Preheat oven to 375°F. Line a baking sheet with parchment paper or leave it ungreased.
In a small bowl, beat 8 oz. cream cheese until smooth. Add 1/2 cup granulated sugar, 2 tablespoons all purpose flour, and 1 teaspoon vanilla; mix until well combined. Set filling aside.
Open 1 tube crescent rolls and unroll the dough onto the prepared baking sheet, keeping the perforations intact. Press the seams and any holes together to form one single rectangle of dough.
Carefully spread the cream cheese filling down the center of the dough in a strip about 2–3 inches wide, leaving the long edges of dough free.
Evenly sprinkle 2 oz. chopped semi-sweet dark chocolate over the filling.
Using a sharp knife or pizza cutter, cut 1-inch-wide diagonal strips from each long side of the dough toward the filling, stopping where the filling begins so the center remains intact.
Starting at one short end, fold the first strip from the right over the filling at a 45° angle, then fold the first strip from the left, alternating sides down the length of the dough to form a braided pattern. Tuck or fold any excess dough at the ends as needed.
Bake 20 minutes, or until the crescent dough is golden and the filling is set. Remove from oven and let the danish cool completely on the baking sheet.
Transfer the cooled danish to a serving platter. In a small bowl, whisk together 1/2 cup powdered sugar and 1 teaspoon milk until smooth to make the icing.
Drizzle the icing over the cooled danish, cut into pieces, and serve.