It was my first Valentine's Day where I thought I would be crafty for the kids classrooms. I followed a tutorial that I can't find anymore but similar to this blog post. The first turned out OK but towards the end they were pretty near perfect! Once I got the hang of it, it became easy. Here is the tutorial that I followed over at How Does She?
I found that if you opened the cookies (I used Double Stuf) when you pressed in the stick if you turned the stick while pressingyou had less breakage. Also when dipping I held the cookie with the stick going straight up and spooned the chocolate over it. Then using a slotted spoon I scooped it up and tapped the spoon on the side of the dish to get off the extra chocolate. Then I was able to push the oreo off dragging the bottom along the side of the spoon onto the wax paper. The tapping created a nice smoothe finish on the top.
Then for our primary kids at church I made Sugar cookie pops using some friend's pans. You can see the pans here.