Top 101 Funny Conversation Starters with Crush to Win Heart

Filed in Articles by on November 2, 2021 0 Comments

Funny Conversation Starters

Funny conversation starters are one of the most powerful tools you can have. Because if there were one skill every person worried about their conversation abilities would want to have, it would be humor. We have lots of words for it, all of them positive: “charm” and “wit” used by a “clever” or “amusing” person.

No matter what you call it, though, being funny is a great way to meet people, become successful, and generally get what you want.

But what most people don’t know is a lot of the work involved in being funnily canned comes down to simply choosing the right conversation questions to ask.

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Having the right conversation starters gets you halfway to being that charming, amusing person everyone wants to have a chat with.

If you have a few funny questions to ask ready at hand, you’d be surprised how quickly a great conversation can startup, and just how funny you and others can be once you have the opportunity.

101 Funny Conversation Starters with Crush

Take a look at these 101 funny conversation starters with crush to win heart

  1. What Would A World Populated By Clones Of You Be Like?

Is it the more of you the better or would you get sick of seeing yourself after the third clone? Find out how much your conversation partner loves themselves.

  1. What “Old Person” Things Do You Do?

Prunes every morning or Matlock marathons: no matter what the answer is it’s sure to lead to a few half-embarrassed chuckles.

  1. What Did You Think Was Cool When You Were Young, But Isn’t Cool Now?

This is an opportunity to indulge in a little nostalgia that’s also a little self-deprecating. Think of all the trends that seem ridiculous in retrospect: acid-washed jeans, mullets, flannel shirts. There are lots to work with.

  1. If You Could Have Your Own Reality TV Show, What Would It Be?

Here’s a chance to be amusing and creative at the same time. Pick out the most ridiculous points in popular reality shows and construct your own. Then imagine how it would play out.

  1. If You Were In A Witness Protection Program, What Would Be Your New Name And Where Would You Go?

Innocent McNobody or Gerald Fingerpointer: the options are limitless and limitlessly amusing. There’s also an opportunity to dream about the perfect place to settle and perfect life if you had to start all over.

  1. Which Of The Seven Dwarfs Is Most Like You?

Are you more a Sleepy or more a Happy? Maybe you should come up with an Eighth Dwarf: Hungry or Awkwardy.

  1. What’s The Best Wifi Name You’ve Ever Seen?

A little like the witness protection question above, but now you’re basing answers on actual experience. If you’re in a crowded area, you could surf around for results right there.

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  1. If You Were A Candy Bar, Which Candy Bar Would You Be?

Are you nutty as a Snickers or smooth as the caramel in a Canbury Cream Egg? Maybe you just need a break like a Kit-Kat.

  1. How Long Would You Last In A Zombie Apocalypse?

Everyone always imagines they’re among the survivors in zombie movies, but how long would you actually last? This can open up a lively debate in a group in order to reach a consensus on who would last the longest.

  1. What Would Be Your Weapon Of Choice?

If those zombies were coming for you, how would you defend yourself? Sure, most people would go for the easy answers like semi-automatics and grenade launchers, but you know someone would go all out in medieval knight armor and broadsword.

  1. Would You Like A World With Magic In It?

What would the world really be like with magic? Here’s your chance to imagine yourself in your favorite fantasy book or show, while also considering the real consequences.girl reading a book that shines when opened

  1. If You Were Given One Thousand Acres Of Land, What Would You Do With It?

Are you the farmer type or have you always wanted to play cowboy? Or, would you take all that land and build a top-secret base for your own secret purposes?

  1. If You Could Hack Into Any One Computer, Whose Computer Would You Choose?

Whose secrets do you really wish you knew? Your conversation partners might go for the most powerful people (presidents and business leaders), or they may just wish they knew what their ex- was doing.

  1. If You Built A Themed Hotel, What Would The Theme Be And What Would The Rooms Look Like?

Another very creative and funny conversation starter where you can build up a whole hotel that either reflects a passion (say, a favorite show or book series) or else something really bizarre (any takers for cheeses of the world-themed hotel?).

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  1. Would You Rather Never Use Social Media Sites/Apps Again Or Never Watch Another Movie/TV Show?

Just how important is social media to your conversation partners? Their difficulty in making this choice will give you a good idea of the answer.

  1. If You Could Have Dinner With Any, Currently Alive, Person In The World, Who Would It Be?

A bit less intrusive than hacking someone’s computer. This is a fun way to ask someone who is the most interesting person alive.

  1. What Would You Do With An Extra $1,000 To Spend Only On Yourself?

The answers to this one can span from the genuine or obvious (pay some debt, buy a new gaming system) to the amusing (fill the pool out back with Jell-O).

  1. If You Could Master Any Instrument On Earth, What Would It Be?

Discussing music is one of the best ways to get to know someone. An even better way, find out what instrument your partner wishes they played, then suggest you learn how to play it together.

  1. Would You Rather Have A Live-In Massage Therapist Or A Live-In Chef?

One of the best conversation starters for couples because it’s actually a sneaky way to find the hidden key to your partner’s heart. Is a massage or a nice meal the get out of jail free card in your relationship?

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  1. What’s A Movie You Can Practically Quote From Start To Finish?

This question is the best way to cheat and find the perfect movie for your next date night. Then, have fun quoting the whole thing together.

  1. Who Would Play You In A Movie About Your Life? Who Would Play Me?

Ask this question if you dare, and hope your partner sees you as one of Hollywood’s hottest and not one of its amusing trolls!

  1. If You Could Go Back In Time And Make Little Changes To Your Childhood, What Is One Thing You’d Learn And Master Over The Years So You’d Be An Expert At It Today?

Find out what your partner really, secretly wishes they could do. Do they dream of playing the piano or being a professional athlete? This question could allow you to help them reach some important goals, and also leaves room for some silly responses.

  1. If You Could Choose To Stay A Certain Age Forever, What Age Would It Be?

Were the glory days at age 18 or 25? Or, does your partner think they’re still ahead? Learn to live like your best age together and enjoy discussing old memories.

  1. Would You Rather Have An Easy Job Working For Someone Else Or Work For Yourself But Work Incredibly Hard?

The balance between work and independence is a tricky one, but discussing it now can help you figure out what your partner wants long-term from their career.

  1. Would You Rather Live In Your Dream Home In A Sub-Par Location Or Live In Your Dream Location In A Sub-Par Home?

Choosing a place to live is one of the toughest things a couple has to do. By asking this question, you get an idea of your partner’s priorities while also having fun with considering the extremes (like deciding between a mansion in a slum or a tent in Beverly Hills).

  1. Would You Rather Never Be Stuck In Traffic Again Or Never Get Another Cold?

What’s more annoying, waiting around or a stuffy nose? Finding this sort of silly stuff out can prepare you for what really bothers your partner and how you can relieve some of the stress.

  1. Would You Rather Have All Traffic Lights You Approach Be Green Or Never Have To Stand In Line Again?

Waiting is a hassle no matter where you do it, but this is a fun way to discuss what bugs your partner more.

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  1. If You Had To Be A Disney Prince Or Princess, Who Would You Choose?

Is your partner more a wily Jasmine or an adventurous Ariel? And are you more Aladdin or Prince Eric? Find out how well your fantasies pair up.

  1. If Mars Was Habitable, Would You Accept A One-Way Ticket There?

Fun because of the sci-fi Mars angle, but there’s more to this question. This is a clever way to find out just how adventurous your partner is, and how much they include you in their wildest dreams.

  1. If You Were Immortal For A Day, What Would You Do?

This question can lead to some really zany answers. If you could do anything and not die for one day, what superhuman things would you do? Jump off buildings, crash cars, or rob banks? See what crazy things your partner’s mind comes up with.

  1. If You Could Switch Lives With One Celebrity, Who Would It Be?

There’s a lot of fun to be had in searching for a celebrity with all the dream life scenarios and none of the baggage that often comes with it. Bonus points if you can hit on a celebrity couple you’d both be happy changing lives with.

  1. If You Could, Would You?

A question this open can lead to either a laugh or a serious confession. Find out which by dropping it in a conversation where your partner could connect it with any number of topics.

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Enjoying a laugh with others is great, but if you’re looking to also cover the important topics in life, you need deep conversation starters that can be funny while holding a lot of promise for long, interesting life, love, death, and everything in between.

  1. Would You Break The Law To Save A Loved One?

A head-scratcher with an amusing twist: definitely one of the best deep and funny conversation starters. Here, you can discuss not just whether laws or love are more important, but which silly or serious laws are worth breaking.

  1. Would You Rather Live Life With No Inhibitions Or Live Life With No Stress?

What plagues your conversation partner more: holding themselves back or holding onto the stress of everyday life? Get a serious answer while also having fun considering what you would do without either quality.

  1. If You Didn’t Have To Sleep, What Would You Do With The Extra Time?

Modern life is nonstop, and no one has enough free time. Find out what everyone wishes they had time to do. You might also find out who is dying to fight crime at night.

  1. You’re A Mad Scientist, What Scientific Experiment Would You Run If Money And Ethics Weren’t An Issue?

Who hasn’t wanted to be a James Bond villain at some point? Let your mind roam over the possibilities and practice your evil scientist laugh at the same time.

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  1. If You Became Famous, Would You Enjoy The Limelight Or Miss Your Privacy?

A fun chance to dream of fame while also considering the costs and benefits of achieving the dream.

  1. If You Could Be Anywhere Now, Where Would You Be?

A nice open question that invites discussions of far-off places and leaves room for nostalgia and amusing responses.

  1. If You Could Witness Any Event Past, Present, Or Future, What Would It Be?

Would you rather be with Alexander the Great as he conquers the world or takes down the Berlin Wall? Or, would you rather be with the first people to settle on a new planet? The choice will say a lot about the person you are talking to.

  1. What Questions Would You Like To Ask A Time Traveler From 200 Years In The Future?

A question is sure to bring in some very interesting—and some very funny—responses. What is the one thing you want to know about the distant future?

  1. Would You Rather Have A Horrible Job, But Be Able To Retire Comfortably In 10 Years Or Have Your Dream Job, But Have To Work Until You Were 60?

Should you love your work, or just get it over with? A great question for after-work drinks.

  1. Would You Rather Have A Golden Voice Or A Silver Tongue?

What gets you farther in life: the perfect voice or using the right words? A deep conversation starter that also gives you the chance to practice your sexiest radio voice with friends.

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  1. Would You Rather Change Your Appearance Or Your Personality?

This question offers a chance to dream of being a model or having a perfect personality while leaving room to discuss whether you can really still be you if you change either your appearance or personality too drastically.

  1. What Would You Do Without Electricity For 3 Days?

Think of the horror: no computer, no phone, no TV! But maybe you’d have a chance to do something you’ve put off for too long: build something, take a hike, or just sit around and enjoy the silence.

  1. If You Could Be A Fictional Character, Who Would It Be?

You’ll get a nice mix of serious, thoughtful answers and amusing ones with this question. A good chance to pick out the book snobs and comic book readers among your friends.

  1. When You Were A Kid, What Did You Think Being This Age Would Be Like?

Discuss all the amusing stereotypes your younger self had while also digging a little deeper into the nature of aging and how life is never quite how you expect it to be.

  1. What Single Thing Makes You Most Nostalgic?

Take a trip down nostalgia lane, but be sure to slow down and consider not just what makes you nostalgic but why. Even better, take the conversation around a philosophical turn and consider why we are nostalgic in the first place.

  1. What Would Your First Decision Be If You Were Elected President?

In this heated political time, everyone has an opinion about how their country should be run. So, what would you do first? Make serious changes to taxes, the military, or immigration? Or would you declare a national ice cream day?

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  1. Who Do You Stalk Most Often On Social Media?

Celebrities, former romantic partners, or old friends you haven’t talked to in ages: make your confession.

  1. When Was The Best Reason You Faked Being Sick?

The perfect opportunity to discuss your own Ferris Bueller moment.

  1. What Are Things That You Should Not Say At Your Own Wedding?

Giggle over the absolutely worst things to say on the most important day of your life.

  1. What Are Some Things You Shouldn’t Say At Work?

What does she really wish she could say to her boss? Something good enough to get a laugh, most likely.

  1. What’s The Weirdest Gift You Ever Received?

It’s a great chance to tell some funny stories about the odd things people give you.

  1. What Is The Worst Advice That You Got That You Actually Listened To?

Another chance to tell a great story that’s sure to have a funny ending.

  1. What’s The Worst Thing You Can Say On A First Date?

Like the wedding question above, giggle over saying all the wrong things out loud.

  1. If You Were In A Circus, What Would Your Job Be?

Would she be on the trapeze or get shot out of a cannon? A fun chance to imagine a magical kind of world.

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  1. What Is The Absolute Weirdest Nickname Someone Has Given You?

We’ve all had friends try to give nicknames that fell flat. Share yours and have a new secret name for each other.

  1. Out Of All The World’s Languages, Which One Sounds Funniest To You?

Here’s a chance to practice your Swedish Chef impression.

  1. If Hollywood Made A Movie About Your Life What Would It Be Rated And Who Would Be The Star?

Find out if she’s a hard-R sort of girl or a sweet-G and then laughs about the actors who could play her…and you.

  1. If You Could Give Your Best Friend A Tattoo In Their Sleep, What Would You Ink Them With?

She’s sure to crack up at the mischievous fun she could have given out embarrassing tattoos.

  1. If You Were Going To Rob A Bank, What Sort Of Disguise Would You Wear?

It’s a fun chance to come up with some ridiculous scenarios and even more ridiculous disguises.

  1. Would You Rather Go About Your Normal Day Naked Or Fall Asleep For A Year?

It’s a choice between the ultimate embarrassment or the loss of precious time.

  1. Would You Be Super Strong Or Change Into Animals?

You can laugh about the superpowers you always wanted, and what animals would you least want to transform into.

  1. Would You Rather Eat A Handful Of Hair Or Lick Three Public Telephones?

Always a great one if you want an easy grossed out giggle.

  1. Would You Rather Eat A Stick Of Margarine Or Drink A Small Bottle Of Tabasco Sauce?

This question has the extra edge that there’s a potential dare lurking just behind it.

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  1. Would You Rather Have A Horse’s Tail Or A Unicorn Horn?

Get your conversation partner to really picture this one, then try to work through which is easier to pull off and still look good.

  1. Would You Rather Wear Clown Makeup Or Wear A Tutu Every Day For A Year?

Another chance to imagine just how silly you could possibly look, and maybe convince someone to try the makeup or tutu on.

  1. Would You Rather Have Overly Large Hands Or Very Small Feet?

Just think how hard it would be to pick up things with massive hands, or how hard to walk with those tiny feet.

  1. Would You Rather Always Have To Sing Instead Of Speaking Or Dance Everywhere You Went?

No matter the answer, get the person to demonstrate their choice for a while.

  1. Would You Rather Wear A Bathing Suit Or Wear Formal Attire Everywhere You Go For The Next Two Weeks?

A great question that can lead to discussions of just how out of place the choice would be in some situations.

  1. Would You Rather Always Have To Enter Rooms Backwards Or Always Have To Somersault Out?

Find out, then get them to demonstrate their choice.

  1. Would You Rather Never Eat Your Favorite Food For The Rest Of Your Life, Or Only Be Able To Eat Your Favorite Food?

Silly, but with that little thoughtful edge that might make someone laugh but think twice before answering.

  1. Would You Rather Your Parents, Or Your Crush Be Able To Read Your Thoughts?

You’ll get a laugh just seeing the person wrestle with the potential embarrassments.

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  1. Would You Rather Swap Lives For A Day With Madonna Or The British Queen?

Both fun and funny, and a chance to imagine how those ladies really live.

  1. Would You Rather Be Famous And Have A Scandal Or Two, Or Never Be Talked About In The Media At All?

This is a setup for some great stories about the best and worst celebrity scandals you could have.

  1. Would You Rather Sing Karaoke On National TV Or Be Interviewed About Everything In Your Life For The Local Paper?

Pick your embarrassment: singing on the national stage or everyone you know knowing everything about you. Yikes.

  1. Would You Rather Be Able To Read The Thoughts Of Your Boss/Employees Or Whom You Date?

Whose thinking what about you, and why do you want to know so bad?

  1. Would You Rather Be Stranded In America Or Europe For The Rest Of Your Life?

Give vent to a few of your favorite stereotypes. Are you stuck with the cheese-eating French or the Big Mac attacking Americans?

  1. Would You Rather Relive High School And Get A Million Dollars, Or Spend A Year As A Clown And Get A Million Dollars?

For many of us, high school and being a clown would be equally humiliating experiences to laugh over.

  1. Would You Rather Be Left Alone With Fifteen Kids For A Day, Or Have To Spend The Day Mediating Between A Democrat And A Republican?

A tough question in these times, but come on, take the kids.

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  1. Would You Rather Have To Abstain From Alcohol Or From Caffeine For The Rest Of Your Life?

A horror choice to make for anyone who works hard in the day and plays at night.

  1. Would You Rather Snort Obnoxiously Every Time You Laughed Or Have A Voice That Sounded Exactly Like Janice From Friends?

Get your best Janice impression ready and see who gives it a snort.

  1. Would You Rather Have Unlimited Free Therapy Sessions Forever Or A One-Time Three-Hour Life Session With Oprah?

See who in the group gives you an “OMG Oprah” response.

  1. Would You Rather Have Your Life Be Narrated (Publicly) By Morgan Freeman Or Alec Baldwin?

Another great chance to do impressions, and talk about who has the coolest voice out there.

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  1. Would You Rather Spend The Rest Of Your Life Always Cold Or Always Exhausted?

This is a great one to get people to groan over after a long day of work during the winter.

  1. Would You Rather Be Super Intelligent But A Huge Asshole, Or Insanely Kind But Also Incredibly Stupid?

Stupid but kind…what’s the worst that could happen? Laugh about the potential consequences.

  1. Would You Rather Spend Four Total Hours Of Your Day Commuting To And From Work In A Super Luxurious Car, Or Spend Only One Hour Of Your Day Commuting To And From Work But On The Smelliest, Hottest, Most Crowded Bus Ride That’s Ever Existed?

The sort of question every commuter has considered, a devil’s bargain, but which side will they take?

  1. Would You Rather Have All Of Your Google Searches, Or All Of Your Text Messages, Be Broadcasted To Everyone On Facebook?

Where are people’s worst secrets hiding? Have a laugh at the shock of either idea occurring to you or others.

  1. Make Up A Song About The Host Of The Party.

You can look to “Master of the House” from Les Miserables for inspiration.

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  1. Call Someone And Confess Your Newfound Love For Justin Bieber.

Solidify this one by belting out the chorus to “Never Say Never.”

  1. Tell A Bizarre 2-Minute Story About The Night You Slept In The Woods.

Be sure to really spin the yarn and then wow them with the ending.

  1. Stand Up And Professionally Introduce Yourself To Everyone. Now Convince Them As To Why They Should Vote For You To Be The Next Spokesperson For The Elephants.

You may want to prepare a PowerPoint presentation – the elephants are worth the effort.

  1. Style Your Hair With At Least Ten Paper Clips. When You Are Finished, Post A Selfie To Social Media.

Duck lips should complete the look nicely.

  1. What Sports Would Be Funniest If The Athletes Had To Be Drunk While Playing?

Bowling, baseball, something else?

  1. What’s Your Favorite Number?

Can I get yours?? ha!

  1. What’s Your Most Favorite Way To Waste Time?

Do they love to get lost in a good book or take a long walk?

  1. What Is The Trending Activity To Do Today That Annoys You?

They can only pick one!

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  1. Do You Watch Comedy Movies After Watching A Horror One At Night?

Do they have another amazing way to go to sleep?

  1. Do You Believe In Love At First Sight?

Has it happened to them before?

  1. Do You Think Jack Could Have Really Fit On The Headboard At The End Of The Movie, Titanic?I mean, it was pretty wide…
  1. What Are Things That You Should Not Say At Your Own Wedding?

Or, at other people’s weddings?

  1. If You Had An Imaginary Friend, What Would His/Her Name Be?

Did they have one growing up?

  1. What Do You Think You Will Look Like When You Are Old?

Are they worried about that at all?

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