Preheat oven to 350 degrees F. Line 2 muffin tins with about 18 paper liners. Set aside.
Prepare the chocolate and vanilla cake mixes in separate bowls using the ingredients and directions on the back of the boxes. Stir the vanilla pudding mix (the dry mix) into the vanilla cake batter, and stir the chocolate pudding mix into the chocolate cake batter. Allow the batters to set for about 5 minutes until thickened.
Working quickly with two separate cookie dough scoops or spoons, spoon about a heaping Tablespoonful of batter onto the left side of the cupcake liner with one flavor. Then immediately spoon the other flavor onto the right side of the cupcake liner. Repeat layers, filling the cupcake liners about 3/4 full. You should have roughly around 18 cupcakes, maybe a couple more depending on the box mixes.
Bake for approx. 15-18 minutes or until a toothpick inserted near the center comes out mostly clean or with moist crumbs. Cool completely.
While cupcakes cool, make your frosting: In the bowl of a stand mixer, cream together the butter, strawberry jam, vanilla, strawberry extract and milk with the paddle attachment for about 2 minutes or until creamy. Add in the powdered sugar, about a cup at a time, until a light and fluffy texture has been achieved. Add in food coloring, only a couple drops at a time, and beat until a light desired pink shade has been achieved.
Spoon the frosting into the piping bag attached with an open star tip. Pipe high onto cooled cupcakes and immediately garnish with white non-pareils sprinkles and a cherry. Serve immediately or store leftovers airtight in the fridge.
*NOTE: If you want to pipe the frosting thick onto the cupcakes, consider doubling or tripling the recipe.*