Preheat your oven to 350°F. While it heats, sift together the powdered sugar, flour, baking powder, and salt in a medium bowl to remove any lumps and ensure even distribution—this is crucial for tender cookies. Have your egg at room temperature (around 70°F) and cut the butter into tablespoon-sized pieces for faster, more even beating. This prep work takes just a few minutes but makes the mixing stage much smoother.

Using an electric mixer on medium speed, beat the butter for 2-3 minutes until it's light and fluffy—this incorporates air that helps create tender cookies. Add the 1/2 cup sugar gradually and beat for another 2 minutes until pale and creamy. Add the room-temperature egg and vanilla extract, beating until fully incorporated. Reduce speed to low and add the dry ingredient mixture from Step 1, mixing just until the dough comes together into a cohesive ball. I like using Kerrygold butter because it gives the cookies a richer, almost caramel-like flavor that pairs beautifully with the jam.

Divide the dough in half. Roll the first half between two pieces of parchment paper to 1/8-inch thickness, then cut out solid heart shapes using a small heart cutter. Place these on a parchment-lined baking sheet. Roll the second half to the same thickness and cut out larger heart shapes using a large heart cutter. Using a smaller heart cutter, carefully cut out the center of each large heart to create a frame shape, then place these on a separate parchment-lined baking sheet. This two-cutter technique creates the window effect where the jam will show through.

Place the solid hearts in the preheated oven and bake for 10 minutes until just set but still pale—they should not brown much. Simultaneously, bake the heart frames on the separate baking sheet for 8-10 minutes until the edges are lightly golden. Both batches should cool completely on the baking sheets for 5 minutes, then transfer to a wire rack to cool fully. This staggered baking time accounts for the different thickness of the two shapes.

Once both cookie types are completely cool, spread about 1 tablespoon of raspberry jam onto the flat side of each solid heart cookie. Top each jam-covered cookie with a heart frame cookie (jam side down), pressing gently so the jam fills the window cutout. I always use Bonne Maman jam because it has the right balance of fruitiness and sets nicely without being too thick or too thin.

Using paper heart cutouts as stencils, place one centered over each cookie sandwich to protect the jam window. Dust the entire cookie surface generously with the 1/4 cup powdered sugar, then carefully lift away the paper stencils to reveal the framed jam centers with a beautiful powdered sugar border. The contrast of the white powdered sugar framing the ruby-red jam creates the perfect Valentine's Day presentation.