Preheat oven to 375 degrees F. Line baking sheets with parchment paper.
Sift dry ingredients in a mixing bowl.
In a separate bowl, beat softened butter and brown sugar until fully combined and butter appears light and airy (approximately four minutes). Add the egg and vanilla and beat until just incorporated.
Alternately and with beaters on, add flour mixture and milk until all ingredients are just combined. Do not overbeat.
Drop batter in rounds on parchment paper; bake for 10 minutes or until done. Remove from oven and cool.
Pour whipping cream into clean mixing bowl; sprinkle gelatin over top and let sit for two minutes. With clean beaters, mix whipping cream, gelatin, and superfine sugar until soft peaks form.
Place dollop of whipped cream between two chocolate whoopie cookies. Sprinkle pomegranate seeds on the sides and top; serve.