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

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/Memories Punishment Game Questions (1–10)

How does your family address you? What do they call you?

How does your family address you? What do they call you?

For some people, this question basically turns into a punishment game! If you’re usually called by your name without any honorifics, it’s no big deal.

But if you’ve always been addressed with “-chan” or “-kun” since you were little, or you go by a quirky nickname, it might be a pretty embarrassing dare.

It’s probably especially unpleasant for men, maybe? Depending on the person, this dare can get everyone really hyped, but keep the fun and any talk about names limited to that moment.

Imitating or teasing someone about it after the game is over is a no-go.

What is your earliest memory?

What is your earliest memory?

The dare question “What’s your earliest memory?” turns out to be a surprisingly deep, crowd-pleasing prompt.

When you spring it on people, you’ll hear a flurry of stories that blend impact and embarrassment—like “I crashed my tricycle into a utility pole” or “I wet myself at daycare and bawled.” The fuzziness of early memories makes it easy for tales to get a little embellished—that’s part of the fun.

People even surprise themselves mid-story with lines like, “Wait, did I really do that?” and the laughs just keep coming.

This question brings out a person’s unique vibe and can transform simple reminiscences into hilarious talk.

It’s a warmly bonding, highly recommended dare topic.

What’s a gift you’ve received that was kind of underwhelming?

What’s a gift you’ve received that was kind of underwhelming?

Not only on special occasions like birthdays and Christmas, but also at random moments, you may receive gifts.

This piece is about looking back on those gifts you received that, if we’re honest, felt a bit underwhelming.

Think carefully about the stories behind those presents—did you feel it was lackluster the moment you got it, or did it only seem so after you tried using it? Keep in mind that recalling these memories might not only affect the recipient but could also hurt the feelings of the giver, so a bit of sensitivity may be necessary.

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

What’s something you bought before that turned out to be a mistake?

What's something you bought before that turned out to be a mistake?

In everyday life, we shop with all kinds of intentions—checking out the latest items, or searching for something that suits us.

This piece invites people to look back on purchases they feel were failures, drawn from that everyday habit of shopping.

There might be cases where trying to save money backfired, or where something expensive still turned out to be disappointing—plenty of different episodes are likely to come up.

Let’s listen to these stories while paying attention to whether the failure is unique to that person or something many can relate to.

What’s the most expensive thing you’ve ever bought?

What's the most expensive thing you've ever bought?

From the essentials of daily life to hobby-related items, you’ve probably purchased a wide range of things—some of them quite expensive.

This activity asks you to look back and recall what your most costly purchases have been.

It’s recommended to reflect carefully, including the feelings and intentions you had when you decided to buy those expensive items.

You might even uncover a sad story about an expensive purchase that, in hindsight, felt like a mistake.

What hasn’t changed since you were a child?

What hasn’t changed since you were a child?

The question “What hasn’t changed about you since you were a kid?” is perfect for punishment games—it’s prime material that brings out a person’s true self.

When someone recalls and talks about the innocent traits or quirks they’ve kept, the room fills with laughter and a sense of closeness.

For example, saying “I still sleep with a stuffed animal every night” instantly makes you the center of attention thanks to the cute-and-embarrassing contrast.

The more striking the story, the easier it is to hype things up and keep the conversation flowing.

Watching someone share while blushing is hilarious in itself, and you can bet everyone’s witty comebacks won’t stop.

It might be a little embarrassing, but it’s a guaranteed laugh.

What strange school rules did you have when you were a student?

What strange school rules did you have when you were a student?

Depending on the kinds of people who gather there, the atmosphere of a place naturally changes—some of you may even remember your school having a distinctive vibe.

Focusing on life at such schools, this piece looks back to see whether there were any strange rules hidden in the school regulations.

Some rules may have made your school life difficult, while others were officially written yet casually ignored.

It seems we’ll uncover many different kinds of school rules.

There may even be rules that were created long ago and then left as-is, which could become a chance to feel the school’s history.