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Cut the pound cakes in half horizontally and lay the halves flat. Using a 3-inch heart-shaped cookie cutter, cut out 3 hearts from each half. (Tip: reserve the scraps for a layered dessert.)
Spread the top of the cupcakes with some of the vanilla frosting. Place a pound cake heart on top of each cupcake, pressing down to secure. Place the cupcakes in the freezer for 15 minutes, or until slightly frozen.
Tint 1/2 cup of the vanilla frosting red with the food coloring. Spoon the red frosting into a ziplock bag, press out the excess air, seal, and set aside. Divide the remaining frosting among five small microwavable bowls. Tint each bowl a different pastel color of pink, green, yellow, orange, and lavender. Cover with plastic wrap and set aside.
Working with one color of frosting at a time, microwave the frosting, stopping to stir frequently, until it has the texture of lightly whipped cream, about 10 seconds. Remove 1 cupcake at a time from the freezer. Holding the cupcake by its paper bottom, dip it into the frosting just to cover the pound cake heart. Allow the excess frosting to drip off back into the bowl (see page 15). Turn right side up and let stand. Repeat with each color and the remaining cupcakes. If the frosting becomes too thick, reheat for several seconds, stirring well. Remove any excess frosting from the base of the hearts if necessary.
Snip a very small (1/16-inch) corner from the bag with the red frosting. Pipe sayings on top of the hearts. Place on a serving platter. Sprinkle the conversation heart candies around the platter at the base of the cupcakes.