[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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Ultimate Life and Values Dilemmas (21–30)
If you were to be reborn, which would you choose: a dog in a wealthy household or a stray cat that can live freely?
This question asks you to imagine being reborn as an animal and consider what kind of environment you’d want to live in.
Would you choose a comfortable life as a dog in a wealthy household, or live freely as a stray cat in the wide world? The key decision points are whether you prefer the limited world indoors or the boundless world outside, and whether you want a protected situation or one where there’s risk to your life.
It’s not about whether you like dogs or cats; what matters is using each environment to expand your vision of an ideal way of living.
Two-choice questions about work, relationships, and romance (1–10)
When it comes to dates, are you the type to plan them out or go with the flow?
If you were going on a date with someone of the opposite sex, would you plan it out or just go with the flow? That’s a pretty tough question, isn’t it? Planning a date with someone you like can be exciting, but wandering around based on the mood at the time also sounds fun.
Which would you choose? It might be interesting to shift perspectives—like thinking about what you would do, or which you’d prefer if your date planned it for you.
If someone you like is among the group enjoying this ultimate either-or question together, you’re probably especially curious about their answer.
Which would you choose as your boss? A boss with a good personality but poor job performance, or a boss with a bad personality but strong job performance?
When you’re working at a company, you probably find yourself thinking about your boss from time to time.
Would you prefer a boss who’s highly competent? Or one who may not be as capable but has a great personality? Your answer might depend on what you value most in your work.
That said, thinking “both matter” is also perfectly valid.
The things that truly matter are often contradictory.
Having your own core principles and considering things from the other person’s perspective are both essential in life.
Even though these ideas can seem at odds, what’s important is aiming for a balanced middle ground.
So try to approach this either-or question with a lighter heart.
Which would you date: someone who likes the same things as you, or someone who dislikes the same things as you?
The ultimate either-or question, “Date someone who likes the same things as you, or someone who dislikes the same things as you?” might be important not only in love and as a deciding factor for marriage, but perhaps even in friendships.
If you share hobbies and other likes, the time you spend together is fun.
But if your partner likes something you dislike, it inevitably turns into a choice between putting up with it or getting into arguments.
If you love the person enough that you’re willing to tolerate it, that can be its own kind of happiness—but try to imagine how things will be in the long run and think it through.
Which would you choose: being loved forever by someone you don’t like, or never being rewarded by someone you do like for your whole life?
The ultimate either-or choice of “being loved forever by someone you don’t love” or “never being rewarded by the one you do love” has long been a classic in love stories across generations.
There are even famous sayings like “The longest-lasting love is unrequited love” and “The only love that endures is one-sided,” so at first glance the latter may seem more beautiful.
However, if you consider that the “someone you don’t love” in the former is the position you occupy in the latter, doesn’t the perspective shift? It’s ultimately an extreme hypothetical meant to be answered on instinct for fun, but why not use it as an opportunity to think about what happiness means to you, in case you ever truly face such a situation?
Which would you choose: no smartphones for life or no talking to people for life?
The ultimate either-or question of “No smartphones for life or no conversations with people for life” is likely one whose answers vary greatly depending on the era and generation.
If you communicate in writing on a smartphone, you can still get your point across, and you might be able to maintain connections with others without going out of your way to converse.
On the other hand, written exchanges make it hard to see emotions and can easily lead to misunderstandings, and without actual conversation, true mutual understanding is difficult.
It’s an ultimate either-or that perfectly evokes a modern context.
Does friendship between men and women exist or not?
This is a question that asks whether it’s possible to maintain a friendship between men and women, or whether it inevitably develops into other feelings.
It lets you sense how a person approaches the opposite sex and also provides a chance to learn about their tendencies in friendships.
If you have personal experiences or stories you’ve seen or heard for each pattern, the conversation is likely to get even more lively.
It’s a topic that’s especially enjoyable when people with different viewpoints are present, since you can exchange opinions and have fun with the differences.