what is " Like pulling teeth " ?
"Getting him to talk about his job was like pulling teeth!"

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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

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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.

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like pulling teeth= a difficult task

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something to hard do

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It means extremely difficult

cowboy...