Drawing Challenge #06: Draw the First Thing Pinterest Shows You

#W2DTogether Challenge #6

Original Run: Sunday, October 19, 2025 – Sunday, October 26, 2025

Hi everyone!

It’s time for our sixth #W2DTogether drawing challenge! This week’s challenge is going to be a little unpredictable… but it’s going to be a lot of fun! :D

If you are new here and want to see our journey so far, check out all the previous challenges here.

Now, let’s see what the algorithm has in store for us!

The Challenge

Challenge number 6: Draw the First Thing Pinterest Shows You

Here’s how it works:

Open Pinterest: The platform already knows your taste and what inspires you.
The Refresh Rule: Refresh your homepage and draw the very first image it shows you.
Keep it going: Refresh again and draw the next “first thing.” Do this until you have enough elements to build a full artwork.

The Twist: Connect the “Randomness“: Try to connect all your small drawings into one bigger, cohesive art piece. The goal is to make it look like the composition was intentional from the start, even though the subjects came from random prompts. It’s fascinating to see how your own taste and the algorithm shape your creativity!

Turn random image references into a wonderful piece of art. Let Pinterest lead the way, but make the final drawing uniquely yours.

Tips for Success

Don’t Cheat: If you get something weird, try to find a way to incorporate it! (Though if you really hate it, I’ll allow one extra refresh 😜).
Composition is Key: Think about how a portrait might interact with an object or a landscape you pulled from a different refresh.
Algorithm Insight: This challenge is a “mirror” to your own artistic interests—pay attention to what your feed is telling you!

The Rules

Must be YOUR drawing.
Medium: Drawings only (pencil, pen, colored pencils, markers, or digital). No paintings.
No AI art.
Objective: Combine multiple “first-pin” refreshes into one connected artwork.
All skill levels welcome.

Where It All Started

This challenge was originally posted on Reddit. You can see the original thread to find out what “weird” things the Pinterest algorithm threw at our community: