Line 1 (or 2) cookie sheets with parchment paper (or aluminum foil lined with butter) and spread around 1/2 of the melted chocolate on each, separately, about 0.2 cm thick.
Place the trays in the freezer for 2.5 min.
Using the cookie cutter, press gently into the chocolate like you would cookie dough. But do not remove the pieces yet. Make sure you have 12 clouds from each type of chocolate (24 all together).
Place the tray back into the freezer for an additional 2 minutes and gently peel off. Store clouds either in the fridge or at room temp.
Place the remaining chocolate in 2 separate piping bags either with a small hole snipped off (like 0.1 cm in diameter) or using a #1 or #2 piping tip.
Flip the clouds so that the bottom side is up (the smoother side) and pipe your desired message on each. I’d go with “Okay?” on the dark one and “Okay.” on the white one. Holding the piping bag like a pencil is easier when working with chocolate- make sure that the top is sealed properly with a rubber band or clamp though. Place back into the freezer for 2.5 more minutes to set.
Place a dollop of frosting on top of each cupcake and smooth out. Dip the cupcake head first into the blue sugar until coated.
Place the dark cloud on the top center of the cupcake, make sure to add a little extra frosting on the back so that it sticks.
Place the white cloud so that it very slightly overlaps the dark cloud at the bottom center. Done.