With friends or couples! A set of questions perfect for penalty games

Keyboard playerSAKI
I’ve been playing the Electone since I was six, mainly performing Disney music, anime songs, and music from dramas and films. I post performance videos on YouTube and social media, and I also give concerts. Building on my Electone experience, I took up synthesizer and piano during my student years and performed at school-sponsored events. As a writer, I’ve covered not only music-related topics but a wide range of genres, so I hope to draw on my experience to deliver articles that make readers think, “I want to try that!” or “I want to listen to that!”
A Vocaloid producer who is also a music writerAraki Jakkan
I’ve worked in a variety of roles—regardless of pro or amateur settings—including live event PA, cameraman for video and photography, restaurant staff, and logistics center staff. I now spend my days as a part-time writer. I’ve contributed to music and manga websites with feature/review articles, and wrote the liner notes included as a bonus for 1st PLACE Inc.’s “IA SUPER BEST.” As for my music background, I started playing guitar in junior high and focused on band activities during my school years. For over 15 years since then, up to the present, I’ve continued releasing original tracks as a Vocaloid producer. My areas of expertise are Japanese rock, Vocaloid, and manga.

When was your first love? What’s your ideal date? Questions like these make anyone blush, right? But they’re actually perfect for penalty games! Not only can you discover an unexpected side of someone, you also get to enjoy their embarrassed reactions.

In this article, we’ll introduce great romance-related questions that are sure to liven up the mood.

They’re perfect for parties or casual hangouts with friends—questions that will make hearts flutter and everyone laugh! Be sure to include them in your next game’s penalty!

Past and memory-themed punishment game questions (11–20)

What do you regret from your school days?

The forfeit question, “What do you regret from your school days?” is a classic conversation piece where laughter and empathy intersect.

Try answering seriously and it feels embarrassing; joke around and it oddly gains depth—that’s the charm of this prompt.

“My first love ended without a confession,” “I pushed the dress code so far it became a black mark,” “I bombed at the school festival”—that perfect blend of cringe and humor warms up the room fast.

The more memorable the failure, the easier it is to get playful jabs and keep the topic rolling.

Everyone’s got at least one slightly uncool past moment—why not turn it into a bit, share a good laugh, and relive those nostalgic times together?

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kojifumi

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What real-life story will absolutely make you laugh if you hear it?

It’s a question that sets a pretty high bar for the person answering, since they absolutely have to make the other person laugh.

For people who usually live smartly and keep it cool, it’ll probably feel like a tough penalty game to answer! You might even get to hear real-life stories you’d never imagine from them normally.

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miyabi

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What is the minimum score on the test?

Do you remember the lowest score you ever got on a test? If this feels like a punishment game to you, a specific answer sheet you’d rather forget probably came to mind.

It’s an even better conversation starter if you share the subject and the story behind why you ended up with that score.

Admitting your lowest score can be a little embarrassing, but by telling an awkward story, you might spark lots of questions and end up feeling much closer to friends or a partner!

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sasashina

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What’s a mistake you made recently?

This is a question I especially recommend for working adults.

Everyone makes mistakes.

I don’t mean to make fun of anyone, but it’s also true that when you hear about them from others, you can’t help but laugh.

And as I mentioned above, stories about the unbelievably silly mistakes you made as a working adult really get the conversation going.

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Araki Jakkan

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What would you like to say to yourself from 10 years ago?

This question is so tough that it wouldn’t be an exaggeration to call it an unreasonable ask! The other person will first be baffled, thinking, “What was I doing ten years ago?” If it’s between longtime friends, it could even turn into a fun punishment-game topic that gets everyone reminiscing.

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miyabi

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What was the most embarrassing event in your life?

Let’s go with a straight-to-the-point question.

Share, openly and honestly, the most embarrassing moment of your life that you’ve been keeping secret! It should create that perfect “this is a punishment game” vibe.

It might also be fun to have them reenact it with gestures and body language!

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Araki Jakkan

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