In a large bowl with an electric mixer, mix butter until fluffy, add in sugars and mix until well combined, at least one minute. Add in vanilla and milk and mix until very well combined. In a separate bowl, combine salt, flour and baking soda. Mix into butter mixture, along with the 5 Dove Dark Chocolate Promises that have been cut into 9 piece each. Combine until all ingredients are mixed, but do not over mix. Chill dough in refrigerator for at least 30 minutes. You can leave the dough in the fridge overnight if needed, but the dough will start to dry out slightly the longer it's left in the fridge.
After dough has chilled, separate into 12 pieces, and roll each into a small round ball. Return to fridge to chill.
Unwrap 25 Dove Dark Chocolate Promises, and chop pieces (cut each Dove promise into approximately four pieces). Place in a microwave safe bowl (glass works well) and heat in microwave at 50% power for 20 seconds. Remove from microwave and stir well, return to microwave and heat again for 20 seconds at 50% power. Repeat this process until chocolate is mostly melted, then continue stirring to fully melt chocolate.
Line a baking sheet with wax paper. Working one cookie dough pop at a time, dip your lollipop stick into the melted chocolate, covering one end of the stick with about 1" of chocolate, then slip the stick into a cookie dough pop. You are not dipping the entire pop, just the stick, and then placing the chocolate dipped stick into a pop. Once all pops have their sticks, place them in the freezer for 5-10 minutes. This helps the pops stay on the sticks. Remove pops from freezer and working one pop at a time, dip into melted chocolate, covering pop. Hold pop over your bowl to allow excess chocolate to drip off, this usually takes 30-60 seconds, but helps prevent excess chocolate from dripping everywhere. Sprinkle with sprinkles if desired. Place dipped pop onto a wax covered cookie sheet (or into a cake pop stand if you have one). Repeat with all pops. Place in the fridge to chill for at least 30 minutes prior to serving. Store in fridge for up to one week.