Make the Dough

Combine some of the dry ingredients. In a large bowl using a whisk combine the yeast, sugar, salt and 1 cup of the flour.

Add wet ingredients. Add the warm milk, 2 eggs, 4 tablespoons of olive oil, then the honey and vanilla. (Add the olive oil first, then use the same measuring spoon to add the honey – residual oil on the spoon will make the honey slide right out.)

Vigorously mix the ingredients until smooth. Scrape the sides of the bowl halfway through, about 3 minutes.

Add the rest of the flour. Add the remaining flour, 1/2 cup at a time, switching to a wooden spoon when the dough becomes too thick for the whisk. Continue mixing the dough until it is too stiff to stir.

Knead. Turn the dough out onto a lightly floured surface and knead until soft and springy, about 4 minutes. If the dough is sticky, dust with flour 1 tablespoon at a time – just enough to prevent it from sticking to the surface. The dough is done when it’s smooth and small air bubbles show under the skin. If you press your thumb into it the impression should bounce back. This is a slightly firm dough, which is exactly what you want for easy braiding later on.

First rise. Place the dough in a deep container greased with 1 tsp of olive oil. Turn the dough once to coat the top and cover with plastic wrap. Allow it to rise at room temperature until doubled in bulk, about 1 1/2 to 2 hours.

Prep your tools. Line a baking sheet with parchment paper. You are going to assemble the bear directly on the baking sheet.

Deflate the dough. Gently deflate the dough by pressing your fingers into it, then turn it out onto a lightly floured surface.

Shape the Bear and Bake

Get a sharp knife. To assemble the bear you’ll need to cut the dough using a sharp knife (so divide the dough before working with a toddler or young child if that is what you are doing).

Cut the dough in half. One half of the dough is going to be the teddy bear’s body. Shape it into a large ball and place it in the center of your lined baking sheet.

Cut the remaining piece of dough in half. One half of this piece is going to be the teddy bear’s head. Shape it into a ball and place it just above the body, using a little bit of water to help the two pieces stick together if necessary.

Cut off about 1/3 of the remaining piece of dough. Divide into two small balls (the ears) and one smaller ball (the nose).

The last piece of dough will form the arms and legs. Cut it into four pieces, roll into balls, then attach to the teddy bear’s body. You can make the legs bigger if you want by using more of this portion of dough for the legs.

Preheat your oven to 350 degrees F. By the time the bear finishes the second rise your oven will likely be ready for baking.

Let the dough do a second rise. Cover the bear loosely with plastic wrap and let rise until almost doubled in bulk, 30 to 40 minutes.

Add the eyes and belly button. With a sharp knife cut small slits where the eyes and belly button will be, then insert raisins, dried cranberries, or dried blueberries. (Any kind of dried fruit will work.) Stick a raisin or blueberry on the nose. You can also make a series of little holes vertically down the belly and insert raisins or dried cranberries/blueberries like the teddy bear is wearing a sweater and these are the buttons.

Add the egg glaze. Whisk together 1 egg and 1 teaspoon of olive oil, this is going to be the glaze for your bread. Gently brush the dough with a thick layer of it. (This is the same process as if you were making a regular challah.)

Bake. Place the dough in the oven and bake for 30 to 35 minutes, or until the bread is a deep golden brown and sounds hollow when you thump it on the bottom.

Cool. Transfer to a baking rack to cool. Allow to cool completely before slicing – or at least wait until it’s warm, not hot – then enjoy!