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This or That Questions That Actually Start an Argument (the Fun Kind)

This or that questions are the cheat code of conversation: no setup, no awkward pause, just two options and an instant opinion. Pineapple on pizza or a war crime? Window seat or aisle? They sound simple, but the good ones reveal exactly who you're dealing with — and start the kind of debate where everyone suddenly has a hill to die on.

The trick is that not all either-or questions are created equal. "Coffee or tea" is a yawn. "Coffee that tastes like regret or tea that tastes like disappointment" is a conversation. Below you'll find a big batch of the witty, specific kind — for parties, road trips, first dates, group chats, and that 11pm "I'm bored" text.

Quippy is an iOS app that deals these endlessly. Tap, get a card, force someone to choose. No printing, no repeats, no running dry at minute four — just a fresh this or that deck whenever the room goes quiet.

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01Be able to teleport anywhere but always land 10 feet in the air, or be invisible but only when nobody's looking?
02Always know when someone's lying, or always get away with lying yourself?
03Win every argument but lose every game, or win every game but lose every argument?
04Have a personal chef who only makes breakfast food, or a maid who only cleans on days you're home?
05Read minds but it's always the most boring thought, or talk to animals but they're all sarcastic?
06Have unlimited money but it's all in pennies, or unlimited free flights but only middle seats?
07Fight one horse-sized duck, or a hundred duck-sized horses (no take-backs)?
08Be 20 minutes early to everything forever, or 5 minutes late to everything forever?
09Have your search history read aloud at a funeral, or your texts read aloud at a wedding?
10Be famous for something embarrassing, or anonymous for something genuinely impressive?
11Re-live the same great year forever, or get a new mediocre year every time?
12Have a remote for life but it only rewinds 10 seconds, or one that only fast-forwards 10 seconds?
13Always have a slightly wet sock, or always have one earbud at 80% battery and the other dead?
14Date someone who corrects your grammar, or someone who narrates everything they do?
15Pineapple on pizza, or ranch on literally everything?
16Be the funniest person at a party nobody invited you to, or the most boring person everyone loves?
17Have every song stuck in your head be the chorus only, or the full song but slightly off-key?
18Live in a city that's always 10pm, or a town that's always 7am on a Sunday?
19Get a text back instantly but it's always 'k', or three days later but it's a heartfelt paragraph?
20Never feel hungover but always slightly hungry, or never feel hungry but always slightly hungover?
21Have a partner who steals the blanket, or one who sets six alarms and snoozes all of them?
22Be unforgettable to strangers, or invisible to everyone who already knows you?
23Win the lottery but have to tell everyone, or win half as much and tell no one?
24Have your inner monologue broadcast for one hour, or read everyone else's for one hour?

How to play this or that (and actually keep it fun)

Rules are gloriously simple: read the question, everyone picks a side, no abstaining and no "it depends." The fun lives in the follow-up — once someone commits, ask "why?" and watch a five-second answer turn into a ten-minute defense of putting milk in before the cereal.

For groups, make it a vote: count hands, then make the minority explain themselves. For one-on-one, alternate who asks. And keep the pace fast — this or that dies the moment it becomes a thoughtful seminar. The best round is twenty quick picks where two people end up genuinely offended over thermostat settings.

Best occasions for either-or questions

This or that is the most portable game on this list. At a party it's an instant icebreaker that doesn't require anyone to be clever on the spot — you just point at two options. On a road trip it fills the dead miles without anyone needing to look at a screen. On a first date it's low-stakes flirting: you learn if they're a planner or a chaos agent without interrogating them.

It's also perfect over text. Drop one in the group chat and you've got a 40-reply thread by lunch. Couples use the spicier ones to find out where their lines actually are. The format scales from "two coworkers in an elevator" to "twelve people three drinks in," which is why it never really gets old.

What makes a this or that question great

Specificity and stakes. "Beach or mountains" is fine; "a beach with a screaming toddler nearby or a mountain with no cell service" forces a real trade-off. The best ones either pit two goods against each other (so choosing hurts a little) or two evils (so everyone's miserable together) — the boring ones have an obvious right answer.

Quippy's decks lean into exactly that: oddly specific, slightly unhinged, occasionally personal. That's the difference between a question people answer and a question people argue about. When you want an endless supply that stays sharp instead of devolving into "cats or dogs," the app keeps dealing fresh cards so you never hit the bottom of the barrel.

FAQ

Frequently asked questions

What are this or that questions?

They're quick either-or questions that make you choose between two options — like "beach or mountains" or "text or call." The best ones are specific and have real stakes, so picking a side reveals something about you and kicks off a debate. They're a go-to for parties, road trips, dates, and group chats because there's zero setup.

What are some good this or that questions to ask?

Skip the obvious ones ("coffee or tea") and go for picks where both options sting or both are tempting — like "20 minutes early to everything or 5 minutes late forever?" or "read minds but it's always boring, or talk to animals but they're all sarcastic?" The whole sample list above is built from exactly this kind of question, and Quippy generates an endless supply.

Are these good for parties and big groups?

Yes — this or that is one of the easiest group games because nobody has to be clever on the spot, they just pick a side. Make it a vote, count hands, then make the minority defend themselves. It scales from two people in an elevator to a dozen people three drinks deep without losing momentum.

Do this or that questions work over text?

Perfectly. Drop one into a group chat and you'll have a 40-reply argument by lunch. They're short, they demand a reply, and they're low-effort to answer, which makes them ideal for keeping a conversation alive without writing essays. Quippy lets you pull a fresh one whenever the chat goes quiet.

How do I keep from running out of questions?

That's the exact problem Quippy solves. Instead of a static list you scroll past once, the app deals a fresh this or that card every tap and never repeats you into a corner. Free to play, with Pro ($69.99/yr, 3-day trial) unlocking every deck, unlimited AI, and custom decks you can build for your own crowd.

Is Quippy free?

Yes, you can play this or that and other decks for free. Pro is $69.99/year with a 3-day free trial and unlocks all decks — including spicy and couples — plus unlimited AI-generated questions and the ability to create custom decks tailored to your group. It's an iOS app.

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