The girl who asked the Boxer/Briefs question was the daughter of a Viacom company journalist. They sat at the kitchen table and discussed what to ask Bill and settled on a question about drug legalization.
The screeners then demanded something more tame ergo the light hearted "Boxers or Briefs" question.
During the primaries, Hilary was asked at a town hall, “Diamonds or Pearls?” I thought she was from Pokemon, but she later said that she was told to ask that, and it wasn’t what she wanted to ask.