Old Fashioned Butter Valentine Cookies Dipped in Chocolate

In a medium bowl, whisk together the sifted flour, baking powder, and salt. Set aside. (5 minutes)

In a large bowl, cream together the 1 cup of softened butter and sugar until light and fluffy. Beat in the egg, milk, and vanilla extract until well combined. (7 minutes)

Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Be careful not to overmix. (5 minutes)

Form the dough into a disk, wrap it tightly in plastic wrap, and refrigerate for at least 2 hours to allow the gluten to relax and the dough to chill thoroughly. (2 hours +)

Once chilled, work with half of the dough at a time, keeping the other half refrigerated. On a lightly floured surface, roll the dough out to about 1/8-inch thickness. (10 minutes)

Use a large heart-shaped cookie cutter to cut out the cookies. Repeat with the remaining dough, re-rolling scraps as needed. (15 minutes)

Use a smaller heart-shaped cookie cutter to cut out the center of half of the cookies. These will be the tops of your sandwich cookies. (10 minutes)

Carefully place an open-centered cookie on top of a whole cookie to form a sandwich. Arrange the cookies on an ungreased baking sheet. (5 minutes)

Preheat your oven to 400 degrees F (200 degrees C). (10 minutes)

Place the raspberry jam in a microwave-safe bowl and heat on high until it is runny and easily spreadable, about 30-45 seconds. (1 minute)

Fill the center of each cookie sandwich with the warmed raspberry jam. Refrigerate the cookies for 10 minutes to help the jam set. (10 minutes +)

Bake in the preheated oven for 5-8 minutes, or until the edges of the cookies are lightly golden and the cookies are firm to the touch. They will be pale in color. (8 minutes)

Transfer the cookies to a wire rack to cool completely. (10 minutes)

While the cookies are cooling, melt the chocolate chips and 2 tablespoons of butter in a microwave-safe glass or ceramic bowl in 30-second intervals, stirring after each interval until smooth and glossy. This should take 1-3 minutes, depending on your microwave. (3 minutes)

Spoon or drizzle the melted chocolate decoratively over half of each cookie. (10 minutes)

Place the chocolate-dipped cookies on a waxed paper-lined baking sheet and refrigerate until the chocolate has set completely, about 15 minutes. (15 minutes +)