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1
Sift the flour, baking powder, and salt together in a bowl; set aside.
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2
Beat the 1 cup butter with the sugar, egg, milk, and vanilla extract in another bowl until well mixed.
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3
Gradually mix the flour mixture into the butter mixture.
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4
Shape the dough into a disk; wrap with plastic wrap and refrigerate for at least 2 hours.
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5
Working with half the dough at a time, roll out dough to about 1/8-inch thick.
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6
Cut into cookies with a large heart shaped cookie cutter. Repeat with the remaining half of the dough.
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7
Cut the center of half of the cookies with a smaller heart shaped cookie cutter.
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8
Place an open centered cookie on top of a whole cookie to form a sandwich. Arrange cookies on an ungreased baking sheet; set aside.
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9
Preheat an oven to 400 degrees F (200 degrees C).
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10
Place the raspberry jam in a microwave save bowl and heat on high until jam is runny, about 35 seconds.
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11
Fill the center of the cookies with the jam. Refrigerate cookies for 10 minutes.
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12
Bake in the preheated oven until the cookies are firm to the touch, 5 to 8 minutes. Cookies will be pale in color.
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13
Transfer cookies to a wire rack to cool completely.
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14
Melt the chocolate and 2 tablespoons butter in a microwave-safe glass or ceramic bowl in 30-second intervals, stirring after each melting until smooth, for 1 to 3 minutes, depending on your microwave.
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15
Spoon chocolate decoratively over half of each cookie.
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16
Place cookie on a waxed paper lined baking sheet and refrigerate until the chocolate has set, about 15 minutes.
