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[The Ultimate Either-Or] Which Side Are You On? A Surefire List of Either-Or Questions to Liven Things Up

Have you ever run out of things to talk about during a drinking party or a get-together with friends when there’s a little downtime? That’s exactly when “Which side are you on?” either-or questions come in handy.

They’re simple, yet once you hear someone’s answer, you can’t help but ask why—conversation naturally opens up with a kind of mysterious charm.

You might be surprised by differences in preferences, or get excited discovering unexpected common ground.

In this article, we’ll introduce “Which side are you on?” prompts that can instantly warm up the vibe.

From classics like “Dog person or cat person?” and “Takenoko no Sato or Kinoko no Yama?” these are sure to energize any group.

Enjoy a fun time while discovering unexpected sides of the people you’re with.

[Ultimate Either-Or] Which side are you? A guaranteed-to-excite collection of either-or questions (1–10)

Which snack do you like better?

Which snack do you like better?
  1. Bamboo Shoot Village
  2. Kinoko no Yama

An age-old, ultimate either-or topic among people who love sweets. Takenoko no Sato features crumbly cookie dough loaded with chocolate. Its balance of sweetness and satisfaction is spot-on, and many say it “feels like a proper treat.” On the other hand, Kinoko no Yama has a light cracker topped with a neat dollop of chocolate, offering a crisp bite that’s its biggest draw. It’s so easy to eat that you can’t help reaching for “just one more.” Because both are equally beloved, this debate only gets more passionate the more you talk. It’s a foolproof conversation starter that can range from light chit-chat to deep dives into personal preferences.

Which one is necessary for love?

Which one is necessary for love?
  1. love
  2. gold

A question that makes your heart skip a beat: the ultimate either-or. We all know both matter, but if you force yourself to choose one, your values start to reveal themselves. Those who choose “love” are the type who treasure the comfort of mutual understanding and the time spent laughing together above all else. Even when things get tough, they may be drawn to a relationship where the two of you can overcome challenges together. On the other hand, those who choose “money” tend to be practical and steady. With a stable life comes peace of mind and an easier time planning for the future—and that way of thinking is perfectly valid. There’s no right answer; both are important. Let this question be a springboard to talk about what you truly seek in a relationship.

Which one do you want to go to?

Which one do you want to go to?
  1. past
  2. future

If you had a time machine, where would you like to go? If you choose the past, many people might do so because they want to redo certain events or meet someone dear to them once more. On the other hand, the future is a world no one has seen yet. There’s an alluring mix of excitement and a little nervousness—wondering what you’ll be like and how society will have progressed—that makes you want to take a peek. The interesting part is that your choice reveals how you see the present and what you’re hoping for. It’s a classic either-or question that’s easy to get people talking and quickly broadens the conversation.

[The Ultimate Either-Or] Which Side Are You On? A Surefire List of Either-Or Questions (11–20)

Which would you choose?

Which would you choose?
  1. A guaranteed 1,000,000 yen
  2. 10 million yen that you can receive with a 50% chance

The moment you’re asked, your personality shows—this is the ultimate either-or question. Those who choose “a guaranteed 1 million yen” are safety-first types. The peace of mind from a solid gain is powerful, and the fact there’s no risk of ending up with zero is a major draw. On the other hand, those who choose “a 50% chance at 10 million yen” are challengers betting on dreams and romance. Since it’s an amount that could change your life in an instant if you win, the thrill is on a whole different level. Even if the expected value is roughly the same when you think calmly, the answer splits depending on emotional sway and personal values—that’s what makes this question interesting. Are you a gambler or a steady type? It’s a classic, crowd-pleasing either-or that smoothly leads into a friendly personality talk.

If you could get a special ability, which would you choose?

If you could get a special ability, which would you choose?
  1. The ability to read future events
  2. the ability to read people's minds

The ability to read future events is appealing for the peace of mind that comes from knowing what will happen in advance. It might help you avoid failure and seize opportunities more easily, but there’s also the fear of knowing too much. The ability to read people’s minds could reduce misunderstandings in relationships by revealing what others truly think. However, you might also learn things you’d rather not hear. Do you choose peace of mind, or deeper connection? Which would you pick? It’s a short but engaging either-or question that clearly divides values.

Which one would you rather have as your boss?

Which one would you rather have as your boss?
  1. A boss who is nice but incompetent at work
  2. A boss who has a bad personality but gets the job done

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 choose for a trip?

Which would you choose for a trip?
  1. Hokkaido
  2. Okinawa

Japan is full of wonderful tourist attractions. Among them, Hokkaido and Okinawa are arguably some of the most popular destinations. Hokkaido offers many local specialties and natural wonders that take advantage of its climate and vast landscape, including fresh seafood and places like Lake Akan and Shikotsu-Toya National Park. Okinawa, too, has activities and specialties unique to its warm climate. Snorkeling, diving, soki soba, and sea grapes are especially famous. Moreover, both regions have fascinating histories and cultures, and experiencing them is one of the great pleasures of visiting. The more you learn about Hokkaido and Okinawa, the harder it is to choose between them.