Challenges & Obstacle Courses – Tolentino Teaching https://briantolentino.com Thu, 02 Apr 2026 23:03:08 +0000 en-US hourly 1 https://wordpress.org/?v=6.9.4 Board Tales: Collaborative Storytelling https://briantolentino.com/board-tales-collaborative-storytelling/ Thu, 12 Mar 2026 16:29:12 +0000 https://briantolentino.com/?p=13789 The Sketch: Select 1–4 students to come to the board. They have 5 minutes to collaboratively create a scene (a landscape, character, monster, etc.)

The Prompt: Once finished, the rest of the class must use the drawing as the setting or subject for a creative writing piece. 

Worksheet:

Board Tales Collaborative StorytellingDownload

Here is an example drawing by a class of sixth graders:

]]> The “10 Random Things” Story Challenge #2 https://briantolentino.com/the-10-random-things-story-challenge-2/ Tue, 10 Mar 2026 00:28:10 +0000 https://briantolentino.com/?p=13772 Your challenge is to write a short story that naturally incorporates all 10 things below. Some of them may seem unrelated—but your job is to make them fit together in a creative way.

Worksheet:

The 10 Random Things Story Challenge #2Download
]]> The “10 Random Things” Story Challenge! https://briantolentino.com/the-10-random-things-story-challenge/ Mon, 09 Mar 2026 00:06:28 +0000 https://briantolentino.com/?p=13768 Your challenge is to write a short story that naturally incorporates all 10 things below. Some of them may seem unrelated—but your job is to make them fit together in a creative way.

Worksheet:

The 10 Random Things Story ChallengeDownload
]]> 20 Creative Writing Prompts for Middle School Students! https://briantolentino.com/20-creative-writing-prompts-for-middle-school-students/ Sat, 07 Mar 2026 13:53:19 +0000 https://briantolentino.com/?p=13718 These prompts work great as creative writing activities, quick class finishers, or even emergency sub plans when you need something engaging and meaningful for students.

  1. 10-Sentence Story Challenge: School Mystery Edition!

Video:

Worksheet:

10-Sentence-Story-Challenge-6-4Download

2) Creative Writing Prompt: The Day the ROBOTS Took Over! 

Video:

Worksheet:

The-Day-the-Robots-Took-OverDownload

3) Writing Challenge: My Life as a Metaphor!

Worksheet:

Writing-Challenge-My-Life-as-a-Metaphor-10-Sentence-StoryDownload

4) Write a Letter to a Fictional Character!

Video:

Worksheet:

Write-a-Letter-to-a-Fictional-CharacterDownload

5) The Ultimate Creative Writing Challenge (Vary Sentence Length)

Video:

Worksheet:

The-Ultimate-Writing-Challenge-Vary-Sentence-LengthsDownload

6) Write A Story Inspired by a Song!

Video:

Worksheet:

Write-a-Creative-Story-in-Response-to-a-Song-3Download

7) 10-Sentence Story Challenge: Messi vs. Ronaldo Showdown!

Video:

Worksheet:

10-Sentence-Story-Challenge-Messi-vs.-Ronaldo-Showdown-3Download

8) 10-Sentence Emoji Challenge!

Worksheet:

10-Sentence-EMOJI-STORY-Challenge-2Download

9) Argue why you should be on the “nice” list!

Video:

Worksheet:

Argue-Why-You-Should-Be-on-the-Nice-List-3Download

10) Write a Story that Includes a Monkey, a Manicure, a Mermaid, and a Mango!

Video:

Worksheet:

Write-a-Story-That-Includes-a-Monkey-a-Manicure-a-Mermaid-and-a-MangoDownload

11) Writing Prompt: The Town of 67

Worksheet:

The-Town-of-67-2Download

12) Writing Prompt: The Whispering Manor

Video:

Worksheet:

The-Whispering-ManorDownload

13) “About Me” TikTok Script: 10-Sentence Challenge!

Worksheet:

About-Me-TikTok-Script-2Download

14) Creative Writing Prompt: Lost in Space!

Worksheet:

Lost-in-Space-Creative-Writing-PromptDownload

15) Microfiction Challenge: Write 10 Short Stories!

Video:

Worksheet:

Microfiction-Challenge-2-5-2Download

16) 10-Sentence Onomatopoeia Challenge!

Worksheet:

10-Sentence-Onomatopoeia-ChallengeDownload

17: 20-Sentence Story Challenge (Plot Rollercoaster)

Video:

Worksheet:

20-Sentence-Story-Challenge-Plot-RollercoasterDownload

18: Writing Prompt: My Trip to PARIS!

Video:

Worksheet:

My-Trip-to-ParisDownload

19) Writing Challenge: My Life in Similes (10-Sentence Story)

Writing-Challenge-My-Life-in-SimilesDownload

20: Sentence Structure Challenge!

Worksheet:

Sentence-Structure-Challenge-2Download
]]> Power Verb Story Challenge! https://briantolentino.com/power-verb-story-challenge/ Mon, 02 Mar 2026 14:04:38 +0000 https://briantolentino.com/?p=13701 Worksheet:

Power Verb Story Challenge-2Download

More Power Verb Activities Here:

Power Verbs Activities
]]> Partner Word Story Challenge! https://briantolentino.com/partner-word-story-challenge/ Mon, 20 Oct 2025 13:11:25 +0000 https://briantolentino.com/?p=13151 For this activity, you’ll write a 10-sentence story—but with a catch. Your partner will choose one word that you must include in each sentence. You’ll have a word bank of 30 words to choose from, and your partner gets to decide which words you have to use.

Worksheet:

Partner Word Story ChallengeDownload
]]> “You vs. You” Writing Quest: Overcoming Doubt in Another World or Era https://briantolentino.com/you-vs-you-writing-quest-overcoming-doubt-in-another-world-or-era/ Mon, 05 May 2025 02:47:17 +0000 https://briantolentino.com/?p=8311 Video:

Worksheet Here:

“You vs. You” Writing Quest Overcoming Doubt in Another World or EraDownload

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]]> Creative Story Challenge: Who’s the Author? https://briantolentino.com/creative-story-challenge-whos-the-author/ Sun, 04 May 2025 04:12:00 +0000 https://briantolentino.com/?p=8278 Video Here:

Worksheet:

Creative Writing Challenge Who’s the AuthorDownload

Donate Here:

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]]> Writing Prompt: Journal Entry from a Movie Character https://briantolentino.com/writing-prompt-journal-entry-from-a-movie-character/ Thu, 01 May 2025 20:56:35 +0000 https://briantolentino.com/?p=8243

Worksheet:

Write a Journal Entry From a Movie CharacterDownload

Donate Here:

Donate

]]> The Ultimate Writing Challenge (Vary Sentence Length) https://briantolentino.com/the-ultimate-writing-challenge-vary-sentence-length/ Sun, 27 Apr 2025 13:39:11 +0000 https://briantolentino.com/?p=8200 Writers often vary their sentence lengths to create rhythm.
A long, winding sentence — one that stretches, elaborates, and meanders on and on — can set a flowing, thoughtful pace.
Follow that with a short sentence, and suddenly, you have music.
Hear it? Feel the rhythm?

Your mission: Write a short story — but with a twist.
You must follow an exact word count for each sentence.
That’s right: every sentence will have a set number of words, and your story must be exactly 12 sentences long.
Here’s the challenge: stick to the word counts given for each sentence below.

Video:

Worksheet:

The Ultimate Writing Challenge (Vary Sentence Lengths)Download

Donate Here:

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