[Ultimate Either-Or] A great conversation starter and a chance to get to know each other!
Have you heard of the ultimate either-or questions? They’re two-choice questions where it’s hard to pick one, but you have to choose, and they can reveal a person’s values and spark conversation.
They’re perfect as conversation starters with friends or partners and for getting to know each other.
In this article, I’ll introduce a collection of ultimate either-or questions related to life and personal values.
There are plenty of prompts that will make you agonize over which to choose, so have fun giving them a try!
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Two-choice questions about work, relationships, and romance (1–10)
Would you rather be with someone who talks all the time or someone who doesn’t talk at all?
When faced with the ultimate either-or question—“Would you rather be with someone who talks nonstop or someone who doesn’t talk at all?”—if you truly had to pick one, you’d probably decide based on your own personality and preferences.
In the former case, if you’re a talkative type, the conversation would be lively but you might not get to fully share your own stories; if you’re not talkative, they would keep the conversation going and take the lead.
In the latter case, if you’re a talkative type, you could talk as much as you want but get no response and feel little engagement; if you’re not talkative, nothing would really happen even if you’re together.
Since both options have pros and cons, it really is the ultimate either-or choice.
For the date, do you prefer outdoors or indoors?
This is a question that asks someone to think about which setting is ideal for a date: indoors or outdoors.
Each has its own appeal—outdoors offers a sense of freedom, while indoors isn’t affected by the weather—and their answer can reveal which they prioritize.
Beyond simply asking indoors or outdoors, expanding the topic into a concrete ideal plan can also make the conversation more engaging.
It’s also recommended to have them consider not only the advantages of each option but what kinds of problems might arise.
That way, you can get a sense of how they handle unexpected situations.
Which one is more accepted: being bad at sports or having a poor sense of direction?
This is a question that asks you to consider which of two negative traits would be more acceptable: being clumsy at physical activities (unable to perform movements as smoothly as you’d like) or being bad with directions (unable to grasp the direction of your destination well).
Imagine concrete situations in daily life where you might have these traits and think about which would cause you more trouble.
If you’re asking someone who already has one of these tendencies, have them imagine that trait becoming more extreme; that way, it turns into an ultimate question.
Which would you dislike more? Which one could you somehow overcome? Let’s consider which to choose from various angles.
If you could only choose one kind of boss: one who’s always watching you, or one who never pays attention to you?
If you could only choose one kind of boss—one who constantly monitors you or one who doesn’t watch you at all—it’s a tough either-or that also depends on the level of trust already established.
For new employees who haven’t learned the job yet, some oversight is necessary, but nowadays that can easily be perceived as pressure.
On the other hand, with a boss who doesn’t check in at all, the work might feel easygoing and allow you to proceed at your own pace, but for the workplace it poses a major risk: mistakes often won’t be discovered until problems actually arise.
It’s an extreme choice, and the “right” answer will vary widely depending on personality and generation.
Two choices for work, relationships, and romance (11–20)
If you have a fight, which are you: absolutely unwilling to apologize, or the one who apologizes first?
In relationships with others, sometimes arguments happen, don’t they? This question asks whether, when such a quarrel occurs, you would apologize first or not.
It can reveal how strongly someone sticks to their beliefs and the intensity of their feelings.
The answer may vary depending on what the argument was about or who it was with, so it’s also a good idea to imagine different scenarios and use them to explore the person’s stance and personality.
Which would you dislike more: a husband or wife who doesn’t do any housework at all, or a husband or wife who constantly interferes and comments on the housework?
This question asks, within the context of a relationship with a husband or wife, what kind of involvement in housework you dislike.
Consider which you find worse: a partner who does nothing at all, or one who interferes and comments on how it should be done.
Some people may even know the worst-case scenario that combines both—someone who doesn’t help yet still criticizes.
It’s a question that can also reveal differences in how difficult each person finds housework and how they want to approach it.
Which would you rather protect when a disaster strikes: your family or yourself?
This is a question that asks, if you were faced with a disaster, whether you would prioritize protecting your family or yourself.
Saying you would protect your family may sound more admirable, but there’s also the view that in order to properly protect your family, you should first protect yourself.
How you protect each one may differ, and the methods could vary depending on the type of disaster, so specifying the situation in detail might lead to more concrete answers.
It’s perfect not only for checking a person’s priorities, but also as a conversation starter to see how concretely they’ve thought about a what-if scenario.



