TO make dough:
1) Stir yeast, 1/2 teaspoon sugar, and water into a mixing bowl. Let sit for ten minutes until it’s foamy and all the yeast is dissolved.
2) Stir in milk, brown sugar, sugar, eggs, vanilla, and salt. Once combined, stir in flour one cup at a time.
3) Add dough to a stand mixer and mix with the dough hook for 4-5 minutes until the dough is soft and combined well. You can also do this by hand by working the dough vigorously in the bowl.
4) Add softened butter and let the dough hook beat it into the dough. If they dough is very stick, add another 1/4-1/2 cup flour. It’s okay if the dough is a bit sticky though. Beat with dough hook for another 4-5 minutes.
5) Add dough to a clean metal bowl and dust with flour. Cover and let rise for two hours until it doubles in size.
To make filling:
1) Cut dates in half and remove pits. Add to a food processor with sugar and pulse until combined.
2) Add to a bowl along with other filling ingredients except for the brown sugar. Stir to combine.
To make rolls:
1) Turn dough out onto a floured surface. Roll into a large rectangle. It should be about twice as long as it is wide so 12×24 is a good goal.
2) Sprinkle date filling over the surface of the dough. Then sprinkle entire surface with brown sugar.
3) Roll dough starting from the short end so you are creating as many layers as possible. Roll tightly and once rolled, try to even out the roll so each part is the same thickness.
4) Cut rolls into 8 even pieces and add to a large, lightly buttered baking dish.
5) Cover and let rise for an hour.
6) Bake rolls in a preheated 375 degree oven for 25-30 minutes until they are nicely browned around the edges.
7) Let rolls cool for about 30 minutes and then drizzle with icing.
These are best served warm. If you are serving them the next day, it’s not a bad idea to microwave them for 10-15 seconds just to warm them up.