[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 choices for work, relationships, and romance (11–20)
Which would you rather work at: a job with low pay but good relationships, or a job with high pay but terrible relationships?
When choosing a job, salary and relationships with colleagues are often cited as the most important factors.
Ideally, both would be good, but this question asks which you would prioritize if you could only have one.
Some people can tolerate poor workplace relationships for a higher salary, while others would prefer to work healthily in a positive environment even if the pay is low.
It reveals each person’s approach to work.
Starting with extreme examples as a kind of ultimate question could spark a lively discussion about what balance is ideal.
In love, do you prefer to do the chasing or be chased?
This is a question that invites you to think about your ideal form of romance, revealing how each person faces love.
In a pursuit-style romance where you take the initiative, you’re tested on the ingenuity you use to win the other person’s attention.
In a being-pursued romance where you receive the other’s advances, your effort to remain their ideal is put to the test.
By looking at what kind of romantic experience someone finds fulfilling, you can sense how their emotions intensify and how they express them.
Let’s encourage even those uninterested in romance to think carefully about it, as one way to understand their way of thinking.
Would you rather work in an environment where you change departments every year, or where you do the same job for 10 years?
The ultimate either-or question—“Would you rather work in an environment where you’re transferred to a different department every year, or do the exact same job for ten years?”—depends greatly on your innate personality and what motivates you at work.
If your department or responsibilities change every year, you can gain new skills and broaden your network, but you’ll also constantly face the risk of making mistakes in unfamiliar tasks.
If you keep the same duties, your skills will improve year after year and you’ll build relationships, but you may feel stuck in a rut and find it harder to escape when trouble arises.
Both scenarios are possible depending on the workplace, but I hope this prompts you to reflect on your own personality before starting a new job.
Which would you prefer: a 10% salary increase, or keeping the same salary with a three-day weekend?
It’s the ultimate either-or question: money or time? A higher salary is great, but if the pay stays the same, a three-day weekend is hard to pass up… Which would you choose? Maybe you love your job, maybe there’s something you want to buy, or maybe you like your work but still want more free time—there are lots of reasons.
After they make their choice, be sure to ask why.
You might get an unexpected answer that completely changes the way you see them!
Which workplace would you rather work in: one where people talk behind your back, or one with power harassment?
This is a question that asks you to assume there is inevitably a problem in the workplace and consider which you find more tolerable: gossip behind your back or power harassment.
Both are unpleasant situations, but let’s carefully imagine each scenario and decide based on whether you could endure it.
Clearly picturing the “enemy,” as well as factors like the intensity of the attacks and how far they reach, will likely influence which you feel you could withstand better.
It’s also recommended to think about your answer not only from the perspective of being a one-sided victim, but also from whether you could address and handle the problem.
Which would you rather date: someone whose food preferences don’t match yours, or someone who doesn’t share your sense of humor?
People’s values vary from person to person, and precisely because of those differences, there are situations where you feel distressed when interacting with others.
This question asks you to think about which gaps you could accept if you were to be with someone whose values differ from yours.
It presents a major either-or choice between food and sense of humor, and invites you to consider what kinds of situations those differences might create.
Since both are important in life, seeing which one a person prioritizes may also reveal something about their everyday life.
Which is better for a date, sunny or cloudy?
This is a question asking someone to consider whether sunny or cloudy weather is ideal for a date.
It can also be a chance to learn what feelings they associate with each type of weather and what weather-related things they might dislike.
Since weather affects temperature, pay attention to how answers might differ depending on the season being assumed.
You might also get a sense of the person’s practical savvy—such as whether they have date plans tailored to different weather—through this question.