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
1/20You 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.
A big, ready-to-read list of crowd-friendly either/or picks.
Pro tip: Ask for "20 more, weirder" once the easy ones run out.
Rapid-Fire Round
2/20Write 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.
A speed round built for instant gut-reaction answers.
Pro tip: Read them fast and don't let anyone explain their answer, it's funnier.
Hard Choices
3/20Write 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.
Dilemma-style picks that spark real debate.
Pro tip: Ask people to explain these ones, the reasoning is the fun part.
Themed This or That
4/20Write 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".
A single-theme set for a focused round.
Pro tip: Name a niche theme your group loves for extra-relatable questions.
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For Couples
4 promptsCouples This or That
5/20Write 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.
Either/or questions that spark laughs and little revelations.
Pro tip: Take turns guessing your partner's answer before they say it.
Date Night Either/Or
6/20Write 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.
Date-night picks that double as conversation starters.
Pro tip: Use these while waiting for food to arrive at a restaurant.
How Well Do You Know Me
7/20Write 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.
A guessing-game format that tests how well you know each other.
Pro tip: Loser plans the next date, winner picks the movie.
New Relationship Questions
8/20Write 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.
Low-pressure picks for a couple in the early days.
Pro tip: Add "nothing too serious yet" to keep it breezy.
For Kids
4 promptsKids This or That
9/20Write 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".
Simple, silly picks perfectly pitched for young kids.
Pro tip: Great for the car, the dinner table, or a rainy afternoon.
Classroom This or That
10/20Write 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.
Move-around picks that turn a lesson into a game.
Pro tip: Ask for a version students answer by raising a hand or standing up.
Family Kids Round
11/20Write 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.
All-ages picks that keep kids and parents both playing.
Pro tip: Let the youngest read the questions to feel included.
Sleepover / Kids Party
12/20Write 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.
Giggle-inducing picks for a room full of kids.
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
13/20Write 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.
A party-sized set built to divide the room playfully.
Pro tip: Have people physically pick a side of the room for each one.
Team Icebreaker Version
14/20Write 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.
Office-safe either/or picks for a fast team warm-up.
Pro tip: Run it as a poll so quiet coworkers can join without speaking up.
Debate Starters
15/20Write 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.
Deliberately divisive picks that get everyone talking.
Pro tip: Best played with a group that loves to argue for fun.
Get-to-Know-the-Group
16/20Write 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.
Fast personality-revealing picks for a fresh group.
Pro tip: Ask people to find one other person who matched all their answers.
Spicy vs Wholesome
4 promptsWholesome This or That
17/20Write 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".
Cozy, positive picks for a warm, all-ages mood.
Pro tip: Lovely for a slow evening, a family night, or a calm classroom.
Spicy Adult Round
18/20Write 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.
Flirty either/or picks with a dial for how bold to go.
Pro tip: Set the spice level in the brackets and read the room first.
Social Media Post
19/20Write 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.
Scroll-stopping picks formatted for social engagement.
Pro tip: Ask for a matching sticker-poll layout idea for Stories.
Choose Your Own Spice
20/20Make 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.
A tiered set that lets the group control the intensity.
Pro tip: Start at wholesome and only climb if everyone's comfortable.
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