Pour popcorn into a large bowl and remove any leftover unpopped kernels.
In a medium-sized microwaveable bowl, melt the chocolate chips and peanut butter in the microwave, cooking for 30 second intervals and stirring after each interval until the chocolate and peanut butter combination is completely smooth (mine was completely melted after 90 seconds, but it will depend on your microwave). Be careful not to burn your chocolate. Stir in the vanilla extract.
Pour over the popcorn and carefully stir to distribute the chocolate evenly. Make sure each popcorn is completely covered. (This may take awhile, but it will eventually even out.)
Pour into a large gallon sized ziploc bag or resealable bag. Pour powdered sugar into the bag, seal it, and shake until all the popcorn is covered in powdered sugar.
Pour into a large bowl and enjoy! Store leftovers in an airtight container or resealable bag for 2-3 days…if it even lasts that long. :]