The Costume Dilemma – Halloween Short Story

Jessie walked down the New York streets on the way home from school. Tomorrow night was Halloween and he still didn’t have any ideas and he was facing the costume dilemma horrors!

“Boo!” called out a voice to him. He jumped, then realized it was his friend, Maria.

“You got me!” he said in a joking manner.

“Seriously Jessie you need more confidence!”

“I know,” he replied. “Say, have you figured out your costume yet?”

She shook her head. “No, the costume dilemma strikes again and we’re running out of time. Say, did you know that Halloween used to be called All Hallows Eve, not Halloween?”

He smiled. “Yes, you’ve told me that three times now.”

“Sorry, I can be a know-it-all. Oh look, there’s Sam!”

Sam nearly walked past them, before finally stopping.

“Hi Sam!” she called out, but he ignored her.

“How’s it going?” asked Jessie, but no reply to that.

“I’m on the way to the store. Mum asked me to pick up some veggies for dinner.”

Maria looked annoyed. “Seriously, you’re going to have to learn to be more social.”

Jessie waved his hand at her. “Doesn’t matter. Do you know what your Halloween costume will be tomorrow night?”

Sam shrugged. “I’m going trick or treating with you but I’m not dressing up, so over the costume dilemma and needing to work out every year what to dress up in!.”

“You’re not,” Maria started to say, but Jessie tapped her on the shoulder. “Um, okay, see you tomorrow night!”

The next night, the three friends met up near the main entrance of Central Park. None of them wore a costume.

Maria looked worried. “We must be getting too old if we can’t figure out costumes.”

“Or we are just over the costume dilemma we face every single year,” said Jessie. “They kind of freak me out anyway.”

“Rwarrrrr!” screamed out a young child dressed as a lion.

Jessie ducked behind a park bench. “Help!”

Maria and Sam just laughed.

Then suddenly, the lights around the park went out. Ten seconds later, one of the most densely populated cities in the USA was quiet.

“Not again!” said Sam. “I heard this happened before.”

“Yes, there was a big one in 1965, but also a big power outage on the northeast side of New York in 2003.”

“You’re boring,” said Sam. “Let’s go.”

Maria looked annoyed.

“How? We can’t see anything,” said Jessie.

But then his entire body lit up as a bright skeleton. His two friends could now see him.

“Hey, cool costume!” said Sam, before looking down at himself. “Say what? I’m a King?”

“Oh, look at me, a clown?” Maria looked down at herself in dismay.

Jessie looked down at himself. “I think I’m scaring myself.” (is the costume dilemma getting weird?)

“Our costumes can’t be further from who we are.” Sam tugged at his crown but couldn’t get it off.

“Oh look, the power is coming back!”

The entire city lit up again. All the noise returned.

“Okay, first place to start!” The friends walked to a set of row houses on the block. Each door was lit up, the universal Halloween language to say, “Ring the bell!”

At the first door, Maria stood at the front. The door opened.

She didn’t know how it happened, but she blurted out, “Treat or Trick! Either way, you pay!” Then she cackled loudly like a clown.

The resident there loved their costumes and gave them extra candy.

At the next door, Jessie asked if he could be in front.

“Really? So not like you,” commented Sam, as he pressed the doorbell.

The door opened to an elderly lady. “Oh my goodness!” she said.

“Booooo,” said Jessie in a low voice. “I’m scary!”

They got extra candy again.

At the third door, Sam hung back.

“It’s your turn to go first,” said Maria, pointing at the door.

“Yes, a King is always first.” He stomped up to the door while Maria rang the doorbell.

An elderly man answered.

“Hello, my fine sir. I command thee to give us the entire bowl of candy as you’ll find no other party more deserving.”
The man divided the entire bowl of candy into their three trick or treat bags.

The children said thank you, and left.

“Wow, I feel like I have great confidence in my skeleton costume, maybe the costume dilemma I had wasn’t real” said Jessie.

Sam smiled. “I feel better knowing that I said hello first in my King costume. I mean, I usually don’t bother, but I think I can see the purpose of pleasantries now.”

Maria danced around the sidewalk. “I feel much freer now, like I don’t have to be a know-it-all in my clown’s costume.”

“I can’t wait until next year!” said Jessie. “Maybe I’ll be a zombie or we could face the costume dilemma again!”

His two friends laughed, as they’d never thought he’d choose to be that.

The three friends had fun racing around the neighborhood for the rest of the night, collecting plenty of treats, and pretending to be who they weren’t.

The End.


The Costume Dilemma Copyright Halloween Costume Themes