60 Grown-Up This-or-That Questions That Reveal More Than You'd Think

"Mountains or beach?" "Bad news first or good news first?" On the surface, this-or-that questions look like filler for an awkward silence — a small game where the answer barely matters, since nothing changes either way. But if you've ever watched a group of friends start actually arguing over one of these, sometimes getting genuinely worked up about it, you'll notice something: these questions aren't boring at all. The interesting part was never the options themselves — it's the "why" that comes right after.

This article is about turning this-or-that from a fill-in-the-blank party game into a doorway to seeing who someone really is.

Why either-or opens conversation better than open-ended questions do

Open questions like "what's your philosophy on life" sound deep, but thrown out cold, people often freeze — they don't know where to start, and the moment gets awkward. This-or-that does the opposite: the options have already narrowed the field to two, so the bar to answer drops to almost nothing. Nearly everyone can blurt out something instantly.

But a low bar doesn't mean shallow content. The real information is hiding in why someone chose what they chose. Someone who picks "bad news first" might have grown up in a household that always hid problems, so sitting with unspoken bad news makes them anxious. Someone who picks "good news first" might just believe that easing into a mood makes the bad part easier to face. Same answer, completely different reason — and the reason is the part that's actually telling you who this person is.

That's exactly why this-or-that works so well for getting to know someone new, or for learning more about someone you've known forever but rarely talk deeply with. It gives both people a low-pressure entry point that doesn't demand vulnerability right away — but the moment you're willing to ask "why," the conversation naturally moves somewhere deeper.

"Why" is the real question — the options are just the door

This is the single most important thing to remember when using this-or-that: the options themselves were never the point. They're bait — something low-stakes enough that people are willing to speak up. What's actually worth asking, and worth listening to, is always the next line: "why did you pick that?"

Here's an example. Ask someone: "a stable but boring job, or an unstable but passion-driven one?" Hearing just "stable" or "passion" only tells you the outcome, not the reason. But follow up with "why?" and you might hear something like:

• "My parents' business failed when I was a kid, and money fights tore our house apart for years — I've been sensitive to 'unstable' ever since." That's a story about family history and financial security.
• "I once quit a job chasing passion and realized what I thought was passion faded in three months. Now I trust more that fulfillment shows up if you stick with stability long enough." That's a story about a shift in self-understanding.

Same answer — "stable" — but two completely different inner maps. Without the "why," you'd assume these two people were the same kind of person.

So next time you play this-or-that, treat it as an opening line, not the answer itself. The options open the door — "why" is the part you actually came for.

60 grown-up this-or-that questions, by category

Here are 60 questions across four categories — lifestyle, values, relationships, and fun — chosen to avoid anything where either answer genuinely doesn't matter. Look for the ones that make someone pause, or that they can't resist explaining once they've answered.

Lifestyle

1. Live your whole life in a city, or in the countryside?
2. Early to bed and early to rise, or a night owl through and through?
3. One long vacation a year, or a short trip every month?
4. Minimalist living, or an unrepentant collector?
5. Cook at home, or eat out most of the time?
6. Own a home with a mortgage weighing on you, or rent stress-free?
7. Live alone, or always have a roommate or family around?
8. Phone glued to your hand, or could go a full day without checking it?
9. Every day scheduled solid, or lots of unplanned white space?
10. Save toward a house, or spend on experiences and travel?
11. Drive everywhere, or take public transit?
12. Sleep in on weekends, or get up early to stretch the day out?
13. Dog person or cat person?
14. A home that's always tidy, or one that's a bit messy but feels lived-in?
15. A stable job, or unpredictable income from freelancing?

Values

1. Honest even if it hurts, or kind even if it means hiding part of the truth?
2. Bad news first, or good news first?
3. Upset people to stick to a principle, or look the other way to keep the peace?
4. A fair process with a mediocre outcome, or a great outcome with a slightly gray process?
5. Busy but meaningful, or easy but a little boring?
6. Disliked but fully yourself, or liked but bending yourself a bit?
7. Earn more but rarely see family, or earn average but home for dinner every night?
8. Believe people are basically good, or better safe than sorry?
9. Admit a mistake honestly and get scolded, or bury it and carry a quiet unease?
10. A life that follows the plan completely, or one that improvises as it goes?
11. A stable but boring job, or an unstable but passion-driven one?
12. Do the right thing and feel alone in it, or go along with everyone and feel uneasy?
13. Follow the rules and lose out, or bend them a little and feel a bit off about it?
14. Reputation matters more, or peace of mind matters more?
15. Say an uncomfortable truth, or a comfortable half-truth everyone's fine with?

Relationships

1. Hash it out with your partner the moment you disagree, or cool off first, then talk?
2. Lots of friends but not deep ones, or few friends but very deep ones?
3. Make decisions together with a partner, or each keep some space of your own?
4. Family always comes first, or your own life comes first?
5. Is the one who apologizes first in a fight more mature, or the one who cools down first?
6. Say "I love you" first, or wait for the other person to say it first?
7. Stay out of it when friends fight, or always weigh in and help sort it out?
8. When you disagree with a partner, do you compromise, or hold your ground?
9. Stay friends after a breakup, or a clean, total break is healthier?
10. Give more slack to family than friends, or the other way around?
11. Is love "wanting to give the other person the best," or "wanting to grow better together"?
12. Long distance but stable, or seeing each other often but fighting often?
13. Lend a friend money if they ask, or believe money and friendship shouldn't mix?
14. Rearrange your plans for a friend, or believe taking care of yourself comes first?
15. In relationships, are you more afraid of losing the other person, or losing yourself?

Fun

1. A big group party, or a small hangout with three or four close friends?
2. Movies or TV series?
3. Mountains or beach?
4. Theme park or nature trail?
5. A concert or a music festival?
6. Board game night, or bar-hopping till late?
7. Travel alone, or always with company?
8. A meticulously planned trip, or a spontaneous, wherever-the-wind-takes-you trip?
9. Rewatch an old favorite, or always pick something new?
10. Lie around at home doing nothing all day, or go out and find something to do?
11. Karaoke or an escape room?
12. An afternoon parked at a café, or an outdoor activity that works up a sweat?
13. Binge a whole series overnight, or savor one episode a day?
14. A surprise party for your birthday, or a quiet one, just for yourself?
15. Late-night deep talks, or easier conversation in the daylight?

How to actually use this: dates, road trips, group hangouts

A list of questions alone isn't enough — how you play it is what makes it work.

On a date: Don't lead with heavy values questions right out of the gate. Warm up with lifestyle or fun questions first, then let the conversation drift toward relationships or values once things feel more relaxed. And always remember — after the other person answers, follow with "why?" before moving on to the next question. The failure mode on a date isn't running out of topics — it's staying on the surface, cycling through questions without ever going deep on one. Five questions each pushed all the way down beats twenty shallow ones.

Road trips: A car is one of the best settings for this-or-that, because everyone's facing forward instead of making eye contact — which, similar to why counseling sessions sometimes work better side-by-side than face-to-face, actually makes it easier to say something real. On a long drive, take turns asking, answer, then follow up on each other's reasons. It's a great way to fill three or four hours in the car — and you'll walk away knowing the person next to you far better than the radio ever would have let you.

Group hangouts (3+ people): Try the "guess first, then reveal" variant — everyone guesses what a specific person will pick, then that person reveals their answer and explains why. This is especially good at energizing a room, because getting the guess wrong usually gets a laugh or a "wait, that's not who I thought you were!" — and the act of guessing itself often surfaces observations people wouldn't normally say out loud, like "I always figured you were more of a ___ person."

One rule holds regardless of the setting: when someone gives an answer that surprises you, resist the urge to argue or correct them. Ask "what made you think that?" instead — that one second of genuine curiosity usually does more than the next ten sentences to keep them talking.

A note for anyone who doesn't know how to start a conversation

If you've never been great at small talk, or you feel weird about "just asking random questions," this-or-that is actually one of the safest openers there is. It looks light, it doesn't demand vulnerability up front — but as long as you're willing to ask "why" once, the conversation naturally goes somewhere much deeper than the surface. You don't need a clever opening line, and you don't need to be a great conversationalist. You just need to pick a question, ask it, and actually listen to the reason.

MindFlow's social card deck has a full "preference" category built around exactly these this-or-that questions, covering everything above — draw one at random and you can start talking right away. Next time you're not sure what to say, or a date or hangout hits an awkward lull, try drawing a card.