After heavy testing, it appears that this is a timing glitch. I'm not too sure of what's going on in the background but I can guess from the behavior that some GL object are not ready when attempting to display the dialog cause the dialogs not to be drawn.
I found a workaround by just declaring a handler in the class and doing a post event to the handler to show the dialog. It seems to give the activity enough time to intialize everything and the problem no longer occurs.