Pulse the yogurt, cream cheese, milk and vanilla, and sweetener of your choice in a blender or food processor until combined and smooth. Test/adjust sweetness. Pour one cup of the mixture into a medium sized bowl and whisk in the cocoa. 

Spoon the mixtures into the popsicle molds. as you like. You can make some of the plain vanilla mixture and then a little chocolate or vice versa. Add 3-4 cherry halves to each mold. Place the cover on and sticks inside and freeze 6 hours or overnight. When ready to serve. run the molds under hot water for about 20 seconds or leave them out at room temperature for about 5 minutes to make it easier to remove them. 

Melt the dark chocolate and coconut oil or shortening (if using). Dip the popsicles in the melted chocolate or drizzle them with chocolate. Freeze a few minutes until chocolate hardens then enjoy!