Hi, your question is not dumb... when I cover my cookies w/ Fondant I don't measure because I use the same cookies cutter to cut the Fondant.. like here: These cookies I made were about 4 inches wide and I made 4 dozens of them. I made about 3 batches of MMF. Show us a photo of your cookies later.
I used about 2 1/2 lbs of choco-pan fondant to cover 60 cookies. I did some the other day and to do a batch of no fails it probably would have needed 2-3 batches of MMF. HTH