like pulling teeth

like pulling teeth (extremely difficult) — очень трудно; не допроситься ( не допросишься); клещами не вытянуть; клещами вытягивать надо
If you say that making someone do something is like pulling teeth, it's very difficult and they don't want to do it. It's hard to get them to agree. Usually, it's a matter of getting information, getting them to provide answers or details.

Example 1: Talking to Jerry is like pulling teeth. He usually gives short responses to my questions, and I get the feeling he doesn't really want to share anything personal with anyone at work. (JenniferEFL)

Example 2: Getting her to tell me about her childhood was like pulling teeth. (CID)

Example 3: Getting our kids dressed and off to school in winter is like pulling teeth. (thefreedictionary.com)

Example 4: You know what? It’s like pulling teeth to get you to tell us what you actually want to do. You ever notice that?