346 This or That Questions to Ask Your Friends

As adults, it’s easy to get wrapped up in the daily grind and forget the art of genuine connection. But that doesn’t mean the days of sleepovers, philosophical debates, and late-night texts are behind us.

Whether you’re sipping craft beer with your buddies or just texting your BFF after a long workday, these questions are your ticket to not just passing the time, but diving deep. Curious about your friend’s latest crush or partner? Got a hunch that there’s a hilarious or thought-provoking story lurking beneath that rugged exterior? A few “This or That” questions can be the catalysts to unlock those tales.

So, it’s time to turn off autopilot. Whether it’s on a night in, a weekend trip, or just a casual chat, allow yourself to get back to the basics and truly get to know the people in your circle.

This or That questions to ask…

  1. To get to know your friends
  2. To go deep
  3. About yourself
  4. Your best friend
  5. Over text
  6. On a sleepover
  7. Philosophical
  8. To get to know your friend’s crush or partner
  9. Funny

This or That questions to get to know your friends better

We’ve all been there: you’re hanging out with friends, and even though you’ve known each other for years, there’s always more to learn. Whether you’re trying to deepen those bonds with longtime friends or simply break the ice with some new acquaintance, This or That questions can be your secret weapon. They are simple, yet effective – offering insights into preferences, habits, and personality.

1. Beach vacation or mountain retreat?

2. Coffee or tea?

3. Dogs or cats?

4. Breakfast or dinner?

5. Sunrise or sunset?

6. Sweet or salty snacks?

7. Book or movie?

8. Introvert or extrovert?

9. Hiking or swimming?

10. Forever live in a small town or big city?

11. Physical books or ebooks?

12. Plants or flowers?

13. Fancy restaurant or street food?

14. Past or future?

15. Driving or being driven?

16. Art museum or history museum?

17. Skiing or snowboarding?

18. Rainy day or sunny day?

19. Football or basketball?

20. Leather or denim?

21. Classical music or rock?

22. Train journey or road trip?

23. Fitness club or outdoor workout?

24. Indoor or outdoor concerts?

25. Action movies or romantic comedies?

26. Formal attire or casual wear?

27. Money or fame?

28. Reality TV or documentaries?

29. Cooking or ordering takeout?

30. Dine in or carry out?

31. Skirts or pants?

32. Texting or calling?

33. Roller coaster or Ferris wheel?

34. Theater or cinema?

35. Horror movie or mystery novel?

36. Make a new law or get rid of one?

37. Working alone or in a team?

38. Writing or typing?

39. Couch or recliner?

40. Fiction or non-fiction?

As the conversation goes on, you also might like to ask other types of questions to get to know people in general.

Deep This or That Questions

Sure, the fun and goofy questions can be great, but sometimes you need to dig a little deeper. These This or That questions are all about creating meaningful dialogue and prompting some serious introspection. Use these prompts when you really want to understand what makes your friends tick. Just remember, these queries might stir up some strong emotions, so keep an open mind and respectful approach.

1. Live for a thousand years or live ten 100-year lives?

2. Money or job satisfaction?

3. Safety or freedom?

4. Live in a world without problems or be the person who solves them?

5. Be remembered or be influential during your lifetime?

6. Spend life alone with unlimited wealth or surrounded by people with average wealth?

7. Have the ability to change the past or see the future?

8. Achieve world peace or end world hunger?

9. Experience everything or nothing at all?

10. Have endless money or endless love?

11. Be universally liked or have unlimited power?

12. Have a constantly changing environment or a completely predictable one?

13. Love or be loved?

14. Be the funniest person in the room or the smartest one?

15. Inner beauty or outer beauty?

16. Be remembered for doing something good or be forgotten doing something great?

17. Follow your heart or your head?

18. Be respected by your peers or your children?

19. Live in the public eye or live away from civilization?

20. Timeless wisdom or youthful vitality?

21. Be feared or loved?

22. Be the richest person in the world or the healthiest?

23. Have your life be a constant loop of your happiest day or never live the same day twice?

24. Achieve your biggest dream or resolve your biggest regret?

25. Be able to hear every conversation or take back anything you say?

26. Live a life of happiness but not achieve much or achieve a lot but live a life of struggle?

27. Be poor and work at a job you love, or be rich and work at a job you hate?

28. Live in the moment or live for the future?

29. Be immortal without being able to die or live again after you die?

30. Win $50,000 or let your best friend win $500,000?

31. Be stuck in the past or never remember the past?

32. Have a high-profile job with no family for life or an average job with a family to come home to?

33. Perfect career or perfect relationship?

34. Infinite wealth or immortality?

35. Have all your dreams come true but have a 10% chance of instant death, or be just as you are now?

36. Live without music or without color?

37. Know how you will die or when you will die?

38. Give up social media or eat the same dinner for a year?

39. Live without love or live without laughter?

40. Die before your time but be remembered forever or live a long life but be forgotten immediately after death?

41. Face your biggest fear or forget your most cherished memory?

You can keep digging with our curated list of deep questions to ask friends.

This or That questions about yourself

It can be fascinating to learn how your friends perceive you and how they might answer This or That questions about your habits, preferences, or quirks. Not only is it an interesting way to gain insights about yourself, but it also provides a fun change of pace in the conversation. But remember to not take things too seriously – it’s all in the name of fun and deepening your friendships.

1. Do you think I’m more of a city person or a country person?

2. Would you say I’m more of an introvert or an extrovert?

3. Do you think I’m more of a hard worker or a smart worker?

4. Am I a dog person or a cat person?

5. Would you say I’m more of a fast food person or a homemade food person?

6. Do I seem like more of a leader or a follower?

7. Would you say I’m more optimistic or pessimistic?

8. Do you think I’m more patient or impulsive?

9. Do I seem like more of a planner or a spontaneous person?

10. Would you say I’m more artistic or analytical?

11. Do you think I prefer sweet or salty snacks?

12. Am I a winter person or a summer person?

13. Do you think I’m more into sports or arts?

14. Would you say I prefer dressing up or dressing down?

15. Am I more of a dreamer or a realist?

16. Do you think I’d prefer camping or a luxury hotel?

17. Would you say I’m a listener or a talker?

18. Do you think I’d prefer a road trip or a plane trip?

19. Would you say I’m more of a spender or a saver?

20. Do you think I prefer fancy restaurants or street food?

21. Would you say I’m more of a drama lover or a comedy lover?

22. Do I seem like more of a phone call person or a text message person?

23. Would you say I’m more romantic or practical?

24. Do you think I’m more outgoing or reserved?

25. Would you say I’m more of a homebody or an adventurer?

26. Do you think I’d prefer a beach holiday or a mountain escape?

27. Would you say I’m more of a present giver or a present receiver?

28. Do I seem like more of a rule follower or a rule breaker?

29. Do I seem like more of a people person or a solitary person?

30. Do you think I’m more of a history buff or a tech geek?

31. Do you think I prefer to plan everything out or go with the flow?

32. Do you think I prefer individual sports or team sports?

33. Would you say I’m more of a trend follower or a trendsetter?

34. Do you think I’d prefer a rainy day at home or a sunny day outdoors?

35. Would you say I’m more of a minimalist or a maximalist?

36. Do you think I’m more into reality TV or documentaries?

37. Would you say I’m more of a tidy person or a messy person?

38. Would you say I’m more of a flower person or a plant person?

You’ll find more ideas in this list of questions to ask your friends or a BFF about yourself.

This or That questions to ask your best friend

Even though you might feel like you know everything about your best friend, there’s always more to uncover. These This or That questions are designed to dig a bit deeper and reveal more about your BFF’s preferences, dreams, and quirks. Plus, they’re a fun way to pass the time on your next hangout.

1. Skiing or snowboarding?

2. Camping or hotel stay?

3. Comedy club or dance club?

4. Spend the rest of your life with a sailboat as your home or an RV as your home?

5. Big party or small gathering?

6. Stay where you are or live in another country?

7. Work hard or play hard?

8. Money or free time?

9. Fruits or vegetables?

10. Car or bike?

11. Tattoos or piercings?

12. Adventure or relaxation?

13. Swimming or sunbathing?

14. Pancakes or waffles?

15. Card game or board game?

16. Skydiving or bungee jumping?

17. Instagram or Twitter?

18. Love or career?

19. Bagel or toast?

20. Glasses or contacts?

21. Ice cream or frozen yogurt?

22. Boots or sandals?

23. Solo travel or group travel?

24. Classical music or jazz?

25. Drama or comedy?

26. Painting or drawing?

27. Rain or snow?

28. Hiking or biking?

29. Laptop or desktop?

30. Meat or veggies?

This or That questions to ask your friends over text

Texting is a fantastic way to keep the dialogue rolling, especially when distance or busy schedules make it tough to meet up. It’s time to spice up your group chats or direct messages with some entertaining This or That questions. These prompts are designed to be quick and engaging, ideal for a lively texting exchange. So, let’s dive into some intriguing queries that you can just copy, paste, and send!

1. Action movies or romantic comedies?

2. Chocolate or vanilla?

3. Paris or Tokyo?

4. Books or movies?

5. Sauna or steam room?

6. Tropical island or ski resort?

7. Travel or stay home?

8. Harry Potter or Lord of the Rings?

9. New clothes or new phone?

10. Solo or group travel?

11. Morning or night?

12. City life or country life?

13. Star Wars or Star Trek?

14. Hot or cold weather?

15. Classic art or modern art?

16. Flying or driving?

17. Gym or home workout?

18. Pizza or pasta?

19. Cardio or weights?

20. Facebook or Instagram?

21. Sneakers or sandals?

22. Bath or shower?

23. Wine or beer?

24. Gold or silver?

25. Big party or small gathering?

26. Snowy Christmas or sunny Christmas?

27. Pancakes or waffles?

28. Dining out or delivery?

29. Roller coaster or merry-go-round?

You might also like some additional tips to keep the conversation going over text.

This or That Questions to ask on a sleepover

Sleepovers aren’t just for kids; they can be a ton of fun for adults too! But let’s be real, after a certain point, you need something more than just another movie to keep the fun going. That’s where these This or That questions come in handy. These prompts are perfect for sleepovers, offering a mix of lighthearted, personal, and downright hilarious options.

1. Late-night movie or late-night chat?

2. Indoor camping or outdoor camping?

3. Play board games or watch a movie?

4. Flashlight tag or shadow puppets?

5. DIY photoshoot or makeover session?

6. Watch the stars or watch a meteor shower?

7. Fairy lights or candle lights?

8. Pillow fights or ghost stories?

9. Indoor picnic or make pizzas?

10. Pajamas or oversized T-shirts?

11. Karaoke or dance-off?

12. Truth or dare or spin the bottle?

13. Popcorn or nachos?

14. Sleep early or pull an all-nighter?

15. Face masks or nail painting?

16. Order in or cook together?

17. Home video or photo slideshow?

18. Junk food or healthy snacks?

19. Wine night or cocktail night?

20. Cooking contest or baking contest?

21. Storytelling or movie marathon?

22. Take selfies or make a fun video?

23. Hot chocolate or cold soda?

24. Bonfire or barbecue?

25. Horror stories or funny anecdotes?

26. Roasting marshmallows or baking s’mores?

27. Twister or charades?

28. Build a fort or have a tea party?

29. Listen to music or watch music videos?

30. Watch the sunrise or sleep in?

31. Tacos or burgers?

32. Scavenger hunt or hide and seek?

33. Dance party or sing-along?

34. Romantic movies or sci-fi movies?

35. Chocolates or gummies?

36. Ice cream sundae or fruit salad?

37. Homemade popcorn or store-bought?

38. Pizza delivery or Chinese takeout?

39. Indoor tent or sleeping bags?

40. Build a blanket fort or pillow castle?

41. Making TikToks or watching YouTube?

Philosophical This or That questions

Ready to get your brain gears grinding? There’s no better way to do that than by diving into some philosophical This or That questions. They’re not just for the ivory tower folks, they’re for anyone who enjoys pondering the big and often complicated questions about life, the universe, and everything in between. But don’t worry, you don’t need a philosophy degree for these. They’re just meant to get you and your friends talking, thinking, and maybe seeing the world from a different perspective.

1. Fate or free will?

2. Idealist or realist?

3. Knowledge or wisdom?

4. Passion or stability?

5. Quality of life or quantity of life?

6. Nihilism or existentialism?

7. Objective truth or subjective truth?

8. Practicality or morality?

9. Mind or body?

10. Conformity or rebellion?

11. Logic or emotion?

12. Experience or innocence?

13. Survival or sacrifice?

14. Heroes or villains?

15. Art or science?

16. Dreams or goals?

17. Time or space?

18. Privacy or security?

19. Equality or equity?

20. Nature or nurture?

21. Chaos or order?

22. Justice or mercy?

23. Spirituality or materialism?

24. Culture or nature?

25. Simplicity or complexity?

26. Doubt or belief?

27. Selfishness or selflessness?

28. Tradition or innovation?

29. Individualism or collectivism?

30. Cynicism or optimism?

31. The journey or the destination?

32. Fame or privacy?

33. Facts or theories?

34. Creation or destruction?

35. Control or freedom?

36. Humility or pride?

37. Progress or preservation?

38. Rights or responsibilities?

39. Knowledge or imagination?

40. Achievement or potential?

41. Courage or caution?

42. Power or respect?

43. Certainty or mystery?

If you are on a really philosophical vibe, you might want to try some of these philosophical questions to discuss with friends.

This or That questions to ask your friend’s crush or partner

Got the task of vetting your friend’s new squeeze? Or maybe you’re just trying to get to know them better. No matter what the case, we’ve got you covered with some interesting This or That questions that will help you break the ice and learn more about them. These questions are a mix of fun, serious, and thoughtful, aiming to give you a rounded picture of who they are. Keep in mind that the aim here isn’t to grill them, but to engage in a fun and friendly chat.

1. Music concert or movie theater?

2. Homecooked meals or restaurant dining?

3. Long walks or long drives?

4. Museum or amusement park?

5. Candlelit dinner or backyard barbecue?

6. Comedy show or music festival?

7. Camping or glamping?

8. Netflix and chill or night out on the town?

9. Coffee date or cocktail date?

10. Brunch date or dinner date?

11. Big city or small town?

12. Romantic dinner or adventurous outing?

13. Classic movie or new release?

14. Morning jog or evening walk?

15. Thrift shopping or brand shopping?

16. Board games or video games?

17. Handwritten letter or email?

18. Wine tasting or beer sampling?

19. Stay in or go out?

20. Dancing or singing?

21. Working out or chilling out?

22. Indoor date or outdoor date?

23. Summer or winter?

24. Adventurous trip or relaxing vacation?

25. Early bird or night owl?

26. Poetry reading or book club?

27. Star gazing or cloud watching?

28. Chocolates or flowers?

29. Romantic comedy or action thriller?

30. Road trip or plane trip?

31. Dress up or dress down?

32. Spontaneous plan or scheduled plan?

33. Breakfast in bed or dinner for two?

34. Sightseeing or relaxing?

35. Live theater or live sports?

36. DIY gift or store-bought gift?

37. City skyline or countryside view?

38. Soft music or loud music?

39. Vintage style or modern style?

Fun This or That questions

Let’s shake things up with some This or That questions designed to lighten the mood, spark laughter, and keep the conversation flowing. Some of these questions are silly, others might catch you off guard, but they’re all guaranteed to get some grins. So, whether you’re out for drinks, chilling at home, or simply stuck in a group chat, try tossing a few of these fun questions into the mix.

1. Pirate or Ninja?

2. Time travel or space travel?

3. Be invisible or be invincible?

4. Be a kid your whole life or an adult your whole life?

5. Toilet paper over or under?

6. Have a third eye or a third arm?

7. Super strength or super speed?

8. Have a pet dinosaur or a pet dragon?

9. Always wear clown shoes or always wear a big red nose?

10. Be a professional joke teller or a professional stunt person?

11. Sleep in a bed of marshmallows or a bed of popcorn?

12. Have feet for hands or hands for feet?

13. Be able to breathe underwater or survive in space without a suit?

14. Be a superhero or a supervillain?

15. Ketchup or mustard?

16. Always wear a top hat or a clown nose?

17. Be a famous actor or a famous singer?

18. Be a centaur or a mermaid/merman?

19. Have a rewind button or a pause button for your life?

20. Have a pet unicorn or a pet pegasus?

21. Only be able to whisper or only be able to shout?

22. Only use a fork (no spoon) or only use a spoon (no fork)?

23. Be best friends with Harry Potter or Sherlock Holmes?

24. Have a tail or an extra arm?

25. Be a robot or an alien?

26. Have a house made of candy or a house made of pizza?

27. 80s fashion or 90s fashion?

28. Have the ability to read minds or to become invisible at will?

29. Be a part of the Friends cast or The Office cast?

30. Have a time machine or a magic wand?

31. Always have to sing rather than speak or dance everywhere you go?

32. Know all languages or be able to speak with animals?

33. Unlimited sushi for life or unlimited tacos for life?

34. Be a famous writer or a famous scientist?

35. Telepathy or teleportation?

36. Batman or Superman?

37. Swim in a pool full of Nutella or a pool full of maple syrup?

38. Only eat tacos for a year or only eat pizza for a year?

39. Have your head the size of a tennis ball or the size of a watermelon?

40. Live in a world of Star Wars or Lord of the Rings?

41. Eat only hot food or only cold food?

42. Be fluent in all languages or able to play all instruments?

43. Have a permanently clogged nose or a piece of green food always stuck in your teeth?

44. Be a giant hamster or a tiny rhino?

45. Have a pet talking parrot or a pet talking monkey?

Of course, you don’t need to be limited to This or That questions to have fun conversations. Keep the fun flowing with this list of questions to enjoy your time with friends.

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages SocialSelf’s scientific review board. Follow on Twitter or read more.

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