The problem is that RelativeSource does not work in the following case. I use silverlight 5.
//From MainPage.xaml
Popups are not part of the visual tree.
Relative Source "Gets or sets the binding source by specifying its location relative to the position of the binding target (MSDN)". Since Popups are not part of the visual tree of the control that is showing it, it will not be able to resolve anything outside of the popup.