How a beloved word search game helps me teach my kids about writing (and mistakes)

Boggle is one of our favorite family games.

Growing up as an only child, I surrounded myself with words. I spent much of my free time reading, writing, and playing Boggle — a word search game. I loved shaking the plastic container of letters and seeing where they landed. There was something freeing about the idea of letters and words falling into place with the simple shake of a hand.

I would turn the hourglass timer, then silently search for words. I’d write them down on a scrap piece of paper, bringing them out of hiding. Sometimes I played by myself. Other times, with my father.

Now, I play the game with my two young children, who are 7 and 8. We use the same Boggle game I had as a kid — the 25th anniversary edition from 1997. Playing Boggle with them pleases both the inner child and the working mother in me. (During time-crunched evenings, a two-minute word search game seems far more manageable than an hour-long game of Life or Monopoly.) Playing Boggle has also been a way for me to teach my kids about vocabulary, spelling, homonyms, and homophones.

A recent game of Boggle in the Tarpley household.

During a round of Boggle the other night, I began reading off the words I had found: pie, die, pity …

“What does pity mean?” my daughter asked.

“To feel bad about someone else’s suffering,” I said.

“he, she, shave, woe, to, too …” I continued, pointing to the words as I read them.

“But mom, ‘to’ doesn’t have two O’s!” my son observed.

“Does too!” I said, chuckling at myself for the quick comeback.

I proceeded to teach him and my daughter about the differences between to, two and too, and the meaning of homophones (words that sound the same but have different spellings) and homonyms (words that have the same spelling or pronunciation but different meanings). (Sometimes I still have to remind myself of these words’ definitions so that I don’t confuse them!)

“Two and too are homophones,” I explained, “because they are spelled different but sound the same. But a dog’s bark and a tree’s bark are homonyms because they’re spelled the same but have different meanings.”

I’m not sure if the lesson stuck, but I nevertheless liked introducing my kids to these concepts. I also shared a story with them — about one of the first articles I ever wrote for The Poynter Institute, where I started working straight out of college. It was 2007, when Twitter (now X) was first starting to emerge. I was interested in exploring how journalists could use Twitter as a reporting and writing tool, so I wrote a two-part series about it for Poynter’s website. (This was back when The New York Times had 400 followers; it now has more than 55 million.)

The story got a lot of positive attention and was even mentioned in The New York Times. But it also had an error. When describing the caret symbol (^), I incorrectly spelled the word as “carrot.” A reader called me out on it in the comments section and another emailed me about it. As a young journalist who wanted to make a good impression in my first job out of college, I was mortified. At the time, I confided in my colleague and mentor, Roy Peter Clark, who decided to turn the mistake into a learning opportunity.

As a writing coach, he said we could use the mistake to help other writers be more attuned to pesky homophones. Not long after, he wrote a story about what happened. It began:

I bear some responsibility for a mistake that appeared in a column by my colleague and editor, Mallary Jean Tenore. In her informative piece on Twitter, she wrote “carrot” for “caret.” A couple of readers took the stick to her and Poynter for not making the catch. Mea culpa. I didn’t see it when reading a draft of the piece, and could not have distinguished a “caret” (^) from a mathematical “less than” sign (<) — which looks like a prostrate caret to me. (Or is it “prostate”?)

After the story ran, Roy gifted me a decorative carrot as a comical reminder that mistakes happen. (Eighteen years later, I still have the carrot!)

I still keep the carrot in a my home office. My cat got ahold of it years ago, so I have to keep it tucked away in a drawer…

I have never misused the words carrot, carat, and caret since then, just like I never misused the homonyms principle and principal after my grandmother once told me: “Just remember, the principal is your pal.” But I still sometimes catch myself making homonym- and homophone-related mistakes — a reality that I shared with my children during our Boggle game.

“Mommy still makes mistakes,” I told them. “All writers do. But good editors can help.”

I told them about how, in my most recent freelance story, I mistakingly wrote stationary (with an A) instead of stationery (with an E). (Stationary means not moving; stationery is the paper you write on.) As a lifelong stationery lover, I was surprised that I had dropped the ball on this spelling but grateful my editor caught it prior to publication.

Sensing that my kids were done with my lesson, I suggested we start another round of Boggle. As we searched for words, I thought about how the game not only reminds me of my childhood but of my ongoing quest as a writer — to find the right words, to always search for meaning.

I’d love to hear from you! Any other Boggle fans here? (Or Scrabble, or Wordle?) What homonyms or homophones tend to confuse you as a writer?