For the cupcakes:
For the vanilla buttercream frosting:
For the filling:
Preheat oven to 350℉. Line a standard 12-cup muffin tin with paper liners.
In a bowl, whisk to combine flour, cocoa powder, baking powder, baking soda, and salt. In a separate bowl whisk together eggs, sugar, oil, milk, and vanilla. Add milk mixture to the flour mixture and stir just until batter is smooth. Fold in chocolate chips.
Divide batter evenly amongst lined muffin cups, filling to about ¾ full. Bake for 15-20 minutes or until a toothpick inserted in the center comes out clean. Let cupcakes cool in pan for 10 minutes, then transfer to a wire rack to cool completely.
In a medium bowl or stand mixer beat butter and powdered sugar until smooth, about 2-3 minutes. Beat in vanilla and milk until light and fluffy, scraping down the sides of the bowl as needed.
With a small heart-shaped cookie cutter or sharp paring knife, cut a small ½” deep heart-shaped hole from the center of each cupcake. Ice the edges of each cupcake then fill the heart centers with cherry preserves.