NYC Midnight - 500 Word Microfiction Challenge (2026)
Genre: Romance
Word: shoebox
Action: Investigating
Wanderlust
A woman is inspired to take a chance on love after the passing of her unconventional, flighty, scoundrel-of-a-grandma.
—
“Grandma Jo has more secrets than hairs on our heads,” my mom once said as she flicked one of my spiral red curls.
I didn’t understand it then, but her pale skin, freckles, and shock of bright hair made my mother a source of gossip around her small Massachusetts town. Travelers came and went, and as I realized the rarity of my own red hair—along with the reputation of my grandmother and the lack of a grandfather—I eventually grasped the meaning.
Grandma was a beauty, a gambler, and perhaps most importantly, a scoundrel. The day my mom turned eighteen, grandma Jo was gone with the wind, leaving behind sheds of broken down tractors, moth-eaten wardrobes, unplowed farmfields, and a thousand rumors at her back. An occasional envelope or postcard was the only proof of life, sometimes accompanied by a cheap trinket or promises of finally hitting a jackpot.
I’ve met a rich man, I remember reading once, my eyes wide at a fluttering (counterfeit) $100 bill falling to the ground.
Though the cards reeked of cigarettes, I always dug them out of the garbage after my parents went to sleep, staring at the city skylines and silhouettes from grandma’s adventures. I imagined myself getting out of my small town. Living glamorously, with sequin dresses in Vegas, a Virginia Slim held up between my fingers. Laughing with strangers over sour cocktails in London.
Only I never did. I settled down quickly, married and divorced in that same small town, and I never met Jo.
No one knew my grandma had passed until we were notified of a delinquent storage locker out in California. Due to her hedonistic lifestyle, my parents and I flew across the country, fastening nitrile gloves and face masks to investigate like it was a crime scene, rather than the musty remnants of a sweet old lady’s life.
I pull a shoebox from a low shelf and brace for what may lay inside. Drugs? Stashes of real $100 bills? …Sex things? To my surprise, when I remove the top, my eye is first drawn to a lock of curly red hair. I hold it up to the light, like a scientist in a lab, and my mother freezes in place, watching.
We huddle over the box, full of old photographs and letters, not unlike the postcards I had secretly treasured. The letters have all been addressed, “My dearest Jo.”
Though the photos are black and white and willowy with age, our hearts leap at the sight of a handsome Irishman labeled Rory Byrne. We dig deeper into the box, finding promises to be together. Undying declarations of love and plans for the future.
…And then we find another shoebox. Another lock of hair, dark this time, and more letters detailing passionate starlit evenings sipping champagne with Robert Hannigan.
Even more boxes await.
Jo may have been a scoundrel. A terrible mother. But she was a hopeless romantic at heart.
I book that trip to London the next day.
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