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1. Preheat oven to 325 degrees and line a 11 X 13 pan with foil (let some hang over the edge to it's easy to lft the dessert out when finished), then spray or butter the foil.
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2. Brownies: In a microwave proof bowl, melt the chocolate the 30 second increments and stir until smooth. Set aside to let cool.
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3. Cream butter and brown sugar together for 2 minutes.
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4. Add eggs and vanilla extract, scrape the sides of the bowl as necessary.
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5. Pour in chocolate, mix well.
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6. On low, mix in flour just until combined.
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7. Pour into foiled pan and spread evenly.
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8. Bake for 25-30 minutes. (The longer you leave it in, the more "cakey" your brownie layer will be. Less time means a fudgey brownie.)
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9. Let brownies cool completely.
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10. Cook Dough: Beat butter, brown sugar and sugar together for 2 minutes.
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11. Add milk, vanilla and flour and mix just until combined.
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12. Stir in 1 1/4 cup of chocolate chips.
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13. Spread cookie dough onto cooled brownies, then sprinkle the remaining 1/4 cup of chocolate chips on top and gently press in.
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14. Cover and refrigerate for 1-2 hours for easy cutting.