Every week, Reedsy Prompts hosts a creative writing contest that challenges writers to craft stories inspired by unique prompts. While I don’t participate every week, I love diving into these challenges when inspiration strikes. Whenever I submit a story, I’ll share it here for you to enjoy!

#285: Flash(back)

Specific Prompt I Chose

For this challenge, I selected the prompt:

“Write a story in the form of a landline phone conversation.”

Without further ado, here’s my submission—a heartwarming tech support story about a grandmother’s first adventure with a computer. I hope you enjoy reading it as much as I enjoyed writing it!

“Thank you for calling Gateway technical support, this is Mike speaking. How can I help you today?”

Mike adjusted his headset, already anticipating another Windows 2000 migration headache. The queue had been relentless since the Y2K dust settled. But the voice that came through was warm, slightly breathy, backed by the scratchy sounds of a Dean Martin song spinning on a vinyl record.

“Oh, hello dear. I’m having trouble with my new Gateway computer. It just arrived today – what a lovely birthday surprise! When I saw those black and white spotted boxes on my doorstep, I thought one of daddy’s Holstein cows had left me a present!” She laughed at her own joke, the kind of genuine laugh that made Mike’s cursor pause over the ticket system.

“Two boxes,” she continued, “One’s got this television box thing that’s heavy as my old Zenith, and the other’s got the… what do you call it… the thinking part?”

“That would be the tower, ma’am,” Mike said, finding himself smiling. “And the TV-looking box is actually called a monitor. But tell me more about your setup. May I have your name?”

“Dorothy Miller. Seventy-two today!” The music in the background swelled with perfect timing. “My children went together on this Gateway. Said they got me the bigger TV box – nineteen inches! – so these old eyes won’t have to squint. They want me to be able to email my grandbabies!”

Dorothy’s description of her setup was interrupted by a sharp ‘ding’ from somewhere in her kitchen. “Oh! That’ll be my birthday cake. Would you mind holding for just a minute, dear? Can’t have my maple walnut cake burning on account of this computer business.”

“Of course, take your time,” Mike said, hearing the phone being set down, Dean Martin still crooning in the background. He could make out the distant sounds of an oven door, the clatter of a pan, and Dorothy humming along with the music.

“There we go,” she returned slightly breathless. “Sorry about that. My mother always said you can’t serve a burnt cake, even on your own birthday! Now, where were we with this TV box?”

Mike guided her through connecting the power cables, which Dorothy declared looked “like the hoses we used to milk the cows—everything fits snugly where it belongs.” Just as they were about to power everything up, a voice called through what sounded like a screen door.

“Dorothy! Happy birthday!”

“Oh! That’s Betty from next door. Betty! Come see my new computer! My children sent it!”

Mike heard muffled conversation, Dorothy proudly describing her “Holstein-spotted boxes” to Betty, who seemed suitably impressed. After Betty left (”She’s off to her bridge club – they’ll all be jealous of my new gadget!”), they returned to setup.

The Windows startup sequence fascinated Dorothy. “Look at all those little pictures dancing across the TV box! Reminds me of my dance students lining up for the Virginia Reel.”

When it came time to use the mouse, Dorothy’s farming background provided more colorful analogies. “This little critter’s harder to direct than a cat in a rainstorm!” she declared, but soon got the hang of it. “Oh! It’s like leading in a dance – you have to guide it gentle-like.”

After adjusting the display settings to make the text more readable, Mike had to break the news about rebooting. “The computer needs to take a little nap to remember these changes, Dorothy.”

“A nap? Will it forget all our hard work?” she asked, concerned. “Like when the power goes out and Betty’s answering machine loses all its messages?”

“Not at all,” Mike assured her. “Think of it more like letting a cake cool before frosting it – everything will be right there waiting for us.”

During the reboot, another visitor’s voice called through her window, breaking into song: “Happy Birthday to youuuu!”

“That’s Margaret,” Dorothy explained, laughing. “She sang opera in college – never lets us forget it! Thank you, Margaret!” she called back. “I’m learning about computers!” Margaret’s opera voice carried through the screen door, a reminder of how even the smallest communities had their stars.

“You tell that young man helping you that you need to check your email every day!” Margaret’s voice carried through clearly.

“Every day?” Dorothy sounded worried. “Like feeding the chickens?”

Mike chuckled. “Only when you want to, Dorothy. The messages will wait for you, just like letters in a mailbox.”

When they finally got to setting up her email account, Dorothy dictated her first message to her grandchildren: “Dear Gavin and Lizzy, Your old grandmother has entered the modern age! This nice young man Mike is helping me learn about this TV box that sends magic letters through the air—imagine that! You will probably think your grandma’s a wizard! Lizzy, I’ve still got your quilt in progress, and Gavin, you’ll have to teach me more about this internet business when you visit. Love and kisses, Grandma Dorothy.”

Just before they finished, Dorothy’s attention seemed drawn away again. “Oh! I should put the frosting on before it gets too cool. Like I said earlier, some things just can’t wait – it will just take a minute.”

“Go ahead,” Mike said, smiling. “The TV box will be here when you get back.”

Dorothy set the phone down again, and Mike could hear her humming along with Dean Martin as she worked. When she returned, there was a satisfaction in her voice that went beyond computers. “There! A proper birthday cake needs proper frosting. Just like a proper grandmother needs to learn these new things to keep up with her grandbabies.”

When the “Message Sent” confirmation appeared, Dorothy clapped her hands together, her laughter bubbling through the line. “Wait till Betty sees this! She’s still trying to figure out her answering machine—and here I am, sending magic letters in no time at all!”

“You’re a natural, Dorothy,” Mike said, meaning it.

“And you’re a wonderful teacher, Mike. Patient, just like I had to be with my dance students.” There was a knowing pause. “Now promise me you’ll call your grandmother when you get home tonight. No fancy TV boxes needed for that – just a telephone and a loving heart.”

Her words lingered, stirring a warmth in Mike’s chest—a reminder of the phone calls he’d been meaning to make but always put off. That evening, he walked into his apartment and, before even taking off his coat, picked up his cordless phone and dialed a number he hadn’t called in months.

“Grandma? It’s Mike.” The familiar warmth of her voice, slightly startled but immediately welcoming, caught in his throat. Through her kitchen window, he visualized that old pendulum clock would be ticking, marking time in the maple-scented air. “I… I miss you.”

REFLECTIONS

This story was such a joy to write!

When I saw the prompt, I immediately thought about how technology can connect people in surprising ways, especially across generations. I wanted to tell a heartwarming tech support story that blended humor, nostalgia, and a sense of discovery. Dorothy’s character came to life so vividly for me—her determination to learn something new and her colorful personality made her such a delight to write.

Researching the era of early home computers brought back a flood of memories, and it was fun revisiting the quirky charm of Gateway’s iconic cow-patterned boxes. I also loved exploring the dynamic between Dorothy and Mike, and how their interaction grows from a routine tech support call into something meaningful.

At its heart, Help Desk is a story about connection—between generations, between tradition and technology, and between people who take the time to truly listen to one another.

What do you think? Does Dorothy’s journey remind you of anyone in your life? I’d love to hear your thoughts in the comments below!

If you’d like to try your hand at creative writing, check out Reedsy Prompts for weekly inspiration!