She specializes in treating anxiety and relationship concerns.

    Lauren Sanders is a professional matchmaker, dating coach, and the founder of Dating for the Soul. She specializes in helping singles find love.

    Kirin Dejonckheere is a certified life coach who provides both online and in-person coaching sessions tailored to her clients’ needs, personality, and desired outcomes.

    Amiccio is a social events organization based in NYC that hosts social events to help people make new connections in the city.

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Section 2 of 9:

Fun Get-to-Know-You Questions for New Friends

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  1. Connect with a new friend with one of these fun get-to-know-you questions. If you want to deepen your relationship with a new friend, asking each other interesting questions is a great place to start. In fact, studies show that “reciprocal self-disclosure” (which means revealing personal information about yourself and having another do the same) dramatically increases feelings of closeness.[2] Here are some of our favorite questions to ask:
    • What book do you wish you could read for the first time again?
    • Do you have a favorite podcast?
    • What TV show could you binge-watch for a whole day?
    • If you won the lottery, what’s the first thing you’d buy?
    • What’s your go-to takeout order after a long day?
    • Do you have a favorite dish to cook?
    • Have you picked up any cool new hobbies lately?
    • If you could only eat one meal the rest of your life, what would it be?
    • Do you believe in astrology? Why or why not?
    • If you could wake up tomorrow with a new skill or talent, what would you choose?
    • Where in the world do you feel happiest?
    • Do you have any favorite family traditions?
    • Did you have a favorite childhood TV show or movie?
    • What’s one place you’ve always dreamed of going?
    • What was your most embarrassing moment?
    • What’s your favorite season of the year?
    • Do you collect anything cool?
    • What’s the best concert you’ve ever been to?
    • If you had to describe yourself in one word, what word would it be?
    • What does the perfect Saturday look like to you?
    • What’s one thing that you think is totally overrated?
    • What’s the last movie you saw in theaters?
    • Did you have a silly childhood nickname?
    • Would you want to be famous? Why or why not?
    • What’s something that inspires you creatively?
    • If you were a mythical or supernatural creature, which one would you be?
    • Do you think your vibe is more sunrise, sunset, twilight, or night?[3]
Section 3 of 9:

Fun Get-to-Know-You Questions for Dates

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  1. Good get-to-know-you questions for dates range from lighthearted to deeper, more vulnerable options. “Ask them about their family history, where they come from, and what they’re searching for in a relationship,” says matchmaker and dating coach Lauren Sanders. Just be sure not to overdo it! Sanders recommends narrowing it down to the most important 4-5 questions to keep the date from feeling too much like an interview.[4]
    • What were you like in high school?
    • Does your family have any special holiday traditions?
    • Where did you grow up?
    • Did you enjoy growing up in your hometown?
    • What’s your favorite local spot to hang out at?
    • Do you like spicy food?
    • Do you prefer small talk or deep convos?
    • What’s the craziest dating experience you’ve ever had?
    • Do you have any dating pet peeves?
    • What’s at the top of your bucket list?
    • Do you have any cool hobbies?
    • What’s the last TV show you loved?
    • What kind of music have you been into lately?
    • Do you have any pets?
    • How do you like your coffee in the morning?
    • Are you more of an outdoorsy or indoorsy person?
    • What’s the most daring food item you’ve ever tried?
    • What’s the best piece of dating advice you’ve ever gotten?
    • Which actor would you want to play you in a movie about your life?
    • What’s one movie you can watch over and over again?
    • Are you more of a texter or a caller?
    • What’s your love language?
    • Who was your first celebrity crush?
    • What fictional character do you have a crush on?
    • What’s the worst pick-up line you’ve ever heard (or used)?
    • Do you have any dealbreakers in romance?[5]
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Section 4 of 9:

Fun Get-to-Know-You Questions for Coworkers

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  1. Ask one of these fun icebreakers to get to know a coworker better. You spend a ton of time with your coworkers each week, so why not take some time to connect with them as a person? Certified life coach Kirin Dejonckheere recommends asking questions about topics outside of work, while making sure you stick to work-appropriate topics. She says questions about their family, the sports they like, and how they spend their time outside of work are all great options![6]
    • What’s your favorite sport to watch?
    • What’s your favorite sport to play?
    • Do you prefer silence or listening to music while working?
    • If you could only listen to one album for the rest of your life, what would it be?
    • What’s your favorite weekend activity to do with your family?
    • What’s the funniest thing you’ve ever experienced?
    • What was your first job? Did you enjoy it?
    • What was your dream job when you were little?
    • Did you grow up around here, or somewhere far away?
    • Do you have any restaurant or coffee shop recs to share?
    • Do you prefer group projects or solo projects?
    • Do you prefer working from home or working in the office?
    • If you could teleport anywhere in the world right now, where would you go?
    • If you had no responsibilities for a full year, how would you spend it?
    • What’s your favorite vacation memory?
    • Do you enjoy traveling solo, or do you prefer going in a group?
    • Which of your past jobs was your favorite and least favorite?
    • What career advice would you give your younger self?
    • Which celebrity would you be most starstruck by if you met them?
    • What’s your favorite type of gift to receive on your birthday?
    • What’s the best part of your day?
    • What’s one big goal you have for the next year?
    • What’s one thing you’re looking forward to right now?
Section 5 of 9:

Fun Get-to-Know-You Questions for Students

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  1. Whether you’re a student looking for icebreakers to use with your classmates or a teacher looking for a way to encourage your students to connect, you’re bound to find some questions you love in this list!
    • What’s your favorite animal?
    • What’s the best birthday present you’ve ever gotten?
    • What’s your favorite song to sing?
    • If you could be friends with a cartoon character, who would you pick?
    • What’s the best family vacation you’ve ever been on?
    • Do you have a pet?
    • Do you have any siblings?
    • Do you have a favorite memory with your family?
    • What’s your favorite holiday?
    • What’s your favorite food?
    • What job do you want to have when you grow up?
    • Who is your favorite Disney character?
    • Have you ever been to a concert?
    • Do you play any sports?
    • Have you ever gone camping?
    • Do you have any funny nicknames?
    • If you could visit any place in the world, where would you go?
    • Would you rather be able to fly or read minds?
    • Do you speak any other languages?
    • What’s your favorite ice cream flavor?
    • Do you have a favorite superhero?
    • What’s the bravest thing you’ve ever done?
    • What’s something about yourself that makes you proud?
    • If you were the president for a day, what would you do?
    • If you could meet a celebrity, who would you pick?
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Section 6 of 9:

Silly Get-to-Know-You Questions

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  1. Keep things lighthearted with these silly get-to-know-you questions. If you want to get to know someone better while maintaining a fun, easygoing energy, these humorous questions are the ones for you. Plus, there’s no better way to connect with someone than to share a laugh! Here are some options to try out:
    • What’s the cringiest thing you’ve ever done?
    • What’s one famous mystery that you’re dying to learn the answer to?
    • Would you rather be able to fly or read minds?
    • What’s the weirdest food combo you’ve ever tried?
    • What’s one completely useless talent you have?
    • What’s your Roman Empire (something you think about all the time)?
    • What’s your beige flag?
    • What’s your guilty pleasure song or TV show?
    • Which app on your phone do you use the most?
    • If you were a fruit, which one would you be?
    • What’s your favorite breakfast cereal?
    • What wild animal would you want as a pet?
    • Would you ever go to outer space?
    • Do you believe in aliens?
    • Do you believe in ghosts?
    • In your opinion, what’s the worst song in the world?
    • If you could get rid of one music genre, what would it be?
    • Do you sing in the shower?
    • Who is your most embarrassing “hear me out” character?
    • Which fictional world from a movie or book would you want to live in?
    • What’s the most ridiculous online purchase you’ve ever made?
    • If you had to teach a class on a niche topic, what would it be?
    • If you could swap lives with a fictional character, who would you choose?
    • If you could invite one famous person to dinner, who would you choose?
    • If you could pick one chore to never have to do again, which one would you pick?
Section 7 of 9:

Fun This-or-That Questions

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  1. You can tell a lot about a person by their tastes and preferences, even about things that seem silly or inconsequential. For example, are they an early bird or a night owl? Do they prefer minimalist or maximalist decor? These types of questions reveal tons about someone’s personality!
    • Sweet or savory?
    • Early bird or night owl?
    • Cats or dogs?
    • Swimming pool or beach?
    • Summer or winter?
    • Halloween or Christmas?
    • Hot tea or iced tea?
    • Driver or passenger?
    • Comedy or horror?
    • Cocktail or mocktail?
    • Night in or night out?
    • Vacation or staycation?
    • Pizza or pasta?
    • Waffles or pancakes?
    • Hamburgers or hot dogs?
    • Silver or gold?
    • Minimalist or maximalist?
    • Podcasts or playlists?
    • Physical books or eBooks?
    • DC or Marvel?
    • TikTok or Instagram?
    • Sunrise or sunset?
    • Casual or formal?
    • Playing sports or watching sports?
    • Flowers or chocolates?
    • Home-cooked meal or takeout?
    • Movies or TV shows?
    • A lifetime of free clothes or a lifetime of free food?[7]
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Section 8 of 9:

Deep Get-to-Know-You Questions

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  1. Take things to the next level with these vulnerable questions. If you’re on a third or fourth date or hanging out with a friend you’ve already known for a while, these deep questions are a great way to grow your connection. “Of course, there are the usual conversation topics of where you’re from or what you do,” says Kevin Wang of Amiccio, a social events organization based in NYC. The next level would be passions, hobbies, places you’ve been, interests you want to pursue, or skills you want to improve on, Wang explains.[8] Here are some examples:
    • What’s something that people would be surprised to learn about you?
    • What’s the best piece of advice you’ve ever gotten?
    • What’s something you’ve always wanted to do, but haven’t tried yet?
    • Which of your achievements are you most proud of and why?
    • Would you want to live forever? Why or why not?
    • What’s one piece of art that completely changed your life?
    • Have you ever been in love before?
    • What’s your biggest fear in life?
    • If you could go back in time and change one decision, which one would you pick?
    • What do you do to make yourself feel better when you’re having a tough day?
    • Who’s the first person you call when you need advice about something?
    • What is something you truly love about yourself?
    • What’s something you would change about yourself if you could?
    • What traits impress you the most in other people?
    • What do you think is most important, stability or excitement?
    • When do you feel most confident?
    • What’s your favorite childhood memory?
    • Do you have a close relationship with your parents?
    • Do you prefer giving or receiving gifts?
    • Who’s the person in your life that you admire the most?
    • Do you believe in the supernatural?
    • If you only had one day left on Earth, how would you spend it?
    • What does friendship mean to you?
    • Do you trust people easily?
    • If you could give your past self one piece of advice, what would it be?
    • Are you happy in your current career path?
    • What does success mean to you?
    • What was the biggest setback you’ve ever faced, and how did you overcome it?
    • What do you think is your main purpose in life?
Section 9 of 9:

How to Have Good Get-to-Know-You Conversations

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  1. When getting to know someone new, Morara says, “A trick is to think ahead of time of what you want them to know about you, and then ask that very question.”[9] This accomplishes two things: Number one, if you’d find it fun to be asked that question, chances are they’d enjoy being asked the question, too. Second, it gives you a chance to share interesting facts about yourself, since they’ll likely ask you the same question when they’re done answering.
    • For example, if you’re a big traveler. Morara recommends asking questions like, “Where have you traveled?” or “What’s one of the coolest places you’ve been to date?”[10]
    • Then, in turn, the other person will likely ask you the same question, and you’ll be able to share your experiences, too. You get to see whether you have this shared interest, and you also get to talk about a topic that really matters to you!
  2. 2
    Practice active listening while they’re answering your questions. “It’s always important to show curiosity and listen actively because a lot of people just want to be heard,” explains Dejonckheere.[11] Active listening shows that you care about what the other person is saying, and it involves things like using engaged body language, reacting to what they’re saying with your facial expressions, and maintaining eye contact.[12]
  3. 3
    Ask interesting follow-up questions to deepen the conversation. Once the other person has answered your question, don’t just say “Oh, cool!” and let the conversation end there. Instead, ask a thoughtful follow-up question to really dig in and explore the topic more. This is another foundation of active listening, and it does wonders for truly getting to know someone through conversation![13]
    • For example, if you ask someone what their favorite vacation destination is, and they say “Italy,” ask them more questions to learn more about why they like it so much.
    • Questions like, “What do you love so much about visiting Italy?” “Do you have any favorite dishes you tried there?” or “What was your favorite sightseeing excursion in Italy?” are all great options.
  4. “The important thing is for the conversation not to be lopsided,” says Wang. “One side can’t be feeling like they are talking too much or too little, or asking all the questions or being asked all the questions.”[14] If you notice that the other person has been asking you most of the questions and letting you talk most of the time, make an effort to slow down and ask them more questions, so they get a chance to share about themselves, too!
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References

  1. Donna Novak, Psy.D. Licensed Clinical Psychologist. Expert Interview
  2. https://ggia.berkeley.edu/practice/36_questions_for_increasing_closeness
  3. https://www.mtu.edu/student-leadership/student-orgs/rso-resources/virtual-resources/fun-icebreaking-questions.pdf
  4. Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
  5. https://www.wondermind.com/article/first-date-questions/
  6. Kirin Dejonckheere. Certified Life Coach. Expert Interview
  7. https://parade.com/1208432/marynliles/this-or-that-questions/
  8. Amiccio. Social Events Host. Expert Interview
  9. Cristina Morara. Communication Coach. Expert Interview
  1. Cristina Morara. Dating Coach. Expert Interview
  2. Kirin Dejonckheere. Certified Life Coach. Expert Interview
  3. https://www.simplypsychology.org/active-listening-definition-skills-benefits.html
  4. https://hr.mit.edu/learning-topics/comm/articles/active-listening
  5. Amiccio. Social Events Host. Expert Interview

About This Article

Cristina Morara
Co-authored by:
Dating Coach
This article was co-authored by Cristina Morara and by wikiHow staff writer, Annabelle Reyes. Cristina Morara is a Professional Matchmaker, Dating Coach, Relationship Expert, and the Founder of Stellar Hitch Private Matchmaking, a luxury matchmaking service based in Los Angeles that serves clients nationwide and internationally. As a former casting director, Cristina specializes in finding the perfect partner through her exclusive global network and detailed, warm approach. Cristina holds a BA in Communications and Psychology from Villanova University. Stellar Hitch has been featured in the Huffington Post, Chelsea Handler’s Netflix documentary, ABC News, the Tonight Show, Voyage LA, and the Celebrity Perspective.
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Updated: December 10, 2025
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Categories: Questions
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