125+ Witty, Clever & Impressive Icebreakers

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Creative questions to start conversations

Co-authored by Dev Murphy, MA Reviewed by John Keegan

Last Updated: February 9, 2025 Fact Checked

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Qs for Friends

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Qs for Partners

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Deep Qs

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Qs for Alexa

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Using Humor to Foster Intimacy

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Wit vs. Humor

Want to entertain your friends with your wit and charm—while also learning more about them? These witty questions, from the more surface-level to the more serious, are sure to have your friends cracking a smile or even a laugh at your cleverness. Plus, stick around to learn how humor can help you grow closer to your friends and loved ones.

Best Witty Questions

If you could be any age for the rest of your life, which would you choose?
Why are turtles green?
What’s the most random thing in your fridge right now?
What’s the weirdest habit you have?
Can you fold a fitted sheet by yourself?

Section 1 of 6:

Witty Questions to Ask Friends

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Ask your BFFs these clever questions to crack a smile. Your friends know you better than anyone, so you might feel like it’s tough to surprise them at this point—that’s where you’re wrong! These witty icebreakers are guaranteed to take them by surprise.
- Which celebrity would you choose for your best friend?
- If you could only wear one color for the rest of your life, which one would you choose?
- What’s your go-to breakfast order?
- Why are turtles green?
- What’s your favorite playlist?
- What’s a hidden talent that you’ve never had a chance to show off?
- What’s the weirdest thing you’ve done to save time or effort?
- Which color has the worst personality?
- What is your go-to shower song to sing?
- How late is too late to cancel a plan with someone?
- Hiking or video games?
- Why do cats have nine lives?
- What is one thing you think is really overrated?
- If you could get rid of one veggie immediately, which one would you choose?
- What’s your favorite nickname you’ve been given?
- If rainbows could talk, what would they sound like?
- What world record do you think you could break?
- What’s something about me that annoys you?
- Which Disney character is the most annoying?
- What’s the weirdest gift you’ve ever received?
- What’s the cringiest fashion trend that you still follow?
- Which Disney character would you least like to dress up as at Disney World?
- What’s the dumbest way you’ve ever hurt yourself?
- Who is your style role model?
- What is your least favorite sound?
- Do you drink or eat soup?
- What do you think the most unpleasant sound is?
- What was the best meal you’ve ever eaten?
- What would your drag name be?
- What’s a weird smell that you really enjoy?
- What’s the most outrageous lie you’ve ever told?
- What’s your favorite conspiracy theory?
- What’s the strangest dream you’ve ever had?
- What’s the longest amount of time you’ve been away from home?
- How long would you last in The Hunger Games?
- What’s a word that you always have trouble spelling?

Section 2 of 6:

Witty Questions to Ask Your Boyfriend or Girlfriend

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Keep the spark alive by asking these charming icebreakers. Whether you’ve been dating for two months or 10 years, there’s always more to learn about your partner. Whip out one of these clever get-to-know-you questions to share a giggle and foster intimacy:
- Which celebrity would you break up with me for?
- Would you still like me if I was a worm?
- What’s the most random thing in your fridge right now?
- What gives you the ick?
- What’s the most unusual job you’ve ever had or heard of?
- How did you get yourself out of an embarrassing moment and what happened?
- If you could only listen to one song for the rest of your life, what would it be?
- What’s the funniest thing that’s happened to you recently?
- What’s one time I looked absolutely foolish?
- Is charcuterie a meal?
- What’s the most embarrassing thing someone has walked in on you doing?
- What’s a food combination that you love but others might find strange?
- What’s the weirdest habit you have?^{[1]
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- If you could switch lives with any celebrity for a day, who would it be?
- What’s the most unusual pet you’ve ever had or wanted to have?
- If you could only eat one snack for the rest of your life, what would it be?
- If you could instantly become famous for something silly, what would it be?
- Can you fold a fitted sheet by yourself?
- Would you rather speak in rhymes or speak with a different accent every day for the rest of your life?
- If you had to eat a crayon, which color would you choose?
- What’s one thing you’ll never do again?
- Would you rather have hands for feet or feet for hands?
- Would you rather have hair for teeth or teeth for hair?
- If you could name a new state, what would it be?
- Which role would you play in a reality TV show?
- Which fruit would you be and why?
- Can you touch your tongue to your nose?
- What’s one thing everyone looks silly doing?
- What’s the weirdest date we’ve ever been on?

Section 3 of 6:

Witty Deep Questions

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Humor can help you take a conversation even deeper. You might not think a silly icebreaker can help you get to know someone on a deeper level, but actually, humor is a great way to segue into more serious conversations. Why? It loosens everyone up and fosters trust between you, so people tend to feel more comfortable sharing.^{[2]
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Research source} Try using one of these witty icebreakers to get the conversation flowing:
- How do you think your friends describe you?
- What’s the last TV show you binge-watched?
- What’s a phrase or saying that you tend to overuse?
- Is there a daily routine you follow that others might find unusual?
- What’s the most unusual item you keep on your nightstand?
- What’s the most surprising thing someone would find out about you?
- If you could be any age for the rest of your life, which would you choose?
- Do you think the internet can actually be broken?
- If you could design your own amusement park, what would be its theme?
- Would you switch lives with me for a day?
- Do you have any superstitious beliefs that you secretly follow?
- Is the glass half empty or half full?
- What’s the funniest thing you’ve ever done on a dare?
- What was the best gift you ever received?
- If you could have anything in your pocket that’s completely impractical in emergencies, what would it be?^{[3]
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- What do you think the quickest way to turn around a bad day is?
- If you could make up a future job title for yourself, what would it be?
- What’s the most unbelievable thing about you?
- Which reality star would you pick to officiate your wedding?
- What is something you can’t give up?
- What warning label would you give for your life?
- What’s the worst book you’ve ever read?
- Have you ever completely misunderstood song lyrics?
- Are you adventurous?
- Who is your biggest fan?
- What do you notice first about another person?
- Personal uniforms or a different outfit every day?
- Who would you pay the most money to see in concert?
- Who was your favorite teacher and why?
- What was your favorite toy growing up?
- Who was your first celebrity crush?
- Do you think animals and humans have a special connection?
- What is your favorite piece of advice?
- Did you ever have a crush on an animated character?
- Have you ever seen a ghost?
- What is one thing you think can’t be explained?
- What is a silly thing you take a lot of pride in?
- Have you ever won an award?
- What’s the biggest coincidence you’ve ever witnessed?
- How do you think the world is going to end?

Section 4 of 6:

Witty Things to Ask Alexa

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You don’t need friends around to have fun with silly questions. While away the hour asking Alexa witty questions. We’ll do our best to stump her!
- What came first, the chicken or the egg?
- Will you tell me a limerick?^{[4]
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- Will you roast Tom Brady?
- Why did the chicken cross the road?
- Will you tell me a tongue twister?
- Will you beatbox for me?
- Who is your celebrity crush?
- Will you self-destruct?
- Do you have any pets?
- Are you married?
- When is your birthday?
- Can you tell me a fun fact?
- Can you guess what number I’m thinking of right now?
- How do you like to relax or unwind after a long day?
- What’s your favorite food?
- Have you ever been fired?
- What’s your favorite fact?
- What is your pet peeve?
- Where do you want to go on vacation?
- What do you like about me?

Section 5 of 6:

Using Humor to Foster Intimacy

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While the questions above might seem like all fun and games, it’s usually through fun and games that we get to know friends and loved ones better and cement our bond. Laughter loosens us up and persuades us to lower our defenses, making deeper, more intimate conversation come more easily.^{[5]
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Trustworthy Source

Greater Good Magazine
Journal published by UC Berkeley's Greater Good Science Center, which uses scientific research to promote happier living

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Section 6 of 6:

What’s the difference between “witty” and “funny”?

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When someone says something clever or witty, they likely impress you with their sharp intellect or delight you by inviting you to look at something in a surprising way. When someone is funny, on the other hand, humor is more often an emotional reaction to their behavior, rather than a mental one.^{[6]
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