Special equipment: 2 1/4-inch round cookie cutter, 1 1/2-by-1-inch heart-shaped cookie cutter
Prepare dough as directed and chill for 2 hours.
Preheat the oven to 375 degrees F.
Sprinkle a work surface and rolling pin with confectioner's sugar and roll out dough to 1/8-inch thick. Move dough frequently to prevent it from sticking and add more confectioner's sugar to the work surface and rolling pin as needed. With a 2 1/4-inch round cookie cutter, cut 72 dough rounds, re-rolling dough as needed. With a small heart-shaped cookie cutter (about 1 1/2-by-1-inch), cut hearts from the center of half the dough rounds. Place the rounds and cutouts about 1 inch apart on parchment -lined baking sheets. Bake until just set but not brown, about 6-8 minutes. Let cool on the pan slightly before transferring to a rack to cool completely.
Meanwhile, make the filling: In a small bowl, whisk together the cream cheese, butter, confectioner's sugar, and pomegranate juice until smooth and fluffy. Spread about 1 teaspoon filling on each round cookie and top with a cut-out cookie. Place a red candy heart in the center of each. Leftover filling can be used to sandwich the small hearts together.
Sift together flour, baking powder, and salt. Set aside. Place butter and sugar in large bowl of electric stand mixer and beat until light in color. Add egg and milk and beat to combine. Put mixer on low speed, gradually add flour, and beat until mixture pulls away from the side of the bowl. Divide the dough in half, wrap in waxed paper, and refrigerate for 2 hours.
Preheat oven to 375 degrees F.
Sprinkle surface where you will roll out dough with powdered sugar. Remove 1 wrapped pack of dough from refrigerator at a time, sprinkle rolling pin with powdered sugar, and roll out dough to 1/4-inch thick. Move the dough around and check underneath frequently to make sure it is not sticking. If dough has warmed during rolling, place cold cookie sheet on top for 10 minutes to chill. Cut into desired shape, place at least 1-inch apart on greased baking sheet, parchment, or silicone baking mat, and bake for 7 to 9 minutes or until cookies are just beginning to turn brown around the edges, rotating cookie sheet halfway through baking time. Let sit on baking sheet for 2 minutes after removal from oven and then move to complete cooling on wire rack. Serve as is or ice as desired. Store in airtight container for up to 1 week.
Recipe courtesy of Alton Brown