20 ChatGPT Prompts for This or That Questions (Fun, Easy, Endless)
Coffee or tea? Beach or mountains? This or that questions are the easiest game to start and the hardest to stop. Paste these prompts into ChatGPT, set the [brackets] for your crowd and vibe, and get an instant pile of either/or questions for couples, kids, parties, or your next post.
In short: This page contains 20 copy-paste ready prompts, organized into 5 categories with a description and pro tip for each. The first 5 prompts are free instantly, no signup needed. Hand-curated and tested by the AI Academy team.
Classic Fun
4 promptsAll-Rounder This or That
1/20✨ What it does
This prompt writes 20 this-or-that questions for [a party / a group / two friends] covering food, travel, lifestyle, and random preferences, each as A or B on its own line. Read them down the list, and let people in your group shout their pick with no extra speech.
You make fun social games. Write 20 "this or that" questions for [a party / a group / two friends] covering food, travel, lifestyle, and random preferences, easy for anyone to answer fast. Format each as "A or B" on its own line.
Pro tip: Ask for "20 more, weirder" once the easy ones run out.
Rapid-Fire Round
2/20✨ What it does
This prompt writes 25 quick-fire this-or-that questions for [group size] people, mixing everyday choices with a few surprises, both options short and punchy. Fire them off fast to your group, and do not let anyone explain until the round ends.
Write 25 quick-fire "this or that" questions for [group size] people designed to be fired off fast with no time to think, mixing everyday choices with a few surprising ones. Keep both options short and punchy.
Pro tip: Read them fast and don't let anyone explain their answer, it's funnier.
Hard Choices
3/20✨ What it does
This prompt writes 15 genuinely tough this-or-that questions about [topic] where both options are appealing or both are dreadful, covering food, life, and fun dilemmas. Make people in your circle defend the pick, then move on before it turns into a lecture.
Write 15 genuinely tough "this or that" questions about [topic] where both options are appealing or both are dreadful, so people actually have to think and defend their pick. Cover food, life, and fun dilemmas.
Pro tip: Ask people to explain these ones, the reasoning is the fun part.
Themed This or That
4/20✨ What it does
This prompt writes 20 this-or-that questions themed around [theme], each a simple A or B. Fill in the theme, then run them as a rapid round with hands in the air in your room.
Write 20 "this or that" questions all themed around [theme, e.g. food / travel / movies / seasons]. Keep them fun and relatable, each as a simple "A or B".
Pro tip: Name a niche theme your group loves for extra-relatable questions.
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For Couples
4 promptsCouples This or That
5/20✨ What it does
This prompt writes 20 this-or-that questions for a couple about each other and the relationship, mixing light preferences with sweet, revealing ones at a [cute / playful] level. Take turns answering with your partner, and notice where you disagree.
Write 20 "this or that" questions for a couple to answer about each other and their relationship, mixing lighthearted preferences with a few sweet, revealing ones. Keep them warm and fun, at a [cute / playful] level.
Pro tip: Take turns guessing your partner's answer before they say it.
Date Night Either/Or
6/20✨ What it does
This prompt writes 15 this-or-that questions for a date night with [name] that spark conversation about food, travel, and downtime, kept light and flirty. Ask them over dessert, and follow the ones that make you both talk longer.
Write 15 "this or that" questions perfect for a date night with [name], designed to spark conversation and learn each other's tastes in food, travel, and downtime. Keep the mood light and flirty.
Pro tip: Use these while waiting for food to arrive at a restaurant.
How Well Do You Know Me
7/20✨ What it does
This prompt writes 20 this-or-that questions for [name] and [name] to play how-well-do-you-know-me, where one guesses the other's pick, plus an easy score out of 20. Guess first, then reveal, and tally the score at the end of your round.
Write 20 "this or that" questions for a couple, [name] and [name], to play "how well do you know me", where one guesses the other's pick. Include an easy way to keep score out of 20.
Pro tip: Loser plans the next date, winner picks the movie.
New Relationship Questions
8/20✨ What it does
This prompt writes 15 fun this-or-that questions for a new couple covering tastes, habits, and lifestyle at a [mild / flirty] level, without pressure. Answer out loud with your partner, and treat mismatches as information, not a test.
Write 15 fun "this or that" questions for a new couple still getting to know each other, covering tastes, habits, and lifestyle, so they discover compatibility without pressure. Keep it playful at a [mild / flirty] level.
Pro tip: Add "nothing too serious yet" to keep it breezy.
For Kids
4 promptsKids This or That
9/20✨ What it does
This prompt writes 20 simple, silly this-or-that questions for kids aged [ages], using animals, snacks, and superpowers, each as A or B. Read them one by one to your kids, and let them hop to a side of the room if they want.
Write 20 "this or that" questions for kids aged [ages] using simple words and fun, silly choices they'll love, like animals, snacks, and superpowers. Format each as "A or B".
Pro tip: Great for the car, the dinner table, or a rainy afternoon.
Classroom This or That
10/20✨ What it does
This prompt writes 15 classroom-friendly this-or-that questions for students aged [ages] that get the class walking to one side of the room for each choice. Clear the space first, then call the two sides and let your students move.
Write 15 classroom-friendly "this or that" questions for students aged [ages] that get the whole class moving, where kids walk to one side of the room for each choice. Keep them inclusive and fun.
Pro tip: Ask for a version students answer by raising a hand or standing up.
Family Kids Round
11/20✨ What it does
This prompt writes 20 this-or-that questions the whole family can enjoy, easy enough for a [age]-year-old but fun for parents, mixing food, animals, holidays, and silly hypotheticals. Let the youngest pick first at your table, then go around.
Write 20 "this or that" questions the whole family can enjoy, easy enough for a [age]-year-old but fun for parents too. Mix food, animals, holidays, and silly hypotheticals.
Pro tip: Let the youngest read the questions to feel included.
Sleepover / Kids Party
12/20✨ What it does
This prompt writes 20 silly, kid-appropriate this-or-that questions for a sleepover or party with children aged [ages], like unicorn or dragon. Read them in the dark with a flashlight, and let giggles count as an answer from your kids.
Write 20 silly "this or that" questions for a kids sleepover or party with children aged [ages]. Make them giggly and imaginative, like "unicorn or dragon", and keep every option kid-appropriate.
Pro tip: Pair with a "run to this side of the room" rule to burn energy.
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Parties & Groups
4 promptsParty This or That
13/20✨ What it does
This prompt writes 25 fast, fun this-or-that questions for a party of [group size] adults that get the room talking and taking sides. Stand in the middle of your room, point to two walls, and make people move.
Write 25 "this or that" questions for a party of [group size] adults, mixing funny, relatable, and lightly debatable choices that get the room talking and taking sides. Keep them fast and fun.
Pro tip: Have people physically pick a side of the room for each one.
Team Icebreaker Version
14/20✨ What it does
This prompt writes 15 work-appropriate this-or-that questions for a quick icebreaker with [team size] coworkers, fun, not too personal, and answerable in one word. Go around once with your team, one word each, then start the meeting.
Write 15 work-appropriate "this or that" questions to use as a quick team icebreaker for [team size] coworkers. Keep them fun and safe, nothing too personal, each answerable in one word.
Pro tip: Run it as a poll so quiet coworkers can join without speaking up.
Debate Starters
15/20✨ What it does
This prompt writes 15 this-or-that questions that start a friendly argument at a party of [group size], with a one-line note on why each is divisive. Use the notes to pick the safest debates for your guests, then let people argue for thirty seconds each.
Write 15 "this or that" questions guaranteed to start a friendly argument at a party of [group size], like classic food and lifestyle debates people feel strongly about. Add a one-line note on why each is divisive.
Pro tip: Best played with a group that loves to argue for fun.
Get-to-Know-the-Group
16/20✨ What it does
This prompt writes 20 light this-or-that questions for a new group of [group size] people to learn personalities and find surprising things in common. Have everyone answer aloud, then call out the unexpected matches in your circle.
Write 20 "this or that" questions for a new group of [group size] people to quickly learn each other's personalities and find surprising things in common. Keep them light and easy to answer aloud.
Pro tip: Ask people to find one other person who matched all their answers.
Spicy vs Wholesome
4 promptsWholesome This or That
17/20✨ What it does
This prompt writes 20 wholesome, feel-good this-or-that questions about comfort, kindness, and simple joys for a gentle, all-ages [family night / classroom / gathering], each as A or B. Read them slowly, and let anyone in your group skip a pair they do not like.
Write 20 wholesome, feel-good "this or that" questions that are cozy and positive, about comfort, kindness, and simple joys. Perfect for a gentle, all-ages [family night / classroom / gathering]. Format each as "A or B".
Pro tip: Lovely for a slow evening, a family night, or a calm classroom.
Spicy Adult Round
18/20✨ What it does
This prompt writes 20 flirty, cheeky this-or-that questions for adults at a [couples / adults-only party] at a [mild / bold] spice level, kept playful and consensual. Set the spice first with your group, and drop any question someone is not comfortable with.
Write 20 flirty, cheeky "this or that" questions for adults at a [couples / adults-only party] at a [mild / bold] spice level. Keep them playful and consensual, never crude or offensive.
Pro tip: Set the spice level in the brackets and read the room first.
Social Media Post
19/20✨ What it does
This prompt writes 15 this-or-that questions for [Instagram Stories / TikTok / a poll] themed around [topic], plus a catchy caption. Post the caption with the first pair on your account, then add the rest as stickers or a follow-up.
Write 15 "this or that" questions designed for [Instagram Stories / TikTok / a poll] that get high engagement and easy taps, themed around [topic]. Suggest a catchy caption for the post too.
Pro tip: Ask for a matching sticker-poll layout idea for Stories.
Choose Your Own Spice
20/20✨ What it does
This prompt makes a this-or-that game for [group size] adults with 7 wholesome, 7 cheeky, and 7 spicy questions, clearly labeled so the group can pick how far to go. Vote on a level before you start, and stop if anyone wants to stay wholesome.
Make a "this or that" game with three escalating levels for [group size] adults: 7 wholesome, 7 cheeky, 7 spicy, clearly labeled, so the group can pick how far to go. Keep even the spicy ones tasteful and consensual.
Pro tip: Start at wholesome and only climb if everyone's comfortable.
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