* Curly hair: Often seen as unruly and difficult to manage.
* Curly lines: In written language, a "curly" line might signify a twist or unexpected change in direction, making something more complicated to follow.
* Curly wood: Curly wood grain is intricate and difficult to work with.
Therefore, a "curly question" is simply a way of describing a question that is difficult to answer, perhaps requiring a lot of thought or explanation. It's likely the idiom evolved through everyday speech and became popular due to its descriptive and relatable nature.