Preheat the oven to 350 degrees F. Line two baking sheets with parchment paper. Place the lollipops 2 inches from the edge of the pan and 4 inches apart.
Mix the cookie dough with the flour until it is an even texture. Use a round teaspoon measuring spoon to form leveled half circles. Use your finger to gently ease the dough out of the spoon. Place 5 of the half circles, rounded-side up, around each lollipop, leaving a little space so that they are not quite touching.
Bake the cookies, rotating the pans top to bottom and front to back midway through baking, until the candy melts and the cookies are slightly puffed and just golden, 12 to 14 minutes. Let cool on the pans until the candy hardens, about 10 minutes.