100 This or That Questions to Get a Conversation Going

Read a question aloud and let everyone choose. Invite an explanation, but make it optional. “Neither” is a fair answer, and anyone can pass without giving a reason. Use the bold questions for a quick round; add the follow-ups when a choice gets people talking.

Food and Kitchen

1. Pizza or tacos? Build your ideal version, toppings included. Notice who starts reconsidering once someone describes theirs.
2. Sweet breakfast or savory breakfast? Give your full diner order, including the side dish you refuse to leave off.
3. Cook at home or order in? Answer for an ordinary weeknight first, then for an evening when you have plenty of time.
4. Fries or onion rings? Does the dipping sauce change your vote, or is your loyalty to the side dish itself?
5. Ice cream in a cone or in a cup? Cone fans get an edible container. Cup fans get to concentrate on the ice cream.
6. Crispy cookies or chewy cookies? Name the cookie that makes the strongest case for your side, preferably with a very specific description.
7. Pancakes or waffles? Waffle fans will probably mention the squares that hold the syrup. Pancake fans, your response?
8. Spicy or mild? Which dish suits your preference best? You can love a little heat without wanting it in every meal.
9. Popcorn or candy at the movies? The next question is whether your snack makes it past the previews.
10. Leftover pizza: cold or reheated? Does the topping matter, or do you have one firm rule for every slice?
11. A new restaurant or an old favorite? Name the familiar order that could persuade you to stop looking at new menus.
12. Cake or pie? Pick a flavor, too. Lemon cake versus apple pie is a different discussion from chocolate cake versus cherry pie.

Home and Everyday Habits

The most ordinary preferences can produce surprisingly detailed explanations. Someone at the table may have an entire system for the alarm clock.

13. Early bird or night owl? What would you do with an uninterrupted hour at your favorite time of day?
14. Text or call? Does your answer change for a quick practical question versus good news you can’t wait to share?
15. Paper calendar or phone calendar? Describe the reminder system that actually gets you to an appointment on the right day.
16. Make the bed every morning or leave it? Bed-makers can explain whether vacation changes the rule. Everyone else can enjoy having one fewer task.
17. Hot weather or cold weather? Name your ideal temperature. The two sides may turn out to be only five degrees apart.
18. Fan on or fan off while you sleep? If you’re a fan person, is it about the breeze, the sound, or both?
19. Slippers or socks around the house? Barefoot voters can declare a third team. What makes your choice the most comfortable?
20. Phone on loud or on silent? Are there people or situations that get an exception to your usual setting?
21. Read the instructions first or figure it out as you go? This is an excellent opening for a furniture-assembly story, if anyone has one.
22. Wash the dishes right away or after the show? Does cooking something elaborate change your answer, or make you even more committed to it?
23. Clean a little every day or do one big cleanup? Choose the one chore you’d most happily hand off forever.
24. Get up at the first alarm or hit snooze? What alarm sound would you retire permanently if you could?

Travel and Getaways

Answer from experience or invent your ideal trip. Having visited the place is not a requirement.

25. Beach or mountains? Describe the first hour after you arrive. Are you already exploring, or finding somewhere comfortable to sit?
26. Window seat or aisle seat? Make the case for your choice on a long trip, when the trade-offs become harder to ignore.
27. Road trip or flight? What would make the drive worth it: scenery, stops along the way, or the company?
28. Plan every stop or leave the itinerary open? Name one part of a trip you would always arrange ahead of time.
29. Big city or small town? Pick a place you’d like to visit, then describe how you’d spend an afternoon there.
30. Hotel room or tent? What’s the one comfort you’d want either way? Be as particular about the pillow as you like.
31. Pack a week early or the morning you leave? Middle-ground packers can choose the option they’d find easier to live with.
32. Souvenirs or photos? Share an example of something you brought home—or a picture you took—that still makes you smile.
33. Sunrise view or sunset view? Choose the setting: a city rooftop, a quiet shore, a mountain overlook, or somewhere else entirely.
34. Travel with a group or with one other person? What activity would be better with your chosen number of travel companions?
35. Road-trip snacks: salty or sweet? Name your first pick at a rest stop, then nominate something from the other side to go with it.
36. Theme park or national park? Describe the attraction or scenery that would make you eager to get there.

Weekends and Free Time

37. Board games or card games? Recommend the game you’d teach a new friend first, including how patient they’d need to be during the explanation.
38. Stay in or go out? Give your choice a proper plan. “Out” could mean a crowded event or a walk to get dessert.
39. Matinee or late show? Is the movie the main event, or do you like building the rest of the day around it?
40. Farmers market or flea market? Tell the group what you would hope to find, even if you were supposedly “just looking.”
41. Jigsaw puzzle or video game? Would you rather tackle it alone, work together, or have someone nearby offering highly questionable advice?
42. Picnic or dinner on a patio? Design the menu. Picnic voters may also want to nominate someone other than themselves to carry the basket.
43. Learn an instrument or learn a language? Name your choice and the first song you’d play or conversation you’d want to have.
44. Spend the afternoon gardening or baking? What would you grow or make first if the supplies were already waiting for you?
45. Bowling or mini golf? Which would you choose for a group of enthusiastic beginners, and what would make the outing fun?
46. Backyard games or a walk around the neighborhood? Pick a game or a route you’d enjoy sharing with the group.
47. Visit a museum or watch a live game? Which exhibit or sport would make you put the date on your calendar?
48. A rainy day indoors or a snowy day outside? Describe one activity that would make your chosen day feel well spent.

Entertainment and Pop Culture

Titles and recommendations are welcome, but keep plot twists out of the discussion until everyone agrees to hear them.

49. Reality competition or scripted drama? Pitch a favorite show in one sentence, as if you’re choosing what the whole group watches next.
50. Comedy or mystery? Would you rather remember a story for how much you laughed or how cleverly it surprised you?
51. Watch the whole season at once or one episode at a time? What kind of ending makes stopping especially difficult?
52. Reread a favorite book or rewatch a favorite show? Name the title you return to and what keeps bringing you back.
53. Sing along in the car or keep it quiet? Is there a song that could persuade you to switch sides?
54. Live concert or musical theater? Pick the performer or production you’d most like to see, with an imaginary ticket already in hand.
55. Podcasts or music? Share one recommendation and the occasion it suits best: cooking, walking, commuting, or doing absolutely nothing.
56. Spoilers: want them or avoid them? Explain your preference without revealing an actual ending. The spoiler-avoiders are trusting you here.
57. Animated movie or live action? Which story would you like to see made in your preferred format?
58. Read the book first or watch the movie first? Talk about what you enjoy comparing afterward, without giving away the plot.
59. Karaoke: lead singer or backup? Would your choice change if a few close friends were singing with you?
60. Game show contestant or studio audience? Choose the show. Contestant voters can name their strongest category; audience voters can enjoy the lack of a buzzer.

Hypotheticals and Impossible Choices

For this round, impossible logistics are somebody else’s problem. Pick the option you’d most enjoy imagining.

61. Fly or teleport? Choose your first destination, then explain whether getting there instantly would beat enjoying the view along the way.
62. Talk to animals or speak every human language? Who would you want your very first conversation to be with?
63. Visit the past or the future? Pick a year and one ordinary thing you’d be curious to see there.
64. Live in a treehouse or a houseboat? Describe the view from your favorite chair and one feature your unusual home would need.
65. A personal chef or a personal driver? What would you request on day one: a particular meal or a particular outing?
66. Summer forever or autumn forever? Name the seasonal pleasure that wins your vote. Spring and winter fans can register an official protest.
67. A walk-on movie role or a voice role in an animated film? Invent the character you’d like to play.
68. Pause time or rewind ten seconds? Which would be more useful during an ordinary Tuesday? Keep your example as wonderfully unremarkable as you like.
69. A self-cleaning kitchen or a closet that folds and puts away laundry? Describe what you’d do while your imaginary invention handled the work.
70. A pet dragon or a pet unicorn? Assume both are friendly. Your first responsibility is to come up with a suitable name.
71. Never wait in line again or never sit in traffic again? Name the outing this would improve the most.
72. Know every song lyric or every movie quote? Pick the song or movie you’d finally be able to get right from start to finish.

Personality and Preferences

These invite a little more explanation. Keep them as light or as thoughtful as the group prefers.

73. Spend your downtime alone or with people? Describe an ideal evening after a week when you’ve been especially busy.
74. Give advice or ask for it? Name an everyday subject where you’d happily do either, such as recipes, books, or organizing a closet.
75. Lead the group or support the leader? Think of a casual project or outing. Which part would you most enjoy handling?
76. Remember names or remember faces? If you have a useful trick for learning someone’s name, this is a good time to share it.
77. Arrive early or right on time? How early counts as early to you, and what do you do with the spare minutes?
78. Eat the best bite first or save it for last? Describe a food that makes this decision especially important.
79. Tell the story or listen to it? What kind of story always gets your attention, regardless of which role you usually prefer?
80. A handwritten thank-you note or a thank-you text? Are there occasions when you’d especially appreciate one over the other?
81. Show appreciation with a favor or with words? Offer an everyday example of something you’d like to do for a friend.
82. Win the game or have the funniest moment? Is there a memorable game-night moment that explains why you picked your answer?
83. Save old keepsakes or clear things out regularly? Choose one object that would survive a cleanup no matter which side you’re on.
84. Finish one project or start three at once? Describe the kind of project most likely to hold your attention from beginning to end.

Growing Up

Share a memory or answer as your younger self might have. Nobody needs a matching childhood experience to join in.

85. Recess or lunch? Was the attraction a favorite game, a favorite food, or getting to sit beside a particular friend?
86. Saturday morning cartoons or after-school snacks? Name the cartoon or snack that makes your choice feel obvious.
87. Summer camp or summer at home? Design one perfect summer afternoon for your younger self, using either setting.
88. Field trip or class party? Pick a destination or party activity you would have been excited to hear announced.
89. Building forts or riding bikes? Describe your finest construction or a favorite place to ride, if a memory comes to mind.
90. A sleepover at your house or at a friend’s? What snack, game, or movie would have made the evening complete?
91. Lemonade stand or bake sale? Invent your menu and the name of your operation. Dramatic business names are welcome.
92. Sidewalk chalk or a box of crayons? What would you have drawn first with a fresh supply and a whole afternoon?

Celebrations and Gifts

93. A surprise party or a celebration you plan yourself? Describe the kind of gathering you’d actually enjoy attending.
94. Wrap gifts neatly or use gift bags? Is the presentation part of the fun for you, or mainly the final obstacle before giving the gift?
95. Celebrate a birthday for one day or the whole week? Week-long celebrators can explain what happens on an otherwise ordinary Wednesday.
96. Give gifts or receive gifts? Think of a gift that was fun to choose or especially pleasant to receive.
97. A sit-down holiday dinner or a help-yourself buffet? Name the dish you’d look for first, whichever serving style you chose.
98. Handmade gift or store-bought gift? Give an example of either that would suit you particularly well. Practical answers are welcome.
99. A photo booth or a table of party games? Which would you visit first as a guest, and what would persuade you to stay?
100. Host the next game night or be a guest? Either way, name the game you’d be delighted to see on the table.

Five More Ways to Play

The read-and-answer version needs no supplies. These variations add prediction, friendly debate, movement, speed, or a little randomness. Choose one rather than explaining every possible format before anyone gets to play.

Predict the Player

Choose one willing person as the featured player. Read a question, and have that player write their choice without showing it. Everyone else writes a prediction. Reveal together; each matching prediction earns one point. For this version, the featured player chooses one of the two options or passes so the reader can choose a replacement.

Give each featured player three answered questions, then offer the role to the next person. Anyone can skip guessing or decline the featured-player role. Finish once everyone who wants a turn has had one; the highest prediction total wins. The fun is in discovering the unexpected choice, rather than challenging someone to prove they meant it.

Defend Your Pick

Two volunteers take opposite sides of a question. They can choose their sides or flip a coin to assign them; their real preferences don’t have to match. Give each person thirty seconds to make a case, then invite the rest of the group to vote for the argument they enjoyed most.

Keep the arguments about the options, rather than the people who prefer them. “A cup won’t drip on your shoes” is fair advocacy. Making fun of cone voters isn’t. After the vote, invite another pair of volunteers. Cold pizza, waffles, and gift bags all have promising legal teams waiting to happen.

Split the Room

Assign one side of the room to the first option and the opposite side to the second. Players walk to their choice, or point from their seats. Leave room for people to move comfortably, and keep moving optional.

Invite one volunteer from each side to explain their vote. Players choosing neither can stay in the middle or keep their hands down. This version makes the split visible at once, without requiring everyone to take an individual speaking turn.

Lightning Round

Read ten questions in a row and have players answer with their option only. Skip explanations for now, but allow passes as usual. Once the ten are finished, return to the question with the most surprising split and open it up for discussion.

Letting everyone answer together keeps this lively. If the room gets too loud to hear the choices, go around the table instead. There’s no elimination for hesitating; the speed is there to keep the round moving.

The Question Bowl

Write ten or twenty question numbers on slips of paper and put them in a bowl. Players take turns drawing a number, and the reader looks it up. Set used slips aside so questions don’t repeat.

This scrambles the topics without requiring you to copy out the questions. A pet dragon might follow a dishwashing preference, which gives the evening a pleasantly unpredictable rhythm. Add more numbered slips if the group wants to continue.

Ready-Made Rounds

Each set below uses questions from the numbered list. Read the bold question first and save its follow-up for a choice the group wants to discuss.

• Mixed ages: 1, 7, 25, 41, 62, 70, 85, 89, 92, and 99. A mix of food, imagination, and familiar activities.
• New friends or coworkers: 2, 11, 29, 37, 40, 43, 49, 55, 60, and 77. These leave room for recommendations without requiring a personal story.
• Predict the Player with close friends: 3, 14, 16, 20, 26, 51, 56, 78, 84, and 96. Use these as a starting pool and read any replacements from the same sections.
• Defend Your Pick: 5, 7, 10, 21, 58, and 94. Everyday choices with enough practical detail to support a friendly argument.
• Ten-question lightning round: 4, 6, 12, 17, 25, 43, 61, 63, 66, and 70. Read the options only, then revisit whichever answer deserves an explanation.

Keep the Conversation Moving

Follow an interesting answer. If someone chooses a flea market because they’re hunting for an old board game, ask about that game. The printed follow-up can wait. A specific detail someone offers is often a better next step than another prepared question.

Invite another view without staging a contest. Try, “Who picked the other option?” or “Does anyone’s answer change on vacation?” People can compare preferences without reaching a verdict. A unanimous answer can be interesting, too; find out whether everyone chose it for the same reason.

Leave room for quieter players. In an unscored round, go around the table occasionally so the fastest answer doesn’t always take over. Accept a short answer and move along without turning it into an interview.

Let a good tangent happen. If a question leads to a story people want to hear, stay with it. If the conversation runs out, read the next choice. Finishing all one hundred questions isn’t the assignment for your guests.