Like pulling teeth
Definition 1 of 1
Pro Tip 1/3Metaphorical Pain
The phrase suggests an experience that is as unpleasant or difficult as physically pulling out teeth. 
Sitting through that meeting was like pulling teeth.
Pro Tip 2/3Emphasize Frustration
Use it to stress the level of difficulty or resistance encountered in doing something. 
Convincing her to admit the mistake was like pulling teeth.
Pro Tip 3/3Informal Expression
The phrase is informal, so it's best used in casual conversations or informal writing. 
Getting a refund from that shop is like pulling teeth.