260+ Icebreakers to Ask Someone to Get to Know Them

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Flirty and fun questions to help you get to know them more deeply

Co-authored by Lauren Sanders and Dev Murphy, MA

Last Updated: April 28, 2025 Fact Checked

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• Personal
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• Deep
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• Flirty
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• Unique
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• Funny
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• For Dating
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• Career
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• Best Tips for Asking Questions

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Whether you’re prepping for a first date or just hoping to become besties with a new acquaintance, having some icebreakers in your back pocket can help you get to know them more deeply. That’s why we’ve compiled a list of personal, romantic, and fun questions to ask someone to break the ice! We also talked to professional matchmaker and dating coach Lauren Sanders about the best questions to ask someone on a date to find out if there’s long-term potential. Plus, we’ve got tips for how to ask questions effectively so you can really get to know someone.

Best Questions to Ask Someone to Get to Know Them

• What do you value most in friendships?
• How do you define love?
• What’s your idea of a “perfect” day?
• What’s the weirdest thing you’ve taken a pic of with your phone?

Steps

Section 1 of 8:

Personal Questions to Ask to Get to Know Someone

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1. 
   Dive deep with these authentic get-to-know-you Qs. Chit-chat has its place: it can help you warm up to someone and ease into a “real” conversation. But these questions will help you get down to the nitty gritty and let you really get to know each other:

   • What do you value most in friendships?
   • If you could have any talent, what would you choose?
   • What is the biggest compliment you can give someone?
   • Do you think you’re a friendly person?
   • What do you wish you did more of?
   • What is something that makes you really angry?
   • Have you ever told a lie that you regretted?
   • What are you most proud of?
   • Are you an organ donor, and how did you come to that decision?
   • What is your definition of success?
   • What’s your least favorite emotion?
   • If you had the opportunity to redesign society, what would you change?
   • What do you love most about life?
   • How do you express your love for someone?
   • Do you believe you should do one thing a day that scares you?
   • If you could change your relationship with a family member, would you? If so, with whom?
   • How do you show your family you love them?
   • What is something you consider too serious to joke about?
   • Have you ever had an epiphany?
   • If you could do any other job, what would it be?
   • What does spirituality mean to you?
   • Do you believe what is meant for you will never miss you?
   • What impresses you the most?
   • Who in your family makes you feel the safest?
   • What life lessons have you had to learn the hard way?
   • What’s your least favorite part about being you?
   • What’s the best piece of advice a family member has given you?
   • Did you ever hide anything from or lie to your parents?
   • What’s your favorite family tradition?
   • Do you ever wish you were raised differently?
   • How do you show kindness to others?
   • How do you define beauty?
   • What line should someone never cross with you?
   • What do you think makes someone a “good person”?
   • How do you react to anger from others?
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Section 2 of 8:

Deep Questions to Ask to Get to Know Someone

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1. 
   Get a little more up-close-and-personal with these thoughtful questions. A surefire way to learn more about another person is to ask them about their values, their upbringing, and other more things that define who they are. Asking deeper questions will allow you to get a better idea of who the person you’re speaking to is under the surface, and how they move through the world.

   • What do you think it means to be healthy?
   • What’s one dream you wish you could accomplish?
   • Do you wish you had more siblings? If so, why?
   • What’s one lesson life has taught you?
   • Do you consider yourself a people pleaser?
   • What’s the toughest conversation you’ve ever had to have?
   • What is one thing you think most people have and never appreciate enough?
   • What’s the best gift you’ve ever received?
   • Where is the fanciest place you’ve ever been?
   • What, if anything, do you think happens after death?
   • What's your favorite way to spend time with your family?
   • What does true friendship mean to you?
   • Who are you closest to in your family and why?
   • What are things people can do that make you feel valued or appreciated?
   • What was your happiest memory of us together?
   • How can someone earn your trust?
   • What’s your idea of a “perfect” day?
   • What’s your greatest fear?
   • Do you live by any piece of advice or motto?
   • When was the last time you cried in front of someone?
   • Do you believe in astrology? Why or why not?
   • Are you active on social media, or do you prefer to be more private?
   • What do you miss most about being a kid?
   • Where do you get your news?
   • Would you rather be the worst player on a good team or the best player on a bad one?
   • If you could live to age 90 and keep either your 30-year-old mind or your 30-year-old body, which would you choose?
   • What’s the first thing you look for in a partner and/or friend?
   • When someone walks past you, what grabs your attention first?
   • Do you believe in second chances?
   • What mannerisms have you realized you got from your parents?
   • If you had a crystal ball, what would you want to know?
   • What are some of your most fun moments in the past year?
   • Is there any topic you feel should be off-limits for jokes?
   • Which would you rather spend, time or money?
   • What’s your greatest accomplishment in life?
   • What activity makes you feel alive?
   • What are some experiences you’ve had that really affected the person you’ve become?
   • What was your last random act of kindness?
   • If you could, what moment in your life would you replay?
   • What small thing makes you happy?
   • When was the last time you cracked up laughing? Why?

Section 3 of 8:

Flirty Questions to Get to Know Someone

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1. 
   These saucy and sassy icebreakers will make your date blush. Want to get to know your date a little better? These flirty questions will help you find out more about what they’re looking for in a relationship and whether you’re compatible—while also letting you have plenty of fun and igniting some serious chemistry:

   • Do you believe in fate, or do you think we create our own destiny?
   • Who is your “hear me out”? What do you think it says about you?
   • If we could spend the whole night together, what would you want to do?
   • If your life was a rom-com, what songs would be on the soundtrack?
   • What is the cheesiest pickup line anyone’s ever tried on you? Did it work?
   • Can I see the last selfie you took? Tell me the story behind it.
   • When was the last time someone made you blush?
   • How direct would you want someone to be if they had feelings for you?
   • Do you scream on roller coasters? What if you were holding my hand?
   • What’s the top song on your make-out playlist?
   • Would you rather spend a whole day with me or a whole night with me?
   • Who was your celebrity crush when you were growing up?
   • What’s your idea of a perfect date?
   • Which family member has had the greatest impact on you?
   • What’s the best compliment you’ve ever received?
   • If you could kiss any fictional character, who would it be?
   • What’s your favorite couple's Halloween costume?
   • What’s your idea of a perfect weekend getaway?
   • Have you ever been kicked out of a public place, and if so, what’s the story?
   • What’s your go-to dance move, and can I see it?
   • What do romance movies get wrong most of the time?
   • Which is better: makeup sex or breakup sex?
   • Would you be more likely to say yes to bar trivia night or a sunrise hike for a date?
   • If you could have any superpower, what would it be?
   • What’s the most disturbing thing under your bed?
   • If you had to watch the same movie every day for a month, what would it be?
   • What’s the most adventurous thing you’ve ever done?
   • If you designed your ideal dating app, what would it look like?
   • What’s the worst date you’ve ever been on?
   • If you were in a biker gang, what would your nickname be?
   • What’s a hidden talent you have that most people don’t know about?
   • Are you a morning person or a night owl? And do you prefer morning dates or evening dates?
   • Has anyone ever told you that you are the most stunning person in the world?
   • What’s your favorite cuisine, and what dish should we try together?
   • What was the best thing that happened to you today?
   • What’s a song that you’ll never admit to liking but secretly love?
   • If you could have a romantic dinner with anyone from history, who would it be?
   • What’s the silliest argument you’ve ever gotten into with a stranger?
   • What’s one movie you feel super passionate about?
   • What’s your favorite guilty pleasure?
   • What’s your favorite way to spend a rainy day?
   • What’s one fact you wish every guy/girl understood?
   • What always makes you laugh?
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Section 4 of 8:

Unconventional Questions to Get to Know Someone

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1. 
   Weird icebreakers make for the most memorable conversations! Want to make sure your next hangout is one they’ll never forget? Try asking some of these atypical get-to-know-you questions to learn something truly unique about them!

   • When you were a child, what was your favorite dinosaur?
   • If you could animorphs-style transform into one animal for 30 minute increments, what would that animal be?
   • If you could set up a teleporter in your house that could go to one location, where would that location be?
   • If your aura had a color, what color would it be?
   • If your likeness was to be turned into a statue, in what pose would you like to be immortalized?
   • What is the strangest thing you have ever eaten?
   • If you ended up with the dream job of your 5-year-old self, what would you be doing right now?
   • Who’s your favorite painter or what’s your favorite piece of visual art?
   • If you were a cartoon character who wore the same outfit every day (as they do), what would that outfit be?
   • At what point did your life seem most like a sitcom scenario?
   • Do your best impression of the goofiest laugh you could possibly think of.
   • Do an impression of what your favorite animal would sound like if they could speak our language.
   • Action heroes always say “Danger is my middle name.” What would be your middle name if it was an attribute that describes you?
   • Describe the most awkward photograph you have ever taken.
   • You have a budget of a million dollars to pull an epic prank. What’s your plan?
   • If your life had a soundtrack, which music artist or composer would you want to create it?
   • What scent would you turn into a candle if you could use any scent?
   • If you had to become a supervillain, which hero would be your arch-nemesis?
   • If you were a ghost, who and where would you haunt?
   • What is a song you love that might surprise people?
   • What holiday tradition do you wish you could do every single day?
   • What is the best witty comeback you thought of hours or days later?
   • What is something you tried to blame on a sibling? Did you get away with it?
   • What is an interaction you had with a stranger that you still think about from time to time?

Section 5 of 8:

Fun Questions to Get to Know Someone

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1. 
   Getting to know someone doesn’t just mean posing deep questions. It’s also about having fun together and learning more about what the other person enjoys, what makes them laugh, and how they like to spend their time. Besides, studies show laughing with someone helps you both loosen up and bond more easily! Ask these fun and friendly questions to make them giggle:

   • What’s a movie or TV show you could watch every day?
   • Do you have a favorite memory?
   • Which of your personality traits are you most proud of?
   • What makes you feel at peace?
   • Would you rather make more money doing a job you hate or less doing one you love?
   • Do you have any pets?
   • If you could have dinner with anyone in the world, who would you choose?
   • What’s the most memorable compliment you’ve ever received?
   • What’s the weirdest thing you’ve taken a pic of with your phone?
   • What’s on your travel bucket list and why?
   • You’re doing karaoke. What song are you singing?
   • What’s your favorite sport to watch?
   • What’s something you read today that made you smile?
   • Would you rather spend the day at a botanical garden or in an art museum?
   • What types of books do you like to read?
   • What do you daydream about?
   • What is your favorite food?
   • What is your claim to fame?
   • What is a skill you’ve always wanted to learn?
   • Do you have a favorite TV show?
   • Do you have a morning routine?
   • What’s the most relaxing part of your day?
   • Are you good at solving puzzles?
   • What job would you never want to do?
   • What are you most excited about for the future?
   • What do you think the ultimate theme party would be?
   • Do you believe in ghosts?
   • If you had the opportunity to know the future, would you want to know?
   • Where is the most beautiful place you have ever seen in person?
   • Would you rather know how you will die or when?
   • What’s your favorite thing to do for exercise?
   • Which app on your phone do you use the most?
   • Do you prefer cooking dinner or going out?
   • Do you sing in the shower?
   • Are you double jointed in any way?
   • What’s the first thing you do in the morning?
   • What, in your opinion, is the worst song ever recorded?
   • What’s your favorite kind of weather?
   • Coffee or tea?
   • Do you like cities or remote places better?
   • Would you survive a zombie apocalypse?
   • What’s your dream career?
   • Which unconventional animal do you wish you could keep as a pet?
   • What is one super-specific museum you would visit?
   • If you could get rid of any genre of music, which would it be?
   • Would you rather have the ability to fly or the ability to teleport?
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Section 6 of 8:

Questions to Ask to Get to Know Someone You’re Dating

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1. 
   Find out how compatible you and your date really are. Sanders says there are a few important questions you should ask on a date to see if you make a good match—including questions about your goals, expectations, and potential dealbreakers. If you want to see if your relationship has some longevity, break out some of these get-to-know-you questions:

   • What are your long-term goals?
   • How do you define love?
   • Do you like small talk?
   • What’s your biggest insecurity?
   • How has your opinion of your family changed over the years?
   • Have you ever experienced true love, and how did you know?
   • If you’re close with your family, what’s the hardest part about spending time away from them?
   • What’s your love language?
     • “Everybody has a different love language,” says Sanders. She notes that asking a new partner their love language early on, and then showing them love in that language, is a great way to help them feel valued and develop chemistry.
   • What’s more important in life: excitement or stability?
   • What are your needs in a relationship?
   • Do you wish you had a bigger family, or are you happy with its current size?
   • Do you often listen to your intuition?
   • What is something you have never truly wrapped your head around?
   • What’s one thing you learned from your last serious relationship?
   • Are you proud of yourself?
   • Do you hold grudges or do you let go of things easily?
   • What do you consider your core values?
   • How would you describe a perfect date night?
   • Do you think you have a true calling?
   • What’s something that makes you envious?
   • Do you tend to trust people easily?
   • What brings you the most joy?
   • Can you tell me about the first time you fell in love? Why didn’t things work out?
   • Can you tell me about your worst online dating experience? What happened?
   • What caused your last relationship to end?
   • How do you feel about children? Would you like to have children someday?
   • How do you feel about marriage? How do you envision a long-term, committed relationship?
   • Are you religious, or do you have any spiritual affiliation?
   • Where do you see yourself in the next five years, financially?
   • What’s something that makes you feel overwhelmed?
   • What can you tell me about your family?
   • How do you like to receive support in times of need?
   • What’s one thing that scares you about relationships? What’s something you love about them?
   • What are you looking for in a relationship?
   • What are some ways you’ve been working to develop yourself lately?
   • What’s your relationship deal breaker?
   EXPERT TIP

   

   Lauren Sanders

   Matchmaker & Dating Coach

   Lauren Sanders is a Professional Matchmaker, Dating Coach, and the Founder of Dating for the Soul. With over four years of experience, she specializes in helping singles find love. Lauren is also the author of Lipstick Faith: A Collection of Inspirational Writings and Life Lessons, You Deserve the World, Rainbows and Strawberries: 100 Devotions for the Brighter Side of Life, and Let's Go Outside Mommy. Lauren holds BS from Dillard University and a Masters from The University of North Georgia.

   

   Lauren Sanders
   Matchmaker & Dating Coach

   Discussing life goals early in the relationship will help you establish common ground. My clients that do actually end up being in a relationship, or even getting married one day, have common goals for the future. That helps to increase their chemistry, because they can see a future together.

Section 7 of 8:

Career-Related Questions to Get to Know Someone

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1. 
   Ask them about their professional dreams to get a sense of their life goals. Whether the person you’re trying to get to know better is a colleague, a friend, or a romantic interest, these questions can help you get an idea of where they see their career heading and how they envision the future. They’ll also tell you something about their values, passions, and work ethic.

   • How did you end up in your current job?
   • If you could have another career, what would it be?
   • What's your absolute dream job, and has it changed since you were 11?
   • If you could switch roles with anyone at your company, who would it be?
   • What’s the biggest misconception about your job?
   • If you could only choose one word to describe your working style, what would it be?
   • What’s the best thing you’ve ever achieved in the workplace?
   • What’s one thing that’s been challenging for you recently?
   • What are your professional goals for the next year?
   • What’s the best career advice you’ve ever received?
   • What would you choose an unlimited supply of in the office?
   • What’s the most memorable moment in your career so far?
   • What’s your favorite thing about working in your industry?
   • What’s your go-to productivity playlist or music?
   • What’s something you’re passionate about outside of work?
   • If you could change one thing about your job, what would it be?
   • What’s the best work-related book you’ve read?
   • How do you like to unwind after a busy or stressful day?
   • What’s your favorite way to celebrate a work-related achievement?
   • If you could automate one part of your job, what would it be?
   • If you could work remotely from anywhere in the world, where would you choose?
   • Who is your dream career mentor?
   • What’s the most rewarding part of your job?
   • What is your most productive time of day?
   • If you could design your perfect office, what would it look like?
   • What’s your favorite quote or mantra that motivates you at work?
   • What’s the most fun project you’ve ever worked on?
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Section 8 of 8:

How to Ask Questions to Get to Know Someone Better

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1. 1
   Actively listen when they respond. Active listening is about showing the other person you’re paying attention and that you’re invested in what they’re saying. Some ways to show you’re listening include maintaining eye contact, nodding occasionally, and asking good follow-up questions.

   • Active listening lets the other person know you’re interested in learning more about them, who they are, and their experiences. It’s a great way to build trust and help them want to open up to you.
   • Another great tip? Make sure you’re giving the other person your undivided attention while they’re speaking, instead of trying to think about what you’re going to say next!
2. 2
   Approach the conversation with curiosity. Even if you’ve got great questions prepared, the interaction is likely to fall flat unless you maintain curiosity and propel the conversation forward. Rather than hop from question to question, dive deeper into the questions that interest you or that the person you’re talking to seems particularly interested in.

   • Not only can being curious about their answers help you both dive into deeper, more personal waters, it’ll likely help them feel valued and like what they’re telling you matters—which is also a great way to bond!
   • For instance, if they answer the question “What’s one thing you value in your friendships?” with “I value laughter,” you might reply with, “Which of your friends do you laugh the most with?” or “What makes you laugh?”
3. 3
   Stay open-minded. Asking personal questions is a great way to learn more about someone else’s experiences and viewpoints. Try to keep an open mind when you hear their responses, even if you disagree or don’t understand where they’re coming from. You’ll probably learn something you didn’t know!
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