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

Social worker / Care workermoko
My name is Moko, a mother of three who admired my mother and worked in the care industry as a care worker and as a medical social worker (MSW) in a hospital. I will be drawing on my previous experience to write mainly about caregiving. Thank you in advance.

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.

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

Which one would you rather have as your boss?

A boss who is nice but incompetent at work
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.

Raise the rankinglower

Nakajima Junko

Report a problem

In conclusion

“Which do you prefer?” questions are simple yet surprisingly lively, making them great allies for sparking conversation. Precisely because there’s no right answer, you get a glimpse of each person’s values and tastes, which can lead to unexpected common ground and new discoveries. Why not enjoy a time where the conversation expands and smiles abound?