A custom set of genuinely hard, funny, or deep 'would you rather' dilemmas — for road trips, parties, or kids.
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The prompt
Generate 'would you rather' questions.
The crowd: {{kids / adults / mixed / a couple}}
The vibe: {{silly / genuinely hard / deep / gross-out for kids / spicy for adults}}
How many: {{count}}
Give me questions that: 1) Are actually HARD to answer — real trade-offs, not obvious ones (a good 'would you rather' has no easy pick). 2) Match the crowd's vibe and stay appropriate for them. 3) Mix light and thought-provoking so it doesn't get samey. 4) Include a few that spark a story or debate, not just a one-word answer. Format numbered so I can read them out. Genuine dilemmas over easy picks.
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Why this works
A good 'would you rather' has no easy answer — the fun is the agonizing; generating real trade-offs instead of obvious picks is what turns it from a lull-filler into an actual debate.
Shared by Theo Brandt — Designer-dad. Prompts for the life admin nobody warned you about.
You are a speechwriter who specializes in toasts people quote at brunch the next day.
I'm toasting: {{who, and your relationship}}
Three real stories or details about them: {{messy fragments fine}}
The room: {{formal? rowdy? grandparents present?}}
Write a 2-minute toast (about 260 words):
1. Cold open — a line that gets a laugh in the first ten seconds. Not "for those who don't know me".
2. One story, told properly — with a detail so specific it could only be them.
3. The turn — where the laugh becomes a lump in the throat. One sentence of real feeling, earned by the story.
4. The raise — short, warm, glass up.
Rules: nothing that embarrasses anyone who didn't sign up for it, no inside jokes that exclude the room, no "webster's dictionary defines love".
You are a children's author who believes kids' ordinary days deserve epic retellings.
My kid: {{name, age}}
Something small they did or faced today: {{shared a toy, feared the dark, tried broccoli}}
Their current obsession: {{dinosaurs, space, a specific stuffed animal}}
Write tonight's story (about 400 words, for reading aloud):
1. {{name}} is the hero, in a world built from their obsession.
2. The plot mirrors today's small moment — transformed, never preachy. The lesson stays invisible.
3. One recurring silly phrase they'll want to say along with you.
4. A calm, sleepy ending — the last paragraph slows down on purpose, shorter sentences, softer words.
End with: "…and that's exactly how {{name}} saved the day."
Design a tabletop RPG one-shot I can run (or that you run for us).
System/vibe: {{D&D-style fantasy / sci-fi / cozy / horror-lite}}
Players: {{how many, experience level}} — Time: {{hours}}
Tone: {{heroic? funny? spooky? all-ages?}}
Build it: 1) THE HOOK — a one-paragraph setup that drops them into action fast. 2) THREE SCENES — a social one, a puzzle/exploration one, and a climax, each with what could go right or wrong. 3) MEMORABLE NPCs — 3 with a quirk and a want, easy to voice. 4) THE TWIST — one surprise that recontextualizes things. 5) FLEX POINTS — how to speed up or stretch to fit our time, and what to do if players go off-script. Fun and momentum over rules-lawyering.