301 This or That Questions for Friends, From Funny to Deep

If you’re getting to know someone new or you have social anxiety — or you’re getting to know someone new while also having social anxiety — sometimes you need a conversation warmup. “This or That” questions are great for those moments. And they’re just as fun for best friends who think they already know everything about each other, too!

This or That game questions feel simple, given you only have two options to choose from. But don’t let that fool you — you’d be surprised by the number of side tangents that spring up while playing (as in: “What do you mean you’d rather live inside a Hallmark Christmas movie than get to be a Disney villain?!”). And those side tangents are half the fun! Best case scenario, some answers to these prompts will spin out into full-blown stories about each other’s life experiences, taking you from silly icebreaker territory to budding (or deepening) friendship. Who knows what you’ll learn!

Need a refresher on how to play This or That before diving in? There’s only one rule: No matter how embarrassing or hard the question is, you have to pick one. (That means no “I choose both!” cop-outs either.) It’s a game that can be played with however many people you’ve got on hand, but we like sticking to smaller groups or, honestly, to one-on-one sessions. That’s where you can really get into the personal, weird stuff. No matter how many people you’re playing with, just make sure everyone knows not to overthink their answers. As with Would You Rather and 21 Questions, this game is best when responses are off-the-cuff and unrehearsed. If you’re playing with indecisive pals (or if you are that pal), you may even want to set a timer!

So, whether you’re looking to pass the time with your day-one besties or you’re hoping to get to know a new friend better, we’ve rounded up the best This or That questions across all kinds of categories, from funny and insightful to downright strange. Playing This or That with a friend who’s also a crush? We’ve added in some juicy This or That relationship and dating questions to help you discreetly take things up a level. (You’re welcome.) You could always pull from our list of This or That questions for couples, too.

Let the conversation starters begin!

This or That Questions: Funny

1. Iced coffee on a snowy day or hot coffee in a heatwave?
2. Sandals with socks or crocs with a going-out outfit?
3. Toe socks or toe rings?
4. Burping or farting?
5. Being super sweaty in cold weather or having a cold in hot weather?
6. Bad haircut or bad dye job?
7. Accidentally liking your crush’s circa-2015 selfie or wearing a Viking helmet for a week?
8. Pets who can talk or babies who can talk?
9. Mistaken lyrics or misquoted movies?
10. Chicken pox or poison ivy?
11. Be stuck in an elevator with your ex and their new partner or with your current partner and their ex
12. Dating a clown or dating a magician?
13. Battling zombies or vampires?
14. Singing poorly or speaking too loud all the time?
15. Stranded on an island full of fruit or lost in a city full of your favorite animal?
16. Successful blind date with your crush or blind date fail with your celebrity crush?
17. Have to wear a chicken costume to your first day of work or have your parents chaperone your next date?
18. Accidentally like your ex’s old vacation photo or mistakenly send a heart emoji to your boss?
19. Get married at Disney World or in Las Vegas?
20. Have your dating app messages leaked online or have your search history made public?
21. Have a pet dragon the size of a cat or a cat the size of a dragon?
22. Have spaghetti for hair or marshmallows for teeth?
23. Mullet haircut or bowl cut?
24. Eat pizza with pineapple or cereal with water?
25. Only use flip phones or only watch black-and-white TV?
26. Always have wet socks or always have cold hands?
27. Only be able to text in emojis or only be able to text in acronyms?
28. Be able to talk to animals but they constantly give you unsolicited advice or be able to fly but only at walking speed?
29. Loud neighbors or nosey neighbors?
30. Have a permanent duck face in all photos or only be able to type with one finger?
31. Have to sleep hanging upside down like a bat or standing up like a horse?
32. Only be able to eat foods that are blue or drinks that are green?

This or That Questions: Pop Culture

1. Be the third wheel on a date with Tom Holland and Zendaya or Lucy Dacus and Julien Baker?
2. Folklore or Evermore?
3. Waiting in the concert merch line or seeing the opener?
4. Friends or Seinfeld?
5. Fiction or non-fiction?
6. Chappell Roan or Sabrina Carpenter?
7. One Direction or Jonas Brothers?
8. The book or the movie adaptation?
9. Pop music or rock music?
10. Taylor Swift or Britney Spears?
11. Meet Lady Gaga or Beyoncé?
12. Eddie Munson or Steve Harrington?
13. Encanto or Turning Red?
14. Harry Potter or Lord of the Rings?
15. To All The Boys I’ve Loved Before or The Summer I Turned Pretty?
16. Emma Chamberlain or Addison Rae?
17. Attend Coachella or the Met Gala?
18. Be the guest judge on RuPaul’s Drag Race or get styled by Law Roach?
19. The Kardashians or the D’Amelios?
20. Podcast or audiobook?
21. Twitch or YouTube?
22. HBO Max or Hulu?
23. Star in a remake of The Lizzie McGuire Movie or The Princess Diaries?
24. Horror movies or rom-coms?
25. Comedy or drama?
26. Xbox or PlayStation?
27. The Harry Potter trio or the Stranger Things kids?
28. Reality TV shows or scripted programs?
29. Madonna or Cher?
30. Go on tour with Olivia Rodrigo or star in a rom-com with Jacob Elordi?
31. Marvel or DC comics?
32. Cartoons or soap operas?
33. Go backstage with Dua Lipa or babysit for the Biebers?
34. Be in a rom-com directed by Greta Gerwig or a buzzy A24 drama?

Random This or That Questions

1. Only be able to take cold showers or have to sleep without a blanket every night?
2. Be able to teleport or read minds?
3. Only be able to use a flip phone or have to carry a boombox for music?
4. Shower or bath?
5. ’80s or ’90s?
6. Board games or video games?
7. Rich and famous or rich and unknown?
8. Art museum or history museum?
9. Sunrise or sunset?
10. Physical planners or digital planners?
11. Dogs or cats?
12. Being on time or being late?
13. Being too hot or being too cold?
14. Saturday or Sunday?
15. A+ on a hard test or a week of no homework?
16. Tinder or Hinge?
17. Yoga or CrossFit?
18. Call or text?
19. Surfboard or skateboard?
20. Losing sleep or skipping a meal?
21. Animals or people?
22. A career as a doctor or a pilot?
23. Movie night or a night out?
24. Spring or fall?
25. Pilates or running?
26. Notebook or Notes app?
27. Roller coasters or bumper cars?
28. Sleep in or stay up?
29. Sand or snow?
30. Influencers or celebrities?
31. Ocean or lake?
32. Play cards or crossword puzzles?
33. Convertible or sleeper van?
34. Snap or TikTok?
35. Shopping online or in-store?
36. Plants or pets?
37. AirPods or wire headphones?
38. General admission or assigned seats?
39. Bus or train?
40. Park hang or beach hang?
41. Shoes or bare feet?
42. Washing the dishes immediately or waiting until the sink is full?
43. BookTok or PlantTok?
44. Small group or big party?
45. Game night or movie night?
46. Truth or dare?
47. Pottery class or sewing class?
48. Android or iPhone?
49. Theme park or botanical garden?
50. Typing or handwriting?
51. Swimming in the ocean or swimming in a pool?

This or That Food Questions

1. Sparkling water or still water?
2. Orange slices or orange juice?
3. Sweet or salty?
4. McDonald’s or Taco Bell?
5. Cooking or baking?
6. Breakfast burrito or Bacon, egg, and cheese sandwich?
7. Bagel or doughnut?
8. Cheesecake or brownie?
9. Deep-dish pizza or thin-crust pizza?
10. Breakfast or dinner?
11. Sushi or burgers?
12. Peas or brussels sprouts?
13. Thanksgiving pies or holiday cookies?
14. Black coffee or milky coffee?
15. Skinny French fries or thick-cut wedges?
16. Dark chocolate or white chocolate?
17. Hot dog or hamburger?
18. Sour cream or guacamole?
19. Fried rice or lo mein?
20. Pie or cake?
21. Iced tea or iced coffee?
22. Ice cream sandwich or popsicle?
23. Chicken nuggets or chicken strips?
24. Pepsi or Coke?
25. Milkshakes or smoothies?
26. Pasta or pizza?
27. Potato chips or pretzels?
28. Red sauce or alfredo sauce?
29. Ramen or pho?
30. Cereal or oatmeal?
31. Food truck or eating in a restaurant?
32. Birthday cake or ice cream?
33. Sweet or sour?
34. Fruits or vegetables?
35. Pancakes or waffles?
36. Cooking or take-out?
37. Ice cream cone or ice cream in a cup?
38. Ketchup or mustard?
39. BBQ sauce or ranch dressing?
40. Pineapple on pizza: yes or no?
41. Tater tots or fries?
42. Crispy bacon or chewy bacon?
43. Cranberry sauce: jellied or whole berry?
44. Churros or beignets?
45. Chicken and waffles or biscuits and gravy?
46. Candy or popcorn at the movies?

This or That Travel Questions

1. Take a friend on your family vacation or join their family vacation?
2. East coast or west coast?
3. Vacation or staycation?
4. Passenger or driver?
5. Window seat or aisle seat?
6. Countryside or city?
7. Beach or forest?
8. Road trip or direct flight?
9. Cabana or cabin?
10. Safari in Kenya or snorkeling in the Great Barrier Reef?
11. Skiing in the Swiss Alps or sunbathing in the Maldives?
12. Shopping in New York City or exploring markets in Marrakech?
13. Oktoberfest in Germany or Carnival in Brazil?
14. Touring castles in Scotland or temples in Thailand?
15. Visit the Sydney Opera House or the Hollywood Walk of Fame?
16. Eiffel Tower or the Statue of Liberty?
17. Luxury hotel or budget hostel?
18. Travel with a strict itinerary or go with the flow?
19. Visit a new destination every time or revisit favorite places?
20. Travel for adventure or relaxation?
21. Visit tourist hotspots or hidden gems?
22. Travel with checked luggage or carry-on only?
23. Get to know one place or hop between multiple destinations?
24. Guided tours or explore independently?
25. Cold climates or warm climates?
26. Travel for cultural experiences or outdoor adventures?
27. Explore the fjords of Norway or the glaciers of Patagonia?
28. Experience Diwali in India or Chinese New Year in Beijing?
29. Dive with sharks in South Africa or swim with dolphins in the Bahamas?
30. Red-eye flight or layover?
31. Take a cooking class in Italy or a dance class in Spain?
32. One big, expensive vacation per year or multiple short, cheaper ones?
33. Budget every day while traveling or look at the credit card when you get home?

This or That Style Questions

1. Maximalism or minimalism?
2. Bangs or no bangs?
3. Bright colors or neutrals?
4. Cottagecore or coastal grandma?
5. Crop tops or oversized tops?
6. Lipstick or chapstick?
7. Flats or heels?
8. Fanny pack or tote bag?
9. Hair up or hair down?
10. Sparkle or matte?
11. Middle part or side part?
12. Studs or hoop earrings?
13. Wearing all gold/all silver jewelry or mixing metals?
14. Minimalist jewelry or chunky jewelry?
15. Long nails or short nails?
16. Long or short hair?
17. Vans or Converse?
18. Bright white sneakers or Doc Martens?
19. Rare Beauty or Kylie Cosmetics?
20. Sneakers or sandals?
21. Tattoos or piercings?
22. Jeans or sweats?
23. Cutting bangs in the bathroom or going to the salon?

Juicy This or That Questions

1. Younger or older?
2. Kiss on the first date or wait for a few dates?
3. Playing on the same team as your crush or on opposite teams?
4. Playful banter or deep, meaningful conversations?
5. Making the first move or waiting for them to initiate?
6. Giving a massage or receiving one?
7. Playful teasing or direct compliments?
8. Dominant energy or soft and sweet?
9. Dancing with a crush at a crowded club or a slow dance in private?
10. Flirting with touch or with words?
11. Kisses that start sweet or kisses that start bold?
12. Dirty talk or too busy to talk?
13. Them calling you “baby” or whispering your name?
14. Chasing or being chased?
15. Lust at first sight or slow burn chemistry?
16. Confess over text or face-to-face?
17. Flirt in their DMs: Why not or rather not?
18. Ask “what are we?” or keep it casual?
19. Friends-to-lovers or strangers-to-sparks?
20. Send them a risky text or an “oops” snap?
21. Play hard to get or easy to read?
22. Let them sleep over or sneak out after?
23. Catch a vibe or catch feelings?
24. Be someone’s secret: Been there or would never?
25. Soft and slow or fast and fiery?
26. Risk the friendship or risk never knowing?

Best This or That Questions That Get Real

1. Introvert or extrovert?
2. Glass half empty or glass half full?
3. Being embarrassed or being afraid?
4. Love or money?
5. Friends or family?
6. Silence or chatter?
7. A great playlist or a great book?
8. Save or spend?
9. Money or free time?
10. One best friend or a large group of friends?
11. Teamwork or solo project?
12. Travel to the past or the future?
13. Book smarts or street smarts?
14. Planning or spontaneity?
15. Live without music or live without movies?
16. Logic or emotion?
17. Skill or popularity?
18. Pause time or rewind time?
19. Talking or listening?
20. Telling a lie or being told a lie?
21. Forgiveness or justice?
22. Being challenged to be better or being accepted no matter what?
23. Truth that hurts or lie that soothes?
24. Be remembered or be at peace?
25. Be admired or be trusted?
26. Live for today or plan for tomorrow?
27. Live in one place forever or never settle anywhere?
28. Being certain or being curious?
29. Chase your dreams or build stability?
30. Fall in love fast or take your time?
31. Forgive and forget or remember and learn?
32. Chase peace or chase passion?
33. Be constantly evolving or finally content?
34. Always know the truth or always be happy?
35. Follow tradition or create your own way?
36. Private success or public recognition?
37. Be in control or let things flow?
38. Start something new or finish what you started?
39. Create beauty or create change?
40. Have more time or more energy?
41. Give second chances or move on?
42. Let people in or protect your peace?
43. Be independent or feel deeply supported?
44. Be brave or be wise?
45. Make your family proud or make yourself proud?
46. Trust easily or question everything?
47. Big wedding or elope?
48. Be the person who changes things or the person who holds things together?
49. Believe people can change or take them as they are?
50. Start again with a clean slate or carry the lessons forward
51. Have strong boundaries or open doors?
52. Listen to advice or trust your gut alone?
53. Be known for your resilience or your joy?
54. Stand for something or explore everything?
55. Act fast or wait it out?
56. Stand out or belong?