If something if like pulling teeth, it is very difficult, especially if trying to extract information or to get a straight answer from someone. http://www.usingenglish.com/reference/idioms/like+pulling+teeth.html

it means painful and very unpleasant... in this sentense it can also mean that the coversation was not easy going, and the asking person had to "pull" the words out.

like pulling teeth= a difficult task

something to hard do

It means extremely difficult cowboy...