Cut the kabocha squash into big pieces and place in a heat resistant bowl. Cover with plastic wrap and microwave until the kabocha squash softens.
Remove the peel. The peel will be used to make the jack-o-lantern eyes and mouth, so try not to rip it.
Add sugar and then mash the kabocha squash with a fork as smooth as possible.
Take the mix from Step 4 and tightly wrap it into a ball using plastic wrap.
Wet your hands and smooth out the kabocha squash dough.
Use scissors or a knife to cut the eyes and mouth from the kabocha squash peel.
If you have pumpkin seeds, you could use them to make stems, then stick the eyes and mouth, and it's done.
Story Behind this Recipe
We make these every year at my house around Halloween.
I used a sweet kuri kabocha squash. Adjust the amount of sugar based on the sweetness of the kabocha squash. You could also omit the sugar completely. If you want to make them even softer, mix in with milk.