In a food processor or high powered blender combine the cashews, coconut milk, coconut oil, cocoa powder, dates and vanilla extract. Blend until smooth, thick and very creamy, about 10 minutes. Scape down the sides of the bowl 2-3 times during blending.

Spray six popsicles molds with cooking spray or olive oil spray. Divide the mixture among 6 popsicle molds or I highly recommend using small paper dixie cups. I used the molds the first time I made these and they were pretty hard to get out. The second time I used paper cups and just peeled the paper away. It worked much better.

Freeze the popsicles overnight.

Once the popsicles are frozen make the chocolate shell. Combine chopped chocolate and coconut oil in a medium sauce pan over medium heat. Stir frequently until chocolate is almost melted. Remove from heat and stir until completely melted and smooth. You can also do this in the microwave.

Remove the popsicles from the freezer and peel away the paper cups (or remove them form the molds). Dip each popsicle in the chocolate shell sauce and then place on a wax or parchment paper lined baking sheet. Repeat with the remaining popsicles and then place the pan in the freezer for at least 10 minutes. Keep frozen.