What is the maximum number of intersection points between a quadrilateral and a pentagon, both non-intersecting?
I believe the maximum is 16 as shown below, but I have no idea how to prove this.
Any help or pointers would be greatly appreciated. (Or a diagram with more than 16 intersection points.)

$16$ is the maximum if one proves that a line cannot meet the boundary of a $(2n+1)$-gon at more than $2n$ points. And this is a consequence of the Jordan curve theorem: each time we cross the boundary of a polygon we go from the exterior to the interior or the opposite. If we start at the exterior and we end at the exterior, we have an even number of crossings.