Flash Fiction Friday: The Hobo and The Prep

Welcome back to Flash Fiction Friday, Arrowheads! Today, I’m sharing with you one of the most random short stories I’ve ever penned. I was probably in the 8th or 9th grade when I first wrote this story on Quizilla: a creative writing website that is no longer in service. As a disclaimer, I want to mention that this story is written from a humorous perspective; I am not aiming to insult or offend homeless people or rich folk. So, here we go: the three-part story of “The Hobo and the Prep”!

The Hobo and the Prep


Part 1:

One day, Tiffany the Prep was driving down a bustling street in New York City, when a hobo darted out in front of her Lamborghini. Tiffany screamed, “Stupid hobo!” and slammed on brakes, swerving to miss the homeless man. Upon the cursing and unfriendly hand gestures by other drivers, Tiffany bolted from her car to find the hobo sprawled out in the middle of the street.

The hobo peered up at her in awe and said, “Howdy, Little Miss Fancy! What’s your name? I’m Hobo Flynn!”

Repulsed, Tiffany flipped her sleek bleach blonde hair and replied, “Like, have you never heard of me? I’m Tiffany Preppington!”

Hobo Flynn gazed at her as if he were trying to remember something, causing Tiffany to back away to her car. Finally he spoke, his raspy voice lighting with excitement, “Tiffany? You’re the one I went to the prom with!”

Tiffany shuddered at the mention, darting back to the convertible. “I went to the prom with Chad Hawtson, you idiotic hobo!” she yelled as she started the engine and sped off. This, however, wasn’t enough to stop Hobo Flynn, as he stealthily jumped into the back seat of the car, riding all the way to her house.

When Tiffany returned home, she sifted through her Michael Kors handbag for her house key. Hobo Flynn crouched behind the bushes, stalking her. Tiffany opened the door and walked into the mansion. Hobo Flynn waited until the coast was clear, then followed her in.

Thirty minutes later, Tiffany was enjoying her afternoon, watching Keeping up with the Kardashians, when she heard a ruckus in the kitchen.

“Manson, is that you in there?” she yelled to her butler, for there was a chance he was preparing dinner. The lack of an answer startled Tiffany, so she decided to head into the kitchen herself. By the time she walked through the door, Hobo Flynn had a seven-layer sandwich before him. Smiling up at her, he asked, “Got any pickles? I like me some pickles!”

Tiffany screamed, pulling out her iPhone to call the police. Being that the Preppingtons were the richest family in the country, the authorities arrived in no time. They promptly arrested Hobo Flynn, and the judge sentenced him to the maximum sentence of ten years in prison. The last thing Hobo Flynn ever said to Tiffany was, “See you at the prom this year. I’ll break out just to go with you, Honey!”

Tiffany threw up and went to bed, exhausted by the terrors the day had brought her. She woke up the following morning, convinced it had all been a nightmare. As weeks passed by, Tiffany remained unfazed by the stalking incident. However, when Manson brought her the mail at breakfast one morning, she found a letter addressed to herself and began to read:

Dear Tiffany,

Sorry that it took me so long to write, but the prison guards won’t trust me with a pen. Hope to see you at the prom, Baby!

Love, Hobo Flynn


Part 2:

It had been months since Hobo Flynn’s arrest for stalking Tiffany Preppington, the love of his life. As he sulked in his jail cell, his brooding, muscular cellmate asked, “What’s wrong, buddy?”

Hobo Flynn didn’t respond. Instead, he pulled Tiffany’s photograph (which he stole from her mansion) from his pocket , and held it close.

“Flynn! Tell me, or I’ll beat the answer out of you!” the cellmate commanded.

“Here,” Hobo Flynn said, handing him the picture. His cellmate studied the picture, failing to hide his disgust. “Looks like some prep to me!”

Hobo Flynn snatched the picture away, crestfallen. “She’s not a prep! She’s my Little Miss Fancy—soon to be prom date!” He buried his head in his hands.

His cellmate offered a semi-sympathetic look. “Good luck with that, bud.”

Hobo Flynn had never been more upset in his life—minus the time the bank repossessed his cardboard box—but he loved Tiffany. So, without further ado, he decided to ask his cellmate for a favor. “Will you help me break out?”


“Will you help me break out?” Hobo Flynn repeated, his dirty, scarred face the emblem of seriousness.

The cellmate contemplated the request. The prison hadn’t had much excitement lately, and he was skilled at breaking into buildings. Perhaps he could break out, too. “Okay, I’m in!”

“Awesome! So, I’ll get this shovel,” Hobo Flynn said, pulling out a plastic spoon, “and you find something else so we can tunnel out of here!”

His cellmate face-palmed himself. “Hobo, we’re not tunneling out of here!” He grabbed onto the prison bars, straining to pull them a body-width apart. “Come on, let’s go!”

Hobo Flynn discarded his spoon without question, and headed out into the hallway after his cellmate. Nevertheless, they were soon stopped by a prison guard.

“Dang, I forgot about him! Flynn, what are we gonna do?” the cellmate whispered.

“Uh, I don’t know!” Hobo Flynn quivered, his belly rumbling with nerves. He was so nervous, in fact, that a fart of explosive proportions escaped.

“Lordy, that stinks!” the prison guard shouted. He attempted to fan away the stench, but instead fell to the ground in a state of unconsciousness. Hobo Flynn’s cellmate was full of gratitude, and motioned him to follow him out of the prison and past the gate.

“We’re finally out!” his cellmate cheered. “Well, I’ll see you later, Hobo Flynn. I’ve gotta go.”

“Go where?” Hobo Flynn asked, curious.

“I just gotta go…” the cellmate said, running off into the distance.

Hobo Flynn’s top priority upon escaping was to locate Tiffany’s mansion. He remembered exactly where it was—a big, pink mansion on the outskirts of New York City.

Hobo Flynn navigated his way around the city for days, until he spotted the eyesore of a mansion. Upon ringing the doorbell, Manson the Butler greeted him.

“Hello Sir, who are you?” Manson inquired in his British accent. He sprayed Hobo Flynn with Febreeze as soon as he caught a whiff of him.

“My name’s Hobo Flynn! I’m here to see Tiffany Preppington!” Hobo Flynn blushed at the mention, eager to see the love of his life again.

Manson produced a condescending laugh. “Tiffany Preppington? She moved to Los Angeles when she found out you loved her.”

Enveloped in devastation, Hobo Flynn sulked all the way back to the prison, where he took his jail cell back. Anything was better than living in the dumpsters.

Part Three:

Fifteen years have passed since Hobo Flynn returned to prison. The day his ten-year sentence was up, Hobo Flynn ventured back on his search for Tiffany. Though he was still depressed over the matter, he’s turned a new leaf. When he was released, he took up hitchhiking, traveling all over the United States in search for his lost love. Upon searching for food in West Virginia, Hobo Flynn came across running oil. Soon after, he spotted a man in a suit who had a flat tire, and showed him the discovery. The man paid Hobo Flynn five billion dollars for the area where his new cardboard box sat. Now that Hobo Flynn is rich, tabloids surface information on his new identity: The Hobo Formerly Known as Flynn.

With his newfound money, Hobo (as we all must refer to him now, or he’ll sue) decided to move to Los Angeles. He wanted to marry a model, and he figured that’s where he would find one. While taking his limo out for a Sunday drive down Rodeo Drive, the driver slams on brakes. Hobo yells viciously at the driver, demanding an answer as to why they stopped. The driver mentions something about a homeless girl almost getting hit. A flashback crosses Hobo’s mind of fifteen years earlier; he met Tiffany the same way back in New York City.

Hobo jumps out of his eighty-foot limo, rushing to find the victim. Next to the front left tire, he finds a bleach blonde girl in a filthy Prada ensemble. Apparently, she was still obsessed with being in style, even after losing all of her fortune.

“Howdy, Little Miss Fancy!” Hobo says, helping her up. Tears descend from Tiffany’s eyes, mascara running down her cheeks. Hobo peers at her pale, bony face, knowing that she’s been suffering for a while.

“Is that you, Hobo Flynn?”

Hobo smiles humbly, answering, “The Hobo formerly known as Flynn.”

Tiffany swipes at the tears. “I am so sorry for treating you with so little respect back then. Now everything has changed. I wouldn’t blame you for treating me the same way. You probably don’t want anything to do with me now—a rich guy like Mr. Hobo would never be seen with a Preppington these days. We’re worse than common folk,” she apologizes, collapsing on the curb to sob.

Hobo crouches on the corner beside her. “Don’t say that, Miss Tiffany. I’m still the same Hobo Flynn that you met back then. All that’s happened is that I got rich, changed my name, ate ‘til I was full for the first time in years, and got me some new dentures.” He opens his mouth to show her, his new teeth brighter than the shining sun.

Tiffany manages a laugh, hoisting herself up to leave. “Well, thank you for making sure I was okay, Mr. Hobo, but I must be on my way back to my box.”

She starts to walk off, but Hobo grabs her hand. “I can manage to buy you a house, Tiffany. We share a bond like no other. I only owe it to you.”

Overwhelmed with gratitude, Tiffany pulls Hobo in for a hug. She never appreciated anyone more than him. It’s the start of a brand new, revolutionary friendship: the hobo and the prep.

©Allyson Kennedy, 2017. All rights reserved.

If you made it to the end of this 1000+ word work of weirdness, God bless you! XD I hope you enjoyed it, and make sure to check out another Flash Fiction Friday soon!

-Allyson 😀

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As an author and blogger, my goal is to teach writers that there is a way to write realistic, thought-provoking, redemptive Christian fiction that honors God while not sugarcoating the realities of the world. 

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