The best collection of Icebreaker Questions you’ll ever need

Questions are crucial when it comes to building a strong relationship.  

Asking Icebreaker questions is one of the admirable ways to get closer to someone. Your questions will say whether you really care about that individual or not.

Sharing good topics for Conversation starters helps them feel comfortable with you, and when they talk more about themselves, you’ll have an easier time finding common interests and connecting with them.

But asking the right questions at the right time can also help your networking efforts. 

Wondering what questions to ask in order to build relationships? This article will walk you through how to ask questions in order to build a stronger network and more meaningful connections.

This list of Icebreaker questions covers many situations, such as dating, building friendships or love; workplace, or even for kids and students who want to increase their circle.

Recommended read: 250 Questions to ask to understand anyone

Icebreaker Questions

The following is a huge list of icebreaker questions for any social situation:

What is the coolest thing you have ever done?

What is one thing you have never done before?

What’s a big milestone you want to achieve in the future?

What was the most recent book you read?

If you were a brand of car, which would you be and why?

What’s something that you’re really good at that you normally don’t receive any recognition for?

What is your favorite childhood memory?

What is the most valuable lesson you have learned in the last year?

What was your most embarrassing moment?

How do you feel about the weather in Anaheim?

What aspect of your life has changed the most in the last year?

Favorite thing to do on the weekend?

What do you think about the movie “The Martian”?

Is there anything you would like to share with everyone?

What’s the most awkward situation you’ve been in with a complete stranger?

Also read: 100+ questions to ask people to get to know them

Funny Icebreaker Questions

Here is a list of funny icebreaker questions:

If a tree falls in an exceedingly very forest & nobody is around to pay attention thereto, does it still make a sound?

Why can we press harder on a foreign control once we all know the batteries have become weak?

If quizzes are quizzical, what are tests?

Why should I put your two cents in, but it’s only a penny for your thoughts?

Once you’re in heaven, do I hamper wearing the clothes you were buried for certain eternity?

Why do people pay to travel up tall buildings, then put money in binoculars to look at things on the ground?

Why is it called ‘after dark’ when it really is ‘after light’?

If you’re in an exceedingly vehicle going the speed of sunshine, what happens once you activate your headlights?

Why do people pay to travel up tall buildings so put money in binoculars to seem at things on the ground?

If nothing ever sticks to TEFLON, how do they create TEFLON to continue with Teflon?

Best Icebreaker Questions

What is one thing you would like to change about your life?

What would you do if you won the lottery?

What is your favorite comic strip?

What is a book you read that has had the biggest impact on your life?

When was the last time that you cried?

What do you think is the most important thing about being a good person?

What does being a good person mean to you?

What do you think is more important in life: Love or wealth?

What is the biggest issue you face in your life right now?

What would your friends say is your best quality?

What motivates you?

What is the best way to spend a day off and why?

What’s something that you like to do that most people don’t know about?

What is your best work experience?

What makes you angry?

Icebreaker Questions for adults

If you were to have a conversation with the person sitting across from you (who you don’t know yet), what would you ask them?

What is the nicest thing anyone has done for you?

What is one thing most people don’t know about you?

What is the best way to get to know someone?

What do you think is the most important skill to have in order to be successful and achieve your goals?

What is one thing you hate about yourself?

What is the best part of being married to [name]?

If you had the opportunity, what city would you and your partner most like to visit?

What is the first word that comes to mind when you think about your partner?

How is your relationship going on?

Have you ever cheated on your partner?

What’s a healthy relationship?

Have you found your purpose in life?

What are your future plans for career, marriage, and lifestyle?

Do you have any interest in starting a business?

What is something you’ve done that was really hard for you?

Who is a good friend of yours?

What is your favorite thing about yourself?

How long have you known each other?

What is your favorite restaurant?

What is the first thing you do after you get up in the morning?

What did you want to be when you were a kid?

Have you ever been in a situation where you didn’t know what to do to help someone?

What is your idea of a perfect date?

Icebreaker Questions for teens

What does a good friend mean to you?

What’s your favorite thing to do on a date?

What’s the best conversation you’ve had with a stranger? What made it great?

Do you have a crush on anyone?

Have you ever lied to your parents?

What’s something you have done without telling your parents?

If you could sit down with any person, who would it be?

What are your 3 best qualities?

What is the most interesting thing you have done in your life?

What are 3 things you are most grateful for?

How old is your oldest friend?

What is the most common stereotype you face in your profession?

What do you think about when you’re alone?

What is a fun fact about yourself?

What is something that you wish you knew when you were younger?

What’s the weirdest thing you’ve ever eaten?

What are the best books you have read in the past 6 months?

Great Icebreaker Questions

Here is a list of great icebreaker questions:

How do you make a decision when you have to choose between two things?

What is the best way to spend your free time?

What were the most important events in your life that shaped you into who you are today? How did they effect you?

What are 5 things you would like to do before you die?

Do you believe that growing up in a particular country or culture influences your moral values?

If you were to write a book about your life, what would it be named?

What has influenced your morals and values the most?

What do you think is the most important thing to teach children?

Do you have any moral values that guide your decisions?

What is an example of a time you had to make a really hard decision?

Did you have any mentors when you started college?

What is the best advice you have ever gotten?

How do you define success?

What was the most memorable time you spent with your family?

Good Icebreaker Questions

What are your thoughts on life?

What qualities do you find important in a best friend?

What do you value most in life?

What is one thing you think everyone should try at least once?

What are your core values?

How do you define life?

What philosophy would you recommend to our readers?

What is the best decision you have made in your life?

Who are you? What drives you? What do you enjoy in life?

Do you have a philosophy or life outlook that guides your work?

What are some of the different things that make you who you are?

What are your morals and values?

What is the silliest thing you have ever done?

What is a fun fact about you?

What is your dream job?

What is your biggest weakness?

What was the last movie you watched with your family?

Who is your favorite author?

Interesting Icebreaker Questions

What is the best moment you have had that influenced your life?

If you could ask the person on your right anything, what would it be?

What are your hobbies?

If you could go back in time, what advice would you give to your early self?

If you were an ice cream flavor, what would you taste like?

If you were a fruit, what type of fruit would you be?

What is something unique or weird about you?

Is there anything you want to start doing but haven’t started yet?

If you could choose the place and time of your birth again, where and when would you be born?

What is the best movie you have ever seen and why?

If you could only keep one of the following: your job, house, car, or cell phone which would you keep?

What is the most memorable ice breaker game you’ve played?

If you could pick one person to run a 1-mile race against, who would it be?

Deep Icebreaker Questions

What is it that makes life worth living for you?

How do you decide what is morally right?

What is your personal philosophy?

What is the best way to live a morally good life?

What one person has been the biggest influence on your life?

Do you feel there is a right or wrong in life? If so, what is it?

How can you tell someone’s personality?

What do you think is the most important aspect of life?

What do you consider to be the best life lesson?

Also read: 100+ Deep Icebreaker Questions

Unique Icebreaker Questions

If you were sitting on a cloud and could ask any three people, living or dead, to join you, who would they be?

What do you think the meaning of life is?

What is one thing you have learned from a friend?

If you could ask any person in the world one question what would it be?

What do you think are the most important lessons in life?

What makes you happy?

What is an example of a moral dilemma you have faced?

What is your biggest accomplishment?

What’s something you do that makes life more enjoyable?

What is your biggest regret in life?

What is the most important thing to you?

Random Icebreaker Questions

What is the strangest thing you have ever eaten?

Do you have a personal philosophy?

How would you describe yourself? What is your greatest strength?

What was the best vacation you have ever taken?

What do you think is the best thing about yourself?

How do you maintain friendships with peers?

What are some things that make you happy?

What do you like most about your job?

What is the best vacation you ever had?

What is your favorite kind of cheese?

What is the last thing you ate?

Weird Icebreaker Questions

If you could ask the President of the United States 1 question, what would it be?

If you could only eat one type of food for the rest of your life, what would it be?

If you could be a superhero, what would your superpower be?

Who’s the most famous person you’ve ever met?

What was your favorite high school class?

If you could only take 3 things to a deserted island, what would they be? Now the same question but for work?

Do you have any holiday traditions?

If you could go anywhere in the world for vacation tomorrow, where would you go?

If you had to pick a superhero or celebrity to join your business, who would it be and why?

How do you two compare to each other in terms of personality?

What was going on in your life that made you want to date?

If you could go anywhere in the world with your partner, where would you go?

What’s a fun fact about yourself?

Icebreaker Questions for students

What was your most memorable childhood toy?

What’s the first thing you do when you get home from work?

What was your favorite subject the first year of school?

Where do you usually go to have fun?

What is in your refrigerator at this very moment?

What is the last thing you purchased?

What is your favorite type of music and why?

What was your favorite tv show as a kid?

What do you want to be when you grow up?

What is your favorite video game?

What is your favorite childhood memory?

What is the best lesson you have learned from your parents?

What is your favorite subject at school?

What number of siblings do you have?

How would you describe your childhood?

Did you do anything fun in the last week?

What is the last book you read that was not for class or work?

What do you want to be when you grow up?

What things have you done in the last year that you would not have done had it not been for this class?

Christmas Icebreaker Questions

What is your favorite christmas tradition?

What was Christmas like when you were a child?

What do you like most about Christmas?

What is your favorite Christmas movie?

How do you feel about the Christmas holiday?

What’s your favorite Christmas movie?

Do you like christmas?

What is your ideal christmas?

How did you spend Christmas last year?

What is your favourite Christmas memory?

What does Christmas mean to you?

What has been the best part of your Christmas break?

Do you believe that there is a Santa Claus?

What do you want for Christmas?

What is the most memorable Christmas gift you have ever received?

What is the funniest or most embarrassing Christmas gift you have received?

What do you look forward to doing this Christmas?

What was the most memorable holiday (Christmas, Thanksgiving, etc.) you have had?

What would be your ideal Christmas gift?

What Christmas tradition do you look forward to the most?

What is the best part about your holiday?

What is your favorite piece of holiday decor?

Icebreaker Questions for couples

Is there anything you want to ask me? What questions do you have?

What was your first date like?

What was the grossest thing you ate as a kid?

What would be your ideal day?

Where did you go on your first date?

When did we meet for the first time?

What is the worst gift you have ever received from me?

How do you deal with conflict with me?

Who has more patience?

What is some advice you have for any newly engaged couples?

What are you looking forward to tonight?

If you could only choose one for the rest of your life, would it be money or love?

If you were to start a company with your partner, what would it be?

How would you define love?

What is the last thing you did together?

How would you describe your dating life?

Have you ever been in an arranged marriage?

What are your favorite romantic date ideas?

Where is the most random place you’ve kissed?

Where is the most romantic city in the world?

What do you like to do together?

If you had to pick one, who would be the driver, and who would be the navigator when you two are traveling together?

How would you describe your partner?

What is your favorite quality in your partner?

Can you still remember your first kiss?

What is your ideal date?

What was the most interesting thing you’ve learned about your partner?

What is your relationship like?

Icebreaker Questions for friends

How do you feel about your life right now?

What are your top three favorite movies?

What is the best way to learn something new?

What is your hidden talent or hobby?

How did you learn to drive? Or, How did you get your driver’s license?

What is the best advice you have ever received?

What do you prefer: dogs or cats?

What is your favorite icebreaker question to ask someone new?

What’s the worst job you’ve ever had?

What is the best part of living in New York City?

If you had to describe your personality in 3 words, what would they be?

What’s a question you’ve always wanted to ask someone?

What is the best advice a teacher has ever given you?

What do you value most in a friend?

What are your favorite dishes and foods?

What is your favorite topic of conversation?

What are the top 3 things you’d change about yourself?

Would you rather Icebreaker Questions

Would you rather live alone or spend the rest of your life with the wrong person?

Would you rather sleep early or wake up early?

Would you rather love yourself or love others?

Would you rather be the first in everything or don’t care for anything?

Would you rather make more money and give for charity or spend on costly materials?

Would you rather do what you love or try hard to do on something that you don’t like?

Would you rather kiss or hug?

Would you rather be a human or god?

Would you rather start something early or wait for the perfect time?

Would you rather work for someone or start your own company?

Quick Icebreaker Questions

What is your favorite book of all time?

What do you want to be when you “grow up?”

How do you feel about the way your life is turning out?

If you could do anything differently in your life, what would it be?

If you could have dinner with any person in history, who would it be?

What is something you know now that you wish you

What is the most interesting photo on your phone?

What is your favorite quote?

What’s the most satisfying moment in your life?

What is something everyone should try before they die?

If you could change one thing about yourself what would it be?

You have the power to change one thing about your life. What would it be and why?

Easy Icebreaker Questions

What is your favorite movie?

What is your favorite song?

What was your first car?

What is your favorite ice cream flavor?

What’s your favorite word?

What is your favorite food?

What is something you’ve wanted to do for a long time, but haven’t?

What is the most fun you’ve had in the last week?

What is your favorite form of exercise?

What is your favorite fruit?

Silly Icebreaker Questions

If you could be a fictional character, who would it be and why?

What is the best book you ever read?

What was the best thing you did last year?

What is your favorite band?

What are 3 things you like to do in your free time?

Where is your favorite place to relax?

If you could go back to your middle school self and give yourself one piece of advice, what would you say?

What is your favorite food or restaurant?

What is your favorite place to eat?

How do you think your personality has changed since high school?

What is something you are good at?

How has your life changed in the last year?

How did you feel when you first met me?

What kind of music do you like?

Holiday Icebreaker Questions

What is your favorite holiday activity?

What is the best holiday you’ve been on?

What is your favorite holiday and why?

What was one of the best holiday experiences?

What were the best and worst holiday gifts you’ve ever received?

What was the most recent vacation you have been on?

What have you done this week that you are most proud of?

What are your favorite things to do on the weekend?

What is your ideal vacation?

How do you make friends while you travel to new places?

Icebreaker Questions for work

What are some of your work-related hobbies?

What is the hardest part of your job?

If you were to start your own company, what would you do?

How did you come up with the idea for your company?

What is your most memorable experience at work?

What are some positive changes you have seen in your workplace in the past year?

What is the most exciting thing you are working on right now?

How did you get into your career?

What is the best part of your job?

What are your favorite and least favorite things about working at [Company name]?

If you could ask your boss one question, what would it be?

What is the biggest surprise you’ve had since you started working on this company?

What’s your favorite thing about working in the tech industry?

Do you have any friends that are entrepreneurs?

What is your favorite part of the interview process?

What is your job title and responsibilities?

How would you introduce yourself at a networking event?

What is the best work you’ve ever done and why?

Team building Icebreaker Questions for work

Which books would you recommend to someone starting a business?

Are you more afraid of making decisions or giving bad news?

In your opinion, what is the most important trait of a good leader?

What are some of the biggest challenges you face on a daily basis while working with the team?

What is the most awkward work situation you’ve been in with your co-worker and how did you handle it?

As a group, what is something we can do to ensure that we feel comfortable with one another?

What do you do differently to inspire your team and work together more efficiently?

What can you tell me about your business that I may find interesting?

What do you make of the atmosphere in your office?

Which do you enjoy more: a fun work environment or a busy work environment?

What is a question that you are always asked at work or by your peers?

What is your work ethic?

What is something you do that makes you more productive?

Do you have any advice for other entrepreneurs?

Where do you see yourself professionally in the next 5 years?

Name a person who has had a significant influence on your career.

How do you feel about your business idea?

What is the best thing about working at Two Day Startup?

What is your favorite non-business related hobby?

Small group Icebreaker Questions

What are you most passionate about?

Who is the last person you called?

What is the last thing you bought online?

What is your favorite type of music?

What would your best friend say about you?

What is your favorite date spot in the city?

What is the best part of being an entrepreneur?

What’s a fact about each other that the other person doesn’t know?

What is your favorite vacation spot?

Have you ever broken up with someone and later regretted the decision? Explain.

What is your favorite thing about each other?

What do you think is the difference between men and women?

Do you consider yourself an introvert or extrovert?

How have I influenced your life?

Where is the most romantic place you have ever been?

What are your favorite television shows?

What is something you learned from your parents?

If you could choose the name for your first child, what would it be?

What’s your favorite way to start a conversation with a stranger?

What trait do you find most attractive in your significant other?

What is the most romantic thing you’ve ever done for your partner?

Have you ever met anyone famous?

What’s the best birthday gift you’ve ever received?

How do you feel about the other person’s answers to these questions?

What is your favorite activity to do outdoors?

Pic Credits

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