like pulling teeth

Said of something that is especially difficult, tedious, requires an extreme amount of effort, or is done in the most difficult or unpleasant way possible. With this new way of preparing vegetables, you'll no longer have to pull teeth to get your kids to eat their greens! I've been pulling teeth trying to get my family members organized for this get together, but I think it will all be worth it!

like pulling teeth

Very difficult, especially to extract information from someone. For example, It's like pulling teeth to get a straight answer from him.

like pulling teeth

If doing something is like pulling teeth, it is very difficult. Identifying poor working practices is easy. Doing something about it is like pulling teeth. Trying to get him to talk about his music 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 anaesthetic and so it was difficult and painful.