Break the Ice With These 150 Fun Check-In Questions

Say more than “How are you?” to your team and loved ones!

Co-authored by Alexandra Friedman and Aly Rusciano

Last Updated: December 11, 2025 Fact Checked

For Your Team

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For Kids

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For Anyone

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Quick

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Mental Health

Need to break the ice with a coworker, friend, or kid? Well, you’ve come to the right place! There are hundreds of questions you can ask to check in on someone and learn more about them. In this article, we’ll share our favorite icebreaker questions for any situation. Plus, we even threw in a few tips from clinical psychologist Lena Dicken, PsyD, and communication coach Cristina Morara on how to say more than “How are you?”

Fun Icebreaker Questions

What’s the most used emoji on your phone?
What’s your go-to karaoke song?
What kind of music do you listen to while working?
What’s your favorite drink?
If you could have a superpower, what would it be?

Section 1 of 5:

Fun Check-In Questions for Your Team

Get your team motivated with these fun questions. A simple icebreaker can go a long way during a team call or meeting! Warm up the space with one of these questions to see how everyone’s doing. Not only is an opening check-in question a great way to get everyone talking, but it can also help you learn more about your coworkers and promote team-building!
- What’s your go-to coffee order?
- What is your goal for today?
- What do you hope is for lunch today?
- How has your day been so far?
- If you could time-travel, where would you go?
- If you could learn any secret, what would it be?
- Show us something interesting in your office.
- Have you heard a good joke lately?
- What’s one random fact about you?
- What’s an underrated skill you have?
- What color best describes you?
- What are you excited about this week?
- What book has inspired you most?
- Share a productivity hack.
- What are you grateful for today?
- What’s something that’s made you smile today?
- What’s something you can’t live without?
- What fruit represents your mood today?
- What song represents your workday so far?
- What life hack has improved your life?
- What’s something you want to be better at?
- Do you have a favorite mug or water bottle?
- Do you work better with or without music?
- What food best describes our team?
- Which emoji represents you today?
- Name a TV show you think is underrated.
- What do you like to do in your free time?
- What profession do you think you’d have in another life?
- What flavor of tea represents you today?
- What’s a fun fact that blows your mind?
- What kind of music do you listen to while working?
- What’s the most used emoji on your phone?
Meet the wikiHow Experts

Lena Dicken, PsyD, is a clinical psychologist who specializes in anxiety, depression, and life transitions.

Cristina Morara is a communication coach who specializes in relationships.

Section 2 of 5:

Fun Check-In Questions for Kids

Ask kids these questions to spark a fun, imaginative conversation. Maybe you’re a teacher looking for fun questions to ask your students, or perhaps you're trying to keep a younger sibling entertained. No matter the reason, these ice-breaker questions are perfect for kids—they’re imaginative, creative, and simply goofy!
- What’s your favorite ice cream flavor?
- Do you have any hidden talents?
- What do you like to do on a rainy day?
- If you could have a superpower, what would it be?
- What’s your favorite movie?
- Who’s your favorite superhero?
- What’s the silliest thing you can think of?
- What’s something that always makes you laugh?
- What would you do if you could be invisible for a day?
- If you could go anywhere in the world, where would you go?
- What movie would you want to live in?
- If you were famous, what would you be famous for?
- What would you do if you won a million dollars?
- What famous person would you invite over for dinner?
- Would you rather have a pet dinosaur or a pet dragon?
- Would you rather be a princess or a mermaid?
- What would you do if it started raining meatballs?
- If you were an emoji, what emoji would you be?
- What would a TV show about your life be called?
- If you were president, what’s the first thing you would do?
- Would you rather meet a robot or an alien?
- What is your favorite book?
- What’s the weirdest thing you’ve ever eaten?
- Do you know any good jokes?
- If you could have any other name, what name would you choose?
- What would you do if you could time-travel?
- What do you want to be when you grow up?
- Would you rather be able to fly or turn invisible?
- Would you rather have a magic wand or a flying broomstick?
- Who is your favorite person?
- Looking for more kid-friendly icebreaker ideas? Check out “Awesome Icebreakers for Work, Adults, Teens & More”!

Section 3 of 5:

Fun Check-In Questions for Anyone

Ask anyone these icebreakers to start a conversation. Whether you’re meeting someone new or chatting with a close friend, chances are you’ll learn something new with one of these questions! Morara suggests “asking the question that you would like to be asked.”^{[1]
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Expert Source

Cristina Morara
Communication Coach

Expert Interview} For example, you could try to find a common interest and start a conversation from that. These check-in questions are fun and help break the ice in practically any situation:
- What’s your favorite board game?
- What was your first job?
- What’s your dream car?
- What’s your favorite pizza topping?
- What’s your least favorite sport?
- What’s your go-to karaoke song?
- What song must you sing in the shower?
- What’s your favorite children’s book?
- Who’s your favorite artist?
- What’s your lucky number?
- What’s your favorite food?
- What’s your favorite way to eat potatoes?
- What’s your signature dance move?
- What would you like an unlimited supply of?
- What’s your favorite drink?
- What’s your favorite joke?
- What would be your personal theme song?
- What’s the best gift you’ve ever received?
- Do you prefer coffee or tea?
- Would you rather vacation in the mountains or on the beach?
- Are you an early bird or a night owl?
- Would you rather go to a concert or a museum?
- Do you prefer cats or dogs?
- What’s one thing you’ve always wanted?
- Tell me a surprising, fun fact about you.
- What’s your best childhood memory?
- What would the title of your memoir be?
- Who would play you in a movie?
- What movie describes your life?
- If you were an animal, what animal would you be?
- What’s your favorite way to waste time?

Section 4 of 5:

Quick Fun Check-In Questions

Use these quick questions for a spontaneous ice breaker. Need to fill an awkward silence? Spark a conversation with a friend, coworker, or even stranger with one of these quick this-or-that questions—they’re spontaneous, witty, and creative:
- Dog or cat?
- Book or movie?
- Coffee or tea?
- Chocolate or vanilla?
- Introvert or extrovert?
- Comedy or drama?
- Spicy or mild?
- City or country?
- Apply or banana?
- Sneakers or sandals?
- Ducks or geese?
- Concert or museum?
- Pancakes or waffles?
- Salt or pepper?
- Card game or board game?
- Ice cream cone or cup?
- Salsa or guacamole?
- Taco or burrito?
- Juice or soda?
- Sweatpants or jeans?
- Long sleeves or short sleeves?
- Sunglasses or hat?
- Beach or mountains?
- Ribbons or bows?
- Outer space or the sea?
- Science or magic?
- Earbuds or earphones?
- Apple or Android?
- DC or Marvel?
- Pepsi or Coke?

Section 5 of 5:

Mental Health Check-In Questions

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See how a loved one is doing with one of these questions. Sometimes, you want to see how someone is but want to say more than “How are you?” The questions below are great ways to inquire about someone’s mental health, emotions, or life with care and compassion:
- What’s shaking?
- What’s something you’re looking forward to?
- What’s at the front of your mind?
- What’s the vibe today?
- What did you do today?
- What have you been listening to lately?
- Did something make you smile today?
- What are you feeling right now?
- What’s your day been like so far?
- Is there anything you need right now?
- What did you do today?
- What’s something you’ve been enjoying lately?
- How’s your heart today?
- Long time no see!
- What’s been on your mind lately?^{[2]
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  Research source}
- What word would you use to describe your life right now?
- What question do you wish someone would ask you right now?
- How have you been sleeping?
- What’s one nice thing you did for yourself today?
- Thinking of you!
- What’s up?
- I hope you’re doing well!
- How’s your week going?
- How’s work?
- What’s new?
- It’s been a while!
- How’s it rolling?
- What’s going on?
- Did you do anything fun today?
- Do anything exciting this weekend?
- How’s life?
- Hoping you’re well!
EXPERT TIP

Lena Dicken, Psy.D
Clinical Psychologist
Dr. Lena Dicken is a Clinical Psychologist based in Santa Monica, California. With over eight years of experience, Dr. Dicken specializes in therapy for anxiety, depression, life transitions, and relationship difficulties. She utilizes an integrative approach combining Psychodynamic, Cognitive Behavioral, and Mindfulness-based therapies. Dr. Dicken holds a BS in Integrative Medicine from the University of Hawaii at Manoa, an MA in Counseling Psychology from Argosy University Los Angeles, and a Doctor of Psychology (Psy.D) in Clinical Psychology from the Chicago School of Professional Psychology at Westwood. Dr. Dicken’s work has been featured in GOOP, The Chalkboard Magazine, and in numerous other articles and podcasts. She is a licensed psychologist with the state of California.

Lena Dicken, Psy.D
Clinical Psychologist

It’s okay to be a little more blunt when checking in with a close loved one. Try saying something like, “How have you been emotionally?” “What have you been feeling lately?” or “Are your feelings related to the current state of the world?”
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The best way to support others is to be reassuring and patient. Whether you’re chatting with a friend or coworker who’s struggling, remember to always listen, offer reassurance, and be patient.^{[3]
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Expert Source

Alexandra Friedman
Friendship and Connection Coach

Expert Interview} They may not be willing to open up right away, and that’s okay! Inquiring about how they are and showing an interest in them can help pave a path for a deeper connection.^{[4]
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Trustworthy Source

Mind
U.K.-based mental health charity focused on providing advice and resources to anyone facing mental health problems.

Go to source}
- Dr. Dicken says that people often “feel safer to open up once you’ve opened up.” So, don’t be afraid to discuss your feelings too, if the moment feels right.^{[5]
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  Expert Source
  
  Lena Dicken, Psy.D
  Clinical Psychologist
  
  Expert Interview}