Science of People - Logo

500 Best This or That Questions For Great Conversations

People who ask more questions1 in conversation tend to get rated as more likable. You can use this to your advantage by asking this or that questions! 

This article contains a complete list of 500 this or that questions for every category you could think of. These questions are your gateway into entertaining and insightful conversations with friends, dates, and family members. 

What are This or That Questions?

In a this or that question, each person has to choose one of two choices. 

They are a fun way to lighten up any conversation and help to break the ice. You can use them at team meetings or as conversation starters. They can be surprisingly revealing!

Whether you ask these in rapid-fire succession or pause to discuss why the person chose what they did, you can look forward to some laughs and surprises along the way.

25 Best This or That Questions

  1. Notorious or unnoticed? 
  2. Play it safe or risk it all?
  3. Misunderstood or unappreciated? 
  4. Loved or respected? 
  5. Heartbreaker or heartbroken? 
  6. Specialist or generalist?
  7. Past or future? 
  8. Dine alone or watch a movie alone? 
  9. Whisper or shout? 
  10. Slytherine or Gryffindor?
  11. Read thoughts or speak to animals? 
  12. No more social media or no more messaging apps?
  13. Cookies or cake? 
  14. Be an only child or the oldest of 12? 
  15. Tomato is a fruit, or tomato is a vegetable? 
  16. Warm climate or all seasons? 
  17. Happy songs or sad songs? 
  18. Windows open or closed? 
  19. Government aid or community support? 
  20. Reality TV shows or scripted dramas?
  21. Scented candles or natural fresh air?
  22. A day at the beach or a day at the amusement park?
  23. Classic literature or modern bestsellers?
  24. Learning a new language or learning a musical instrument?
  25. Watching sunrise or stargazing?

This or that questions are a great conversation tool. However, if you want to learn more conversation tools and skills and elevate your conversation game to the next level, you might enjoy this goodie:

Communicate With Confidence

Do you struggle with small talk? Do you often run out of things to say or feel awkward and self-conscious in social situations?

💪 Speak so people listen,
🤐 No more awkward silences,
🚫 No more small talk.

This or That Questions for Couples

  1. Hugging or kissing? 
  2. Calling or texting?
  3. Talking or cuddling? 
  4. Affirmation or gifts? 
  5. Quality time or acts of service?
  6. Plan it or wing it? 
  7. Date night out or in? 
  8. Travel with friends or just us? 
  9. Logic or emotions? 
  10. PDA or no PDA? 
  11. Meet the parents or meet the ex? 
  12. Fancy dinner or takeout and a movie? 
  13. Growth or security? 
  14. Comedies or horror films?
  15. Marriage or career? 
  16. Dinner at a fancy restaurant or homemade dinner by candlelight?
  17. Morning cuddles or goodnight kisses?
  18. Sharing dessert or getting separate treats?
  19. Fitness duo or lazy Sundays together?
  20. Planning the future or living spontaneously?
  21. Couple’s costumes or going as individuals?
  22. Night in with board games or night out dancing?
  23. Shared hobbies or separate interests?
  24. Joint bank account or separate finances?
  25. History museum or haunted house?

Pro Tip: Go beyond this or that and find hundreds of dynamic questions to ask your girlfriend or boyfriend!

Emotionally Deep This or That Questions

  1. Fulfillment or security?
  2. Compassion or justice?
  3. Self-respect or love?
  4. Authenticity or success?
  5. Wisdom or intelligence?
  6. Inner peace or worldly influence?
  7. Forgiveness or vindication?
  8. Freedom or stability?
  9. Passion or rationality?
  10. Individuality or belonging?
  11. Acceptance or improvement?
  12. Creativity or knowledge?
  13. Intimacy or independence?
  14. Living in the moment or planning for the future?
  15. Resilience or sensitivity?
  16. Acknowledgement or anonymity?
  17. Altruism or reciprocity?
  18. Self-discovery or community service?
  19. Transparency or mystery?
  20. Inspiration or comfort?
  21. Courage or patience?
  22. Legacy or pleasure?
  23. Adventure or contentment?
  24. Innovation or tradition?
  25. Spirituality or science?

Funny This or That Questions

  1. Ninjas or Pirates?
  2. Unicorn with a mustache or a monkey in a top hat?
  3. Time travel to the past in a spacesuit or to the future in a dinosaur costume?
  4. Fight one horse-sized duck or a hundred duck-sized horses?
  5. Have fingers for toes or toes for fingers?
  6. Be a reverse centaur or a reverse mermaid/merman?
  7. Sneeze confetti, or does your laugh sound like a frog?
  8. Only be able to whisper everything or shout everything?
  9. Have a pet dragon or be a dragon?
  10. Be able to speak all foreign languages or be able to speak to all animals?
  11. Have spaghetti for hair or sweat maple syrup?
  12. Fight with a lightsaber or cast spells with a wand?
  13. Ride a giant snail to work every day or a regular-sized giraffe?
  14. Live in a world where everything is a musical, or everyone talks in rhyme?
  15. Always have to enter rooms by announcing your name or always have to exit by doing a backflip?
  16. Wear clown shoes every day or a clown wig?
  17. Use a banana as a phone or a shoe as a hat?
  18. Have a permanently clogged nose or a piece of popcorn stuck between your teeth forever?
  19. Have the ability to teleport but only to places you’ve never heard of or fly but only two feet off the ground?
  20. Have legs as long as your fingers or fingers as long as your legs?
  21. Live without music or live without television?
  22. Have every movie you watch slowly turn into “Shrek” halfway through or every song you listen to slowly turn into “All Star” by Smash Mouth?
  23. Wear a tuxedo made of taxidermy or a swimsuit made of live fish?
  24. Have hiccups for the rest of your life or always feel like you need to sneeze but can’t?
  25. Have a head the size of a tennis ball or the size of a watermelon?

This or That Food Questions

  1. Sweet or savory?
  2. Coffee or tea?
  3. Breakfast or dinner?
  4. Chocolate or vanilla?
  5. Ice cream or frozen yogurt?
  6. Pizza or pasta?
  7. Burger or tacos or sandwiches?
  8. Cake or donuts?
  9. Hot coffee or iced coffee?
  10. Ketchup or mustard?
  11. Steak or seafood?
  12. Salad or soup?
  13. Smoothies or milkshakes?
  14. Cheese platter or charcuterie board?
  15. Baking or grilling?
  16. Home-cooked meal or takeout?
  17. French fries or baked potatoes?
  18. Pepsi or Coke?
  19. White chocolate or dark chocolate?
  20. Broccoli or chicken nuggets?
  21. Hot dogs or hamburgers?
  22. Asian cuisine or Mexican cuisine?
  23. Chips or popcorn?
  24. Food truck or restaurant?
  25. Waffles or pancakes?

This or That Questions for Work

  1. Remote work or in-office?
  2. Early bird schedule or night owl shifts?
  3. Team collaboration or solo projects?
  4. Structured routine or flexible scheduling?
  5. High-stress, high-reward, or steady, low-pressure work?
  6. Team outing or virtual meeting? 
  7. Snack stash or drink station? 
  8. An angry boss or an angry client? 
  9. Education or experience?
  10. Free lunch or on-site gym?
  11. Emails or meetings?
  12. Which is worse—Sunday night or Monday morning? 
  13. Office romance or office drama?
  14. Work for a company or be your boss? 
  15. Start early and finish early, or start late and finish late? 
  16. 4-day work week or 5-day work week? 
  17. Type or write notes? 
  18. One-on-one meeting or group meeting? 
  19. Foosball or ping pong in the break room? 
  20. Travel for work or business dinners?
  21. Desk job or service job?
  22. Salary raise or additional benefits? 
  23. Funding or bootstrapping?
  24. Which question is worse, “Tell me about you?” or “What is one of your weaknesses?”
  25. Christmas bonus or extra PTO?

This or That Questions for Kids

  1. T-Rex or Stegosaurus? 
  2. Christmas every day or summer year round? 
  3. Squishy toys or toy cars? 
  4. Play outside or inside?
  5. Forts or climbing trees? 
  6. Tadpoles or toads?
  7. Lions or tigers?
  8. Talking or reading?
  9. Drums or guitar? 
  10. Art class or math class? 
  11. Halloween or Christmas?
  12. Oreos with milk or without milk? 
  13. Superheroes or magic?
  14. Puppies or dolphins?
  15. A giant grasshopper or a tiny dinosaur? 
  16. Swim in jello or swim in chocolate milk? 
  17. Have a pet rhinoceros or porcupine? 
  18. Ride on a kangaroo or an eagle? 
  19. Live in a submarine or on a tiny island? 
  20. Hide and seek or tag?
  21. Pencil or crayons?
  22. Lost in the woods or lost in the mountains? 
  23. Parachuting or bungee jumping? 
  24. Fries with peanut butter or pizza with icing? 
  25. Baseball or basketball or soccer?

This or That Questions for Gen Z

  1. TikTok or Instagram stories?
  2. Snapchat streaks or Instagram DMs?
  3. eSports or traditional sports?
  4. Streaming services or cable TV?
  5. Online multiplayer or single-player video games?
  6. Podcasts or vlogs?
  7. Electric scooters or bikes?
  8. Memes or viral challenges?
  9. Online learning or classroom learning?
  10. Fast fashion or sustainable brands?
  11. Plant-based diet or traditional diet?
  12. Thrift shopping or online shopping?
  13. Group chats or DMs?
  14. Digital art or traditional art?
  15. Pop music or rock music?
  16. Cryptocurrency or traditional currency?
  17. Indie music or mainstream pop?
  18. Texting or voice messages?
  19. Reality TV or YouTube dramas?
  20. Influencers or celebrities?
  21. Wireless earbuds or over-the-ear headphones?
  22. Climate action or social justice?
  23. Augmented reality games or console games?
  24. Dark mode or light mode?
  25. Mental health apps or fitness apps?

This or That Questions for Millenials

  1. Facebook or Instagram?
  2. Snapchat or TikTok?
  3. Harry Potter or The Hunger Games?
  4. Netflix or YouTube?
  5. Smartphone or tablet?
  6. Emojis or GIFs?
  7. Spotify or Apple Music?
  8. Uber or Lyft?
  9. Airbnb or traditional hotel?
  10. Online shopping or in-store shopping?
  11. PlayStation or Xbox?
  12. Superman or Batman?
  13. Avocado toast or artisanal coffee?
  14. Podcasts or audiobooks?
  15. The Office or Parks and Recreation?
  16. Bitcoin or stocks?
  17. Craft beer or fancy cocktails?
  18. Fitness tracker or smartwatch?
  19. Game of Thrones or Breaking Bad?
  20. E-books or physical books?
  21. Hashtags or memes?
  22. Virtual reality or augmented reality?
  23. Home cooking or food delivery apps?
  24. Marvel or DC?
  25. Yoga or CrossFit?

This or That Questions for Gen X

  1. MTV or VH1?
  2. Nintendo or Sega?
  3. Grunge or hip hop?
  4. Walkman or Discman?
  5. The Breakfast Club or Ferris Bueller’s Day Off?
  6. AOL or MSN?
  7. Friends or Seinfeld?
  8. Mixtape or compilation CD?
  9. VHS or Betamax?
  10. Blockbuster or local video store?
  11. G.I. Joe or Transformers?
  12. Skateboarding or BMX?
  13. Dial-up internet or public library computers?
  14. Atari or arcade?
  15. Saved by the Bell or Beverly Hills, 90210?
  16. Tamagotchi or Furby?
  17. The X-Files or Buffy the Vampire Slayer?
  18. Slap bracelets or mood rings?
  19. Trapper keeper or Five Star notebook?
  20. Teenage Mutant Ninja Turtles or Power Rangers?
  21. Reality Bites or Singles?
  22. LaserDisc or DVD?
  23. Garbage Pail Kids or Cabbage Patch Kids?
  24. Hypercolor shirts or acid-wash jeans?
  25. Fresh Prince or In Living Color?

This or That Questions for Boomers

  1. Beatles or Rolling Stones?
  2. Woodstock or Monterey Pop?
  3. Vinyl records or 8-track tapes?
  4. Bell bottoms or mini skirts?
  5. Volkswagen Beetle or Ford Mustang?
  6. Typewriter or pen and paper?
  7. Rotary phone or payphone?
  8. I Love Lucy or The Andy Griffith Show?
  9. Elvis Presley or Johnny Cash?
  10. Drive-in movie or movie theater?
  11. Fondue or Jell-O mold?
  12. Bob Dylan or Simon & Garfunkel?
  13. Physical map or ask for directions?
  14. Polaroid camera or 35mm film camera?
  15. Hippies or disco?
  16. Cassette tape or radio?
  17. Pong or pinball?
  18. Lava lamp or disco ball?
  19. Led Zeppelin or Pink Floyd?
  20. Star Trek original series or MAS*H?
  21. Encyclopedia set or library card?
  22. Station wagon or minivan?
  23. The Godfather or Jaws?
  24. Manual typewriter or electric typewriter?
  25. Saturday morning cartoons or after-school specials?

This or That Questions for College Students

  1. Study abroad or local internship? 
  2. Graduate early or finish with your friends?
  3. Have your browsing history public, or has the professor read your texts? 
  4. Essay questions or multiple choice? 
  5. Dorm food or cafeteria food? 
  6. Themed party or coffee with your best friend? 
  7. Private or public university? 
  8. Mac or PC? 
  9. Summer classes or summer jobs? 
  10. Study in the library or dorm? 
  11. Small or large classes?
  12. Presentation or group project? 
  13. Home for the holidays or vacation with friends? 
  14. Backpack or messenger bag? 
  15. Movie night or game night?
  16. Energy drinks or coffee? 
  17. Free food or free clothes? 
  18. Get a degree you love or a degree for money? 
  19. Library or dining hall? 
  20. Party or study? 
  21. Quantum physics or philosophy?
  22. Out-of-state or in-state? 
  23. Messy roommate or loud roommate? 
  24. Easy A or challenging classes? 
  25. Electives: fun or practical?

Travel and Adventure This or That Questions

  1. Backpacking or luxury resorts?
  2. Local cuisine or familiar foods?
  3. Cityscape or countryside?
  4. Adventure sports or historical tours?
  5. Camping or glamping?
  6. Road trip or flight?
  7. Solo expedition or travel group?
  8. Cruise ship or private yacht?
  9. Hostel or five-star hotel?
  10. Travel by train or by bus?
  11. Hiking or surfing?
  12. Safari or scuba diving?
  13. Guided tours or exploring on your own?
  14. Zoo or aquarium?
  15. Winter wonderland or summer paradise?
  16. Frequent short trips or long extended vacations?
  17. Travel photography or journaling?
  18. Famous landmarks or hidden gems?
  19. Tropical island or bustling city?
  20. Sunrise hikes or sunset watching?
  21. Cultural immersion or leisurely getaway?
  22. Travel vlogging or travel blogging?
  23. Ocean stroll or country bike ride?
  24. Full itinerary or spontaneous adventure?
  25. Eco-tourism or urban tourism?

Tech and Gadgets This or That Questions

  1. Wired headphones or Bluetooth earbuds?
  2. Smartwatch or traditional watch?
  3. Console gaming or PC gaming?
  4. E-reader or tablet?
  5. iPhone or Android smartphone?
  6. Mac or PC?
  7. Online shopping or shopping in-store with an app?
  8. Digital art or hand-drawn?
  9. Streaming services or cable TV?
  10. Smart home devices or manual operation?
  11. Laptop or desktop computer?
  12. DSLR camera or smartphone camera?
  13. Fitness tracker or mobile fitness app?
  14. Video calls or voice calls?
  15. Electric car or hybrid vehicle?
  16. GPS navigation or old-school maps?
  17. Virtual assistants or personal planners?
  18. Drone photography or traditional photography?
  19. Coding software or web design tools?
  20. Subscription-based software or a one-time purchase?
  21. Noise-canceling technology or natural ambient sounds?
  22. Online multiplayer or local co-op gaming?
  23. Cloud storage or physical hard drives?
  24. Smart pens or touch-screen styluses?
  25. Online forums or social media groups?

Social Media and Communication This or That Questions

  1. Instagram posts or Snapchat stories?
  2. WhatsApp chats or Telegram groups?
  3. Facebook groups or Reddit forums?
  4. Twitter newsfeed or LinkedIn updates?
  5. Zoom video calls or Google Meet?
  6. Discord server or Slack channel?
  7. Pinterest boards or Tumblr blogs?
  8. YouTube videos or TikTok clips?
  9. Facebook messenger or text?
  10. Instagram Reels or YouTube Shorts?
  11. Blogging on Medium or WordPress?
  12. Snapchat filters or Instagram filters?
  13. Twitch streams or YouTube live streams?
  14. Spotify Podcasts or Apple Podcasts?
  15. LinkedIn networking or in-person networking events?
  16. Facebook Marketplace or Craigslist?
  17. Texts or voice memos?
  18. Instagram or Twitter?
  19. DMs or comments?
  20. Facebook or LinkedIn?
  21. Hashtags or no hashtags?
  22. Livestreams or pre-recorded?
  23. Social media detoxes or constant connectivity?
  24. Influencer culture or personal posting?
  25. Following celebrities or real-life friends?

Daily Lifestyle This or That Questions

  1. Morning routine or night routine?
  2. Home-cooked meals or takeout?
  3. Gym or home workout?
  4. Public transportation or driving?
  5. Physical books or audiobooks?
  6. Early riser or night owl?
  7. City life or rural living?
  8. Coffee shops or homebrew?
  9. To-do lists or spontaneous living?
  10. Budgeting apps or personal finance spreadsheets?
  11. Meal prepping or cooking daily?
  12. DIY or professional services?
  13. Traditional TV or smart TV streaming?
  14. Local libraries or bookstores?
  15. Daily planner or digital calendar?
  16. Cleaning day or clean as you go?
  17. Paper or digital notes?
  18. Minimalism or having collections?
  19. Indoor plants or low-maintenance decor?
  20. Energy drinks or natural boosters?
  21. Weekly grocery shopping or as-needed runs?
  22. Home office or co-working space?
  23. Scheduled relaxation or finding downtime?
  24. Fresh air breaks or power through work?
  25. Organized space or organized chaos?

Personal Growth This or That Questions

  1. Journaling or meditation?
  2. Goal setting or going with the flow?
  3. Self-help books or personal mentorship?
  4. Morning affirmations or evening reflections?
  5. Professional development or personal hobbies?
  6. Networking events or skill-building workshops?
  7. Therapy or self-reflection?
  8. Life coaching or self-guidance?
  9. Daily challenges or long-term projects?
  10. Online courses or in-person classes?
  11. Vision boards or written goals?
  12. Positive reinforcement or constructive criticism?
  13. Solo travel for growth or group retreats?
  14. Physical fitness or mental exercises?
  15. Mindfulness practices or active problem-solving?
  16. Learning a new language or mastering a skill?
  17. Saving for the future or investing in experiences?
  18. Traditional learning or alternative education methods?
  19. Reading fiction for empathy or non-fiction for knowledge?
  20. Active listening or speaking out?
  21. Time management seminars or productivity apps?
  22. Public speaking or writing skills?
  23. Work-life balance or work-life integration?
  24. Delegating tasks or mastering multitasking?
  25. Clean eating or indulging mindfully?

Relationships and Social Life This or That Questions

  1. Double dates or group gatherings?
  2. Long phone calls or face-to-face conversations?
  3. Social media connections or in-person friendships?
  4. Blind dates or dating apps?
  5. Big parties or intimate get-togethers?
  6. Making new friends or deepening existing relationships?
  7. Quick texts or handwritten letters?
  8. Large family reunions or immediate family dinners?
  9. Game nights or movie nights?
  10. Work friendships or separate social circles?
  11. Outdoor BBQs or cozy indoor meals?
  12. Concerts with friends or solo art exhibits?
  13. Friendship bracelets or matching tattoos?
  14. Long-term relationships or casual dating?
  15. Friendship goals or individual achievements?
  16. Collaborative projects or solo ventures?
  17. Online gaming friends or local sports teams?
  18. Surprise parties or planned outings?
  19. Social clubs or online forums?
  20. Heartfelt gifts or experience gifts?
  21. Reconnecting with old friends or meeting new people?
  22. Couples’ retreats or singles’ adventures?
  23. Community service or personal time?
  24. Mentoring relationships or peer-to-peer support?
  25. Open relationships or traditional monogamy?

Fashion and Style This or That Questions

  1. Jeans or chinos?
  2. Sneakers or boots?
  3. Vintage or contemporary?
  4. Dresses or suits?
  5. Handmade jewelry or designer brands?
  6. Bright colors or neutral tones?
  7. Leather or denim?
  8. Fashion magazines or fashion influencers?
  9. Caps or fedoras?
  10. Custom tailoring or off-the-rack?
  11. Streetwear or runway?
  12. Short hair or long hair?
  13. Thrift shopping or brand new?
  14. Local boutiques or international chains?
  15. Minimalist or maximalist?
  16. Wardrobe staples or statement pieces?
  17. Natural fabrics or synthetic materials?
  18. High fashion or everyday comfort?
  19. Sunglasses or hats?
  20. Watches or bracelets?
  21. Heels or flats?
  22. Graphic tees or plain shirts?
  23. Crossbody bags or backpacks?
  24. Seasonal trends or classic looks?
  25. Piercings or tattoos?

Holiday This or That Questions

  1. Elf or Die Hard?
  2. Chanukah, Christmas, or Kwanzaa? 
  3. Give presents or receive presents?
  4. School pageant or The Nutcracker?
  5. Eggnog or Cider?
  6. Skating in NYC or poolside in Florida?
  7. Open presents on Christmas Eve or Christmas morning?
  8. Sweet potato casserole or latkes?
  9. Pumpkin pie with whipped cream or apple pie with vanilla ice cream?
  10. Ugly sweater or ornament earrings?
  11. Office party or family party? 
  12. Snowball fight or build a snowman?
  13. Charlie Brown Christmas tree or blue spruce?
  14. ‘Twas the Night Before Christmas or A Christmas Carol? 
  15. Jingle Bells or Jingle Bell Rock? 
  16. Christmas caroling or Christmas market? 
  17. Make decorations or buy them?
  18. White lights or multicolored lights on the tree? 
  19. Cajun catfish or groundnut stew? 
  20. Ski lodge or lake house?
  21. Mariah Carey or Michael Bublé?
  22. Spicy hot chocolate or peppermint hot chocolate?
  23. Cut down a tree or buy a living tree? 
  24. Sugar cookies or Kwaanza cake?
  25. Advent candles, kinara, or menorah? 

This or That FAQs

What are this or that questions?

This or that questions are icebreakers where a person must choose between 2 options. The questions can be funny or silly but have the potential to reveal deeper emotions and perspectives. Some of this or that questions are intentionally vague. Part of the fun is seeing how the other person interprets the question. 

How do you ask this or that questions?

The best way to ask this or that question is to set a time limit of 5 seconds for the answer. If you play this in a group, circle so everyone answers the question rapidly. If you’re playing this game one-on-one, you can use some of these as a conversation starter. 

What are the rules for asking this or that question?

The rules of asking this or that questions are simple; you must have at least two people to play with and give each person 5 seconds to answer. You can make teams and guess what the other person will choose. Collect a point each time you guess correctly. 

What are good this or that questions?

Good this or that questions are those that spark conversation, reflect a person’s preferences, and can be thought-provoking or fun, like “Coffee or tea?” or “Travel the world or have a dream home?”

More Great Questions!

Hopefully, you have enough this or that questions to last you a while! 

But if you want to branch out and keep the fun going in other ways, consider The 30 Best Games to Play With Every Kind of Friend or even these 320 Would You Rather questions. 

How to Deal with Difficult People at Work

Do you have a difficult boss? Colleague? Client? Learn how to transform your difficult relationship.
I’ll show you my science-based approach to building a strong, productive relationship with even the most difficult people.

Please enable JavaScript in your browser to complete this form.

Get our latest insights and advice delivered to your inbox.

It’s a privilege to be in your inbox. We promise only to send the good stuff.

Please enable JavaScript in your browser to complete this form.