The Most Fascinating, Fun & Funny This or That Questions

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Asking a series of “this or that questions” may seem like just an easy way to pass the time, but it’s also a great way to learn a little more about how people see the world.

Posing the right either/or questions is a fun way to find out what people really think and feel, and it can often lead to even deeper and more interesting conversation topics.

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And the good news is that you don’t have to waste money buying the card game in order to play.

To help you get started, in this post I’ve rounded up more than 200 thought-provoking, fun and funny this or that questions that you can ask to break the ice and get to know people better.

The Ultimate List of This or That Questions

Breaking Down the Absolute Best Questions for the This or That Game

Fun & Funny This or That Questions

A group of friends laughs while sitting around talking
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What makes this or that questions funny and fun is the way they make you think about familiar topics in new and unique ways.

Each of the prompts below touches on aspects of life we all experience everyday – from food and the weather to entertainment and social media – but positions them as this or that questions that will open your mind and make you rethink some of your preferences.

Books or TV?

TV shows or movies?

Hollywood movies or indie movies?

Prestige TV or Trashy TV?

Takeout or a home cooked meal?

Pick up or delivery?

Board games or card games?

Video games or books?

Bike or car?

Roller blades or roller skates?

Car or truck?

Train or bus?

Paperback or Hardcover?

Real book or e-reader?

E-reader or tablet?

Summer or Spring?

Spring or Fall?

Fall or Winter?

Rural or urban?

Vegetarian or vegan?

Desert or arctic?

Pop or soda?

Pepperoni or sausage?

Toilet paper or bidet?

Waffles or flapjacks?

Day or Night?

Football or soccer?

Cash or card?

Wings or nachos?

Bricks and mortar or online stores?

Jacuzzi or Sauna?

Basketball or baseball?

Dress shoes or dress boots?

Cake or cupcake?

Ice cream or popsicle?

Text or call?

Call or in person?

Bacon or eggs?

Road trip or long flight?

Dogs or cats?

Horror movie or comic book movie?

Tik Tok or Instagram?

Twitter or Facebook?

Loyal friend or rich friend?

New computer or new tablet?

Save up or spend now?

Hardwood floors or carpet?

School or work?

Flats or pumps?

Cereal or toast?

Pop or rap?

Hot tea or hot coffee?

Paper or plastic?

Camping or glamping?

Kayaking or canoeing?

Hats or no hats?

Burger King or McDonald’s?

Red pill or blue pill?

Pencil or pen?

Gold or platinum?

Globetrotter or homebody?

Short hair or long hair?

Pitching or catching?

Amusement parks or carnivals?

Receiving or giving?

Pizza or pasta?

Penthouse or mansion?

Workout class or solo workout?

Hot toddy or hot chocolate?

Shakes or smoothies?

Small group hang or big party with a large group?

Right side or left side of the bed?

Perfume or eau de toilette?

Lots of free time or busy schedule?

Laptop or desktop?

Sandwich or wrap?

Teamwork or flying solo?

Cardigan or pullover?

Khakis or jeans?

Bar of soap or shower gel?

Shoes or sandals?

Loud or quiet?

Horror or comedy?

Coke or Pepsi?

Milk chocolate or dark chocolate?

Sweet or sour?

Truth questions or dare questions?

Bumper cars or ferris wheel?

Straight hair or curly hair?

Romance or friendship?

Lip chap or lip gloss?

Tattoos or piercings?

Red wine or white wine?

Liquor or beer?

Reading or watching?

Homemade or store bought?

Blueberry or raspberry?

Legal pad or notebook?

Salt water or fresh water?

Snow or rain?

French fries or onion rings?

Email or snail mail?

Theme park or amusement park?

Ice skating or roller blading?

Star Wars or Star Trek?

Taylor Swift or Katy Perry?

Orange juice or apple juice?

Chicken nuggets or chicken wings?

Real Christmas tree or fake Christmas tree?

Real nails or stick ons?

High heels or flats?

Water guns or paintball guns?

Lillies or tulips?

First date or wedding day?

Earrings or real rings?

Chicken or fish?

Real hardwood or fake hardwood?

Loveseat or couch?

Bad boys or good guys?

Gloves or mitts?

Hot or cold?

TV or radio?

Long nails or short nails?

Online news or TV news?

Gummy bears or Sour patch kids?

Peanuts or almonds?

Drip coffee or espresso?

Black coffee or with milk?

Pencil crayons or real crayons?

Batman or Superman?

DC or Marvel?

George Clooney or Brad Pitt?

Ryan Reynolds or Ryan Gosling?

Cruise ship or beach vacation?

Drapes or blinds?

Dark meat or light meat?

Galaxy phone or iPhone?

Salsa or sour cream and onion dip?

Burrito or taco?

Hot dog or burger?

Eater Bunny or Santa Claus?

Whip cream or ice cream?

Writing or dictating?

Roller coasters or bungee jumping?

Dirty This or That Questions

This or That Questions Dirty - Intimate couple holding wine glasses
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One of the best ways to spice up the questions game is to mix in a few flirty, dirty and sexual this or that questions that will take your minds (to say nothing of your other body parts) to some fun and naughty places.

Two girls and one guy or two guys and one girl?

Stripper or pornstar?

Talk dirty or act dirty?

Sex in public or sex in private?

Sexting or dirty phone call?

Sexy underwear or fully naked?

Shower sex or jacuzzi sex?

Ocean sex or pool sex?

Hot wax or ice cubes?

Give oral or get oral?

Doggy style or missionary?

Teacher’s pet or teacher?

Sexy librarian or sexy nurse?

Sexy dance or sexy massage?

Very hairy or completely bare?

Top or bottom?

Hair pulling or biting?

Orgy with ugly people or monogamous relationship with really hot asexual person?

Deep This or That Questions

Two people talk and ask deep this or that questions

It may seem like an oxymoron, but there really are some deep this or that questions that can help you get to know the person (or people) you’re playing the this or that game with on a deeper and more intimate level.

Each of the questions below touches on an interesting, challenging or intimate topic that will reveal more about the answerer’s personality, philosophy and tastes.

Rich and famous or rich and anonymous?

A few really good friends or lots of casual friends?

Short happy life or long mediocre life?

Fulfilling career and no family or great family and bad job?

Infamy or anonymity?

Expertise in one subject or base-level knowledge in every subject?

Great physical strength or great mental strength?

Great wealth or great intelligence?

Bad job with good colleagues or good job with no colleagues?

Unremarkable but good life, or one-of-a-kind life with lots of ups and downs?

Photographic memory or terrible memory but high intelligence?

One best friend, or a lot of casual acquaintances?

Work from home or work in an office?

Live in a cabin in the woods or live in a condo downtown?

Power or respect?

Live your whole life in isolation or whole life in public?

Have a book written about you or have a movie written about you?

Live alone your whole life or have a roommate your whole life?

Democracy or benevolent dictatorship?

Live in your own country and never travel, or only live abroad where you can’t speak the language?

Be ignored completely or be teased relentlessly?

Lots of affection but no romance or lots of lust but no affection?

End sexism or end racism?

Live forever and watch friends and family die or live normal length and die before them?

Sometimes fail but learn a lesson, or always succeed but never learn humility?

This or That Questions for Teens

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The best this or that questions for teens are the ones that touch on subjects that teenagers already have in mind – like school, their friends and pop culture – but put a unique spin on them that makes them think about familiar subjects in new and original ways.

College or University?

Part-time job or full-time job?

Mom or dad?

Introvert or extrovert?

Jock or nerd?

Boys or girls?

Party or mall?

Own car or own apartment?

Homework or detention?

Freaks or geeks?

New clothes or new jewellery?

New phone or new laptop?

Piercings or tattoos?

Frenemies or rivals?

Use a flip phone forever or use a desktop forever?

Never go to a party again or never use social media again?

Spend time alone without your phone or have your phone but be too busy to use it?

Texting or video calls?

Netflix or Disney+?

No more sugar or no more carbs?

Justin Bieber or Shawn Mendes?

Ariana Grande or Dua Lipa?

Harry Potter or Bilbo Baggins?

Be a contestant on the Bachelor/Bachelorette or a contestant on Who Wants to Be a Millionaire?

Be a famous athlete or a famous musician?

Win an Oscar for an indie movie no one saw, or be in a blockbuster movie that gets bad reviews?

What’s better: only child or lots of siblings?

Be famous or have a famous member of your family?

10 pets or no pets?

Bad breath or bad body odor?

This or That Questions for Kids

Whereas a lot of the questions above are designed to get you thinking outside the box and approaching topics in new and unique ways, the main benefit of this or that questions for kids is to have some fun.

The below questions will keep kids engaged and all touch on subjects that most kids will already be familiar with.

Peanut butter or jelly?

Burt or Ernie?

Kermit the Frog or Big Bird?

Frozen or Moana?

Up or down?

Toys or candy?

High fives or hugs?

Friends or family?

Cartoons or live action?

Video games or board games?

Outdoors or indoors?

Sports or arts?

Crafts or karate?

Pick your nose or pick your friends?

Toots or burps?

Frisbee or hula hoop?

Hop scotch or jump rope?

Sesame Street or Paw Patrol?

Cookies or cake?

More Great Stuff From Irreverent Gent:
More This or That Questions From Around the Web:

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About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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