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Prepare the Brownies- Preheat oven to 325 degrees F. Line a 9x13-inch pan with foil, with enough to hang over all four sides. Butter the foil. In a medium glass bowl, melt the chocolate in the microwave in 30-second increments, stirring after each, until melted and smooth. Set aside to cool slightly. In a large mixing bowl, mix the butter and brown sugar with an electric mixer on medium speed until light and fluffy. Beat in the eggs and vanilla extract, scraping the bowl as needed. Mix in the melted chocolate until combined. Reduce the speed to low, add the flour and mix just until combined (don't over-mix). Spread the batter into the prepared pan. Bake 25 to 35 minutes, or until a toothpick inserted into the center comes out clean. Let cool completely.
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Prepare the Cookie Dough- In a medium bowl, use an electric mixer on medium speed to combine the butter and both sugars. Add the milk and vanilla and mix until combined. Reduce the speed to low and mix in the flour just until combined. Using a rubber spatula, stir in the chocolate chips
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