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1
Position rack in the center of the oven; preheat oven to 350; line a baking sheet with parchment paper; set aside.
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2
Add chocolate to the top of a double boiler set over about 1 inch of simmering water, placed over medium-high heat.
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3
Stir with a heat-safe rubber spatula or wooden spoon until half the chocolate has melted, then remove the top part of the double boiler; continue stirring until all the chocolate has melted; set aside to cool for 5 minutes.
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4
In a mixing bowl, whisk the flour, baking soda, and salt until uniform; set aside.
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5
In another bowl, beat the butter and shortening, using an electric mixer at medium speed, until softened and smooth (about 1 minute).
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6
Add in brown sugar and sugar; continue beating about 2 more minutes, until pale brown, thick, but still somewhat grainy.
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7
Beat in egg and vanilla, then pour in chocolate all at once and beat until smooth, about 1 minute.
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8
Using a wooden spoon/spatula, stir in the flour mixture just until you can see no white streaks in the batter; stir in the milk until moderately smooth, then stir in the remainder of the flour just until uniformthere may still be small lumps in the soft, wet batter.
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9
Drop by heaping tablespoonfuls onto baking sheet, keep 2-inches apart.
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10
Bake for 16 minutes, rotating sheet once during baking.
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11
When done, the cookies will have rounded, bumpy tops.
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12
Remove baking sheet form oven and press the cookies lightly with a spatula, flattening them at tad to create smoother, rounded tops.
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13
Cool 2 minutes on the baking sheet; transfer cookies to wire rack to cool completely.
