like pulling teeth

used to refer to something that is inexplicably difficult

The idiom "like pulling teeth" is used to describe a task or process that is extremely difficult, frustrating, or slow. The expression draws its metaphorical meaning from the challenging and often painful process of extracting teeth, which requires significant effort, precision, and patience. When something is compared to pulling teeth, it suggests that it is arduous, requires great persistence, or encounters resistance.

Convincing him to try a new hobby was like pulling teeth.He was resistant to change and reluctant to step out of his comfort zone.
Getting a straight answer from the evasive witness during the interrogation was like pulling teeth.The information was extracted slowly and with great effort.
Trying to gather accurate data for the research project was like pulling teeth.The participants were uncooperative, and the process was time-consuming and frustrating.
Getting my teenage son to clean his room is like pulling teeth.He procrastinates and resists every step of the way.
Persuading him to lift the charges was a challenge, like pulling teeth.I don't want to ever go through that again.