Separate out 4-6 cherries for decoration, then set them aside.
For the remaining cherries, remove stems and cut them into 1/2 or 1/4. In a small bowl, add the chopped cherries. Spray some whipped cream into the bowl, then mix well. Feel free to add as much cream as you like, but be sure to mix it well so it isn't too fluffy. Set bowl nearby.
Stop mixer and dark chocolate cake mix, powdered sugar, and milk to bowl. Begin to mix again, starting out on low speed and gradually increasing to medium-high. Mix until dry ingredients are fully incorporated with the rest, about 5-7 minutes. Set dip aside.
To serve dip: Add about 1/2 of the dark chocolate cake dip into a serving bowl of your choice. Create a small well in the top of the dip. Next, add the creamy cherry mix to the bowl, filling the well. Top the cherry mix with the remaining dark chocolate cake dip, smoothing out the top. Spray more whipped cream on top of the dip and then decorate with the stemmed cherries.
Serve dip immediately with cookies for dipping.
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