Heat the oven to 350°F. Grease and lightly flour one 9×5-inch loaf pan. Measure and place a piece of parchment paper along the bottom.
In a medium bowl, sift together the flour, baking powder and salt; set aside.
In a large bowl or the bowl of a stand mixer fitted with the paddle attachment, beat sugar and butter until light, fluffy and smooth. Add the vanilla and eggs, beating on high speed for 2 minutes.
Add the flour mixture into the wet ingredients, alternating with milk on low speed, beating just until smooth after each addition.
Divide the batter into two seperate bowls. Try to do this as evenly as possible using a kitchen scale or just a measuring cup. Cover and place one of the bowls of batter into the refrigerator.
In the other bowl, add the raspberry extract and red or pink food coloring, blend until fully mixed and transfer to the prepared loaf pan.
Bake for 50-60 minutes or until it passes the toothpick test. Remove the from the oven and allow to cool fully before inverting onto a cutting board.
Measure the depth of your cookie cutter (preferably 1 1/2 inches tall). Cut cake into slices equal to the depth of your cookie cutter. Cut each slice and place cut-outs into an airtight plastic bag. Freeze for a minimum of 2 hours.
When you are ready to make the rest of the cake, preheat the oven to 350°F again and prepare the same loaf pan with cooking spray, flour and parchment paper along the bottom.
Spread some of the batter into the bottom of the loaf pan and then stick the frozen hearts together down the center. Spoon the remaining batter over the cut outs, letting it drip down the sides. Using a knife or spoon, spread so it isn't too thick over the top.
Bake for another 55-60 minutes. If it starts to brown, but is not passing the toothpick test, loosely cover with a leaf of aluminum foil.
Remove from oven and allow to cool. Run a butter knife around the edges and then place onto a cooling rack until fully cooled.
Blend together the cream cheese and butter. Add the vanilla extract and 2 cups of the powdered sugar.
Add the whole raspberries and continue to blend until they are pureed into the frosting. Depending on the water content of the fruit, you may need to add more powdered sugar to get a drizzle-able consistency.
Spoon over the top of the cooled cake and serve!
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