A: How was your date?

B: I don’t know. I like the guy, but trying to get him to talk about himself and his family was like pulling teeth.

Note: When a dentist pulls someone’s tooth, they pull it out of their gum. In the past, this was done without anesthetic and so it was difficult and painful. This idiom is used to describe something that is especially difficult, tedious, requires an extreme amount of effort, or is done in the most difficult or unpleasant way possible. For example: Identifying poor working practices is easy. Doing something about it is like pulling teeth.