Riddles Gone Wrong

JJ Lamb
4 min readJul 1, 2019

One of my favorite activities as a middle school teacher during days when instruction isn’t really an option is to give my class riddles. It’s a fun way to make sure the gears are turning in their heads without overtaxing them on days when they have to take standardized tests or its late June and the school year is basically over. 99% of the riddles go smoothly, kids give their best guess, some of them are right. The other 1% doesn’t go exactly as planned.

A Bleak Outlook

A couple of weeks ago, I was wrapping up my fifth year as a teacher and we only had three days until the end of the year. Our final project was done, everything was turned in and graded and the last two days of school were going to be a celebration of the school year with social-emotional activities. It was the perfect time for riddles. I split the class up into teams of four with a mini-whiteboard and a dry-erase marker. Every time they guessed the correct answer, the team got a point. About halfway through the period, I gave them the riddle “what has forests but no trees, rivers but no water and cities but no people?”

The first round of guesses from every team were incorrect. The popular guess was “a picture,” which is sadly wrong. So gave the teams a chance to guess again for two points instead of one.

That was my mistake.

I have one student, admittedly she was one of my favorites throughout the year, who has found her comedic style to be rather dark and edgy. (1) While the rest of her group was stumped with this riddle, she took over and made her best guess. (2)

When the groups raised their boards to show their guesses, she wrote the answer “our future.”

The collective “oh my God, Jill” (3) was palpable.

Maps. The answer was maps.

The Psychopath Test

There is a riddle out there commonly referred to as the psychopath test: “While at her own mother’s funeral, a woman meets a guy she doesn’t know. She thinks this guy is amazing — her dream man — and is pretty sure he could be the love of her life. However, she never asked for his name or number and afterwards could not find anyone who knows who he was. A few days later the girl kills her own sister — but why?”

The general thesis is that if you can answer this question correctly without putting too much thought into it, there is a decent chance that you are a psychopath. A couple of years ago, I was teaching at a different school in a position that gave me smaller class sizes.

During standardized testing, it was frowned upon to do rigorous work with the students, so we were encouraged to find engaging activities that were not just watching a movie.

Enter riddles. I had a giant bag of Starbursts and the first student to raise their hand and guess the correct answer would get one. (4)

Eventually, I gave them the psychopath test. To have a little fun, I told them if they got it correct quickly then they might be a psychopath. This got them excited to get the correct answer because having a cool reputation is everything in middle school.

They were tripping over themselves only to get the wrong answer time after time. Kids kept repeating the same guess “her sister was dating to him” again and again as if saying it a third time would make it correct. It didn’t. After a couple of minutes, students were ready to give up and move on to the next riddle. Just then, a girl returned from the bathroom and asked what the riddle was. I told her without the preface of it being commonly referred to as the psychopath test.

She said, “so the man would come to the funeral” without giving it a second thought.

She claimed her Starburst.

Bonus: The only riddles my students have never been able to guess is “how do you fit nine cows in eight boxes?” and “how far can a dog run into the woods?” Comment your guesses below.

Every penny from my writing goes to supporting my fiance pay off her student loans. Please read, clap and follow for more posts on teaching, reading, and basketball. Follow on Twitter: @kuujamzs

1: During our poetry unit, when I said that poems should pack an emotional punch, she raised her hand and asked: “what if I don’t have emotions?” So that’s who we are dealing with here.

2: It was not her best guess.

3: For the record, I will never use my students’ real names. For consistency purposes, all of my students will be named Jack and Jill. (3a)

3a: I don’t know what will happen if I ever teach a student named Jack or Jill.

4: Otherwise the yelling and screaming would have been migraine-inducing.

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JJ Lamb

Midwest teacher by day, exhausted and asleep by night. Teaching, Reading, Writing, Basketball.