Step 1

Place yeast and sugar in a small bowl. Add lukewarm water and set aside until foamy, around 5-10 minutes.

Step 2

In a stand mixer fitted with dough hook or a large bowl, mix together flours, sugar, vanilla and cinnamon. Start with 3 1/2 cups of flour, and add more later if dough seems too sticky. Add milk and olive oil.

Step 3

Add the eggs one at a time.

Step 4

When the dough begins to come together, after about 3-5 minutes, turn out onto a floured surface and knead vigorously for 5-10 minutes. Or if using a stand mixer, switch to high and mix another 4-5 minutes. Dough should be shiny, elastic and very soft when it is done. If dough is sticking too much, add more flour 1/4 cup at a time until dough is not longer sticking.

Step 5

Place dough in a greased bowl with a damp towel on top. Allow to 1-2 hours.

Step 6

While dough is rising, make filling.

Step 7

Combine all filling ingredient in a saucepan over medium heat. Bring to a boil, then reduce for 10 minutes, until liquid has reduced to slightly more than half. Allow to cool slightly. Place in food processor and pulse.

Step 8

*Note: you can also replace filling with store-bought fig jam.

Step 9

Preheat oven to 350 degrees.

Step 10

Cut dough into two parts. Roll out each section of dough until it is a rectangular-like shape. Spread with filling. Working from the shorter side, roll up dough using quick fingers, like you would in order to make cinnamon rolls.

Step 11

Once the dough is a long log, cut it straight down the middle so the filling is exposed. Secure the ends on one side, and twist both the pieces . Pinch and secure at the other end.

Step 12

Place in a greased loaf pan. Allow to rise another 10-20 minutes. Sprinkle top with slivered almonds if desired (this step is optional).

Step 13

Bake for 30-35 minutes.

Step 14

Top with date honey if desired.