Make the dough: Mix semolina and flour in a bowl. Rub in softened butter until the mixture is crumbly. Add powdered sugar and vanilla. Slowly add milk until dough sticks together but isn’t sticky. Cover and rest 30 minutes.
Prepare the filling: Melt butter in a small pan. Add dates and cinnamon. Cook 5–7 minutes until soft and paste-like. Stir in orange blossom water if using. Let it cool.
Shape the cookies: Take a walnut-sized piece of dough. Flatten it in your palm, add a small amount of date filling, and fold the dough around it. Seal completely. Press into a Maamoul cookie mold or shape by hand.
Bake: Preheat oven to 350°F (175°C). Place cookies on a parchment-lined tray. Bake 15–20 minutes until edges are lightly golden.
Finish: Let cookies cool. Dust generously with powdered sugar before serving.