If the chocolate is at the correct temperature, it will take only one dip to evenly coat a balloon. If the chocolate is too cold, then the coating will be too thick; too hot, and the balloon will likely need more than one dip. Keep leftover chocolate to fill any holes in the cups.
Line a baking sheet with parchment paper or a silicone liner. Inflate to about 5 inches in diameter:
Temper and pour into a medium bowl:
Dip the bottom third to half of one balloon into the chocolate, moving it from side to side to coat evenly. Lift the balloon and allow the excess chocolate to drip off, then place, dipped end down, on the prepared baking sheet. Repeat with remaining balloons and chocolate. Refrigerate until set, about 30 minutes. Prick each balloon with a pin to release the air and gently peel the deflated balloon from the chocolate cup. Holes can be patched with the remaining chocolate. Return the bowls to the refrigerator until ready to serve.