100+ Yes or No Questions to Ask the Button

Staring at a blank text box is often the hardest part of using a random decision tool. You know you want an answer, but you cannot decide what to actually ask. This list exists to solve that specific problem: over 100 real yes or no questions, grouped into six everyday categories, each with a short note on when that kind of question tends to come up and why it is worth asking out loud instead of just turning it over in your head one more time.

This is a reference list for reading, browsing, and copying a question into the button when you need one. If you want something faster and more playful, the homepage has an interactive category picker where you tap a topic and a question fills in automatically. This page is the long-form version: more questions per category, and context for each one.

Why Keep a Ready-Made List of Questions

The hardest part of a decision is rarely the decision itself. It is figuring out how to phrase the question in a way that actually captures what you are stuck on. A vague worry like “I don’t know what to do about work” is nearly impossible to hand to a random generator. “Should I ask for a raise this quarter?” is not. Turning a fuzzy feeling into a specific yes-or-no question is most of the work, and having a list of proven phrasings on hand makes that step nearly instant. That is the whole value of a list like this one: it is a shortcut past the blank-page problem, not a replacement for thinking about what you actually want to ask.

Love & Relationships

Relationship questions tend to surface late at night or right before you send (or don’t send) a message. They work well with the button because the stakes of asking are usually much lower than they feel in the moment, and your emotional reaction to the answer is often more informative than the answer itself.

Should I text them first?
Is it time to have the talk?
Should I say yes to the date?
Do they like me back?
Should I forgive them?
Is this relationship worth fighting for?
Should I move in with them?
Is it time to let go?
Should I send that message?
Am I overthinking this?
Should I bring up how I’ve been feeling?
Is it too soon to say “I love you”?
Should I give them a second chance?
Should I ask about where this is going?
Should I plan something special for them this week?
Should I introduce them to my friends?
Should I be more honest about how I feel?

Work & Career

Career questions are usually decisions you have already half-made but have been sitting on. Asking the button is less about generating a career plan and more about noticing how you react when the decision is suddenly made for you, even temporarily.

Should I apply for that job?
Should I ask for a raise?
Is today the day I quit?
Should I start my own business?
Is this the right career path?
Should I take the promotion?
Should I negotiate the offer?
Is it time for a career change?
Should I go back to school?
Should I freelance full-time?
Should I speak up in the next meeting?
Should I ask my manager for feedback?
Is it time to update my resume?
Should I take on the extra project?
Should I set a boundary about my hours this week?
Should I mentor someone on my team?
Should I learn a new skill this month?

Food & Lifestyle

These are the lowest-stakes questions on the list, and that is exactly the point. Food and lifestyle decisions eat up a surprising amount of daily mental energy precisely because they do not matter enough to deserve it. Handing them to a 50/50 button frees up that energy for decisions that do matter.

Should I order pizza tonight?
Is it time for a snack?
Should I go to the gym?
Should I try the new restaurant?
Is it worth cooking tonight?
Should I have dessert?
Should I start a diet today?
Should I drink more water?
Is it too late for coffee?
Should I meal prep this week?
Should I try that recipe I bookmarked?
Should I skip the gym and go for a walk instead?
Should I finally clean out the fridge?
Should I treat myself today?
Should I cook for the whole week on Sunday?
Should I try a new coffee order?
Should I skip the snooze button today?

Travel & Adventure

Travel decisions often come with a deadline (a booking window, a limited-time fare) that makes overthinking especially costly. A quick random check can be a useful way to notice whether you are hesitating out of genuine uncertainty or just travel anxiety.

Should I book the trip?
Should I take the scenic route?
Is today a beach day?
Should I travel solo?
Should I extend my stay?
Is this the right destination?
Should I take a staycation?
Should I try adventure sports?
Is it time for a road trip?
Should I explore a new city?
Should I book the earlier flight?
Should I splurge on the nicer hotel?
Should I pack light this time?
Should I visit somewhere I’ve already been?
Should I say yes to the spontaneous trip?
Should I try the local street food?
Should I unplug from my phone for the trip?

Games & Fun

These questions are less about decisions and more about play. They work as prompts for truth-or-dare, party games, or just passing time with friends, where the fun is in the randomness itself rather than in what the answer reveals.

Should I go first?
Is this a dare or truth?
Should I pick the mystery box?
Should I reveal my hand?
Is this a bluff?
Should I take another turn?
Should I try a new hobby?
Should I watch that movie?
Should I play that game?
Is it time for a dance break?
Should I challenge them to a rematch?
Should I pick the harder difficulty?
Should I let them win this round?
Should I try the game everyone’s talking about?
Should we start a new game night tradition?
Should I use the Yes No Button to settle the tiebreak?
Should I go for the riskier move?

Daily Decisions

The everyday, no-stakes-at-all questions that fill up a normal day. These are the questions the button was built for: not because they matter, but because they don’t, and yet they still take up space in your head until you decide them.

Should I get out of bed?
Is it too late for coffee?
Should I call them back?
Should I take a nap?
Should I go for a walk?
Should I read that book?
Should I clean today?
Should I buy that thing?
Should I wake up early tomorrow?
Should I try something new?
Should I answer emails now or later?
Should I take the stairs?
Should I start that show everyone recommended?
Should I go to bed earlier tonight?
Should I finally organize my desk?
Should I put my phone away for the evening?
Should I do the thing I’ve been putting off today?

How to Use This List

Pick a category that matches what’s on your mind, or scroll until a specific question jumps out. Type it into the question field on the Yes No Button, press the button, and notice your reaction to the result before you notice the result itself. If you want the randomness to extend to which question you ask, not just the answer, try the category picker on the homepage: it fills in a question automatically when you tap a topic, and works well as a quick decision-making game with friends or as a journaling prompt when you’re not sure what to write about.

Frequently Asked Questions

How many yes or no questions are on this list?

This page has over 100 categorized questions across six everyday topics, with room to combine or adapt them to your own situation. Pair any of them with the Yes No Maybe mode if a question deserves a third, more nuanced option.

Can I use these questions for journaling instead of the button?

Yes. Many people use this kind of list as a set of journal prompts rather than questions for the button itself. Pick one, write down your gut answer before you think too hard about it, then write a sentence about why. The list works the same way whether the “answer” comes from a button or from your own pen.

Are these questions appropriate for kids?

Most of the daily decisions and games categories work well for younger audiences. For a version built specifically with families and kids in mind, see the Kids Yes No Button, which has its own set of simple, playful questions.

Do I have to use the exact wording from this list?

No. These are starting points. The best yes or no question is the specific one that’s actually on your mind, phrased in your own words. Use this list to see the pattern, then write your own version if none of these quite fit.

Do these questions come with answers?

No, and that’s on purpose. This isn’t a quiz with a fixed answer key: it’s a list of prompts you feed into a random 50/50 result. The “answer” is whatever the button lands on, and the more useful signal is your own gut reaction to that result. If you’re looking for grammar-style yes/no question examples with model answers instead, that’s a different kind of resource than what this page provides.