Regular already-made chocolate doesn’t work well; it has stuff added to it that makes it not good for molding. Use candy melts which you can buy at Michael’s or a cake/candy making shop. Wilton’s are the most famous but I got some at my local shop that taste even better and are a bit cheaper. Also they come in a lot of colors and a few flavors. Milk, dark, white … and then the colored ones usually taste like vanilla or chocolate, depending on the brand. You can flavor them too, but don’t use regular extracts – you need to use oil, not something with water in it. (These are also sold at cake/candy making shops.) There are video tutorials about filling the lollipop molds too. Good luck!

If you do this make sure to remove the chocolate from the mold before putting it in the freezer or the candies won’t pop out! The chocolate will become discolored if you freeze it for too long. Personally, I wouldn’t freeze them after they’re made because they should hold fine in room temperature if you wrap them tight.