Preheat oven to 350°F. Line a 12-cup muffin pan with paper cupcake liners.
To prepare the cupcakes, sift together both flours, the baking powder, and salt in a medium bowl; set aside.
In a bowl of a stand mixer, fitted with a paddle attachment, cream the butter, sugar, and vanilla extract until smooth. Add the eggs and mix until fully incorporated. Add the dry ingredients to the butter mixture in three batches, alternating with the milk and ending with the dry ingredients. Mix until just combined; do not over beat.
Scoop the batter into the prepared cupcake pan, filling each space about 3/4 full. Bake for 25 to 30 minutes, or until a cake tester inserted into the center of each cupcake comes out clean and they are light golden brown on top.
To prepare the frosting, whisk the cream in a medium bowl until soft peaks form; set aside in the refrigerator. In the bowl of a stand mixer, beat the cream cheese on medium speed until smooth. Add the peanut butter, confectioners sugar, and vanilla and mix until creamy. Pour the whipped cream into the bowl with the peanut butter mixture and mix until light and fluffy. Wrap with plastic and refrigerate until needed.
To fill the cupcakes, cut an inverted cone-shaped piece out from the top-center of each cupcake with a small knife. Trim 3/4 of the cone portion off, reserving just the round base. Fill the cavity of each cupcake with strawberry jam and place the reserved round piece of cut cake into each filled cavity to close it.
Spread or pipe the peanut butter frosting on top of each cupcake. Decorate each cupcake with a quarter-cut piece of strawberry.
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