My Grandkids Want to Hear About My Childhood Crimes

By Allan Ripp | October 27th, 2026

Sharing childhood stories with the grandkids


Alan Ripp telling bedtime stories of his childhood mischief to his two grandkids.

“Tell us a story,” Laila and Oliver pleaded, “about when you did bad things.” Allan Ripp regularly shares stories of his childhood mischief with his grandkids – as he does here, in Boomer’s “From Our Readers.”


Vacationing with my grandkids this summer I had the cozy pleasure of tucking them into bed for two weeks straight.

After stowing their Kindles and Archie comics for the night, Laila (8) and Oliver (6) weren’t ready for me to leave.

“Tell us a story, Poppy,” they pleaded, “about when you did bad things.” Translation: instead of exotic tales of wizards or wildebeests, they preferred accounts of my semi-rogue childhood.

I wasn’t exactly a demon seed but occasionally ran afoul of parental law and did my stints in the penalty box. Like the day I threw my mom’s watch down the stairs because I wanted to see if time really flew.

“That’s nice,” she answered distractedly when I told her about my experiment. Later she found her watch in a hundred pieces at the bottom of the steps. “What did you do!” she shouted, and made me sit under her desk while she worked. Oliver and Laila can’t get enough of that one.

Or when my parents were having a dinner party and instructed me not to touch the serrated knife inside a leather sheath. Of course I pulled it out and cut myself but was terrified to admit what caused my finger to burst with blood.

“So you told them you were stung by a bee!” Oliver exclaims, having heard my lame excuse before. It never gets old.

What about the rug, they ask. That’s when I rolled myself inside a dusty rug at the back of Hebrew school and unspooled it noisily in the middle of class to the delight of my friends. The teacher threatened to call my parents so I sat by the phone for days and hung up on every caller, until one of their friends stopped by to check on us because they couldn’t get through.

These bits are immensely satisfying to Oliver and Laila, who really are angels. All they do is spill an occasional cup of juice or sneak an extra cookie. Maybe jump too exuberantly on the couch. And here I am confessing juvenile felonies.

Into our second week I still hadn’t run out of troublemaking yarns – maybe because I was a charter member of the Dennis the Menace generation in the 1960s, when kids like me made phony phone calls and tricked their older sister into eating dog pretzels.

I poured a whole box of colored crystals into our burning fireplace, causing a flame to jump onto our shag carpet until my dad stomped it out in a fit. I not-so-accidentally dropped my friend’s ring down the toilet, and had to buy him a new one from my allowance. I hid in a stuffy garment bag in the basement long enough to make everyone think I’d actually disappeared. I also ran up and down the street naked to avoid a bath, something my apartment-dwelling grandchildren could never fathom.

I even shoplifted my share of penny candy, until our local drugstore owner squeezed my arm and warned he’d put me in jail for grabbing a handful of spearmint leaves – that was enough to dissuade me from a life of thievery.

Most egregious, I ripped my chinos and bruised my knee leap-frogging a fire hydrant – then let my mother believe I’d been hit by a driver in a red car. She called the cops and never forgave the neighbor she suspected was behind the wheel.

Sometimes, my choice of words did me in. I had to apologize to a pair of twins in third grade after it got back to my mom that I told them they only had half a life span each. Fuming at my sisters for claiming I was a robot and had wires under my skin, I rooted through the dictionary for suitable comebacks, only to catch a scolding for claiming my siblings were prostitutes and harlots.

But the biggest crime was giving my folks lip and attitude. For that the punishment was severe – writing 100 times “I will be respectful to my mother and father and not talk back.” Oliver and Laila are aghast.

And there’s always the big one. That’s when I locked our dog Royal in my parents’ bedroom, not realizing theirs was the only door in the house that couldn’t be jimmied with the kitchen can opener.

The fire department was called and had to ladder up to the second story to free Royal, who had crapped on my parents expensive carpet. Thus I never got the bow-and-arrow set they bought me for Hannukah.

“That wouldn’t happen to us,” Laila says confidently, though not for the reason I assumed. “We celebrate Christmas and Hannukah – so we’d still get the bow-and-arrow.” With that, she and Oliver drift into the deep sleep of the innocent.


Allan Ripp runs a press relations firm in New York.


Read more like Alan Ripp’s stories of his childhood mischief and other contributions from Boomer readers, including nostalgia, essays, and short fiction, in

From Our Readers

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