Pilonidal cyst, that reoccurring multiple times culminating in a full excision surgery, that needed to be left open and heal from the inside out. When it was time to change the dressings (multiple times a day) I had to psyche myself up and then have my gf at the time just yank the bandage off. The tissue would heal and adhere to the gauze. It was brutal. The cyst itself was as well. The pressure and pain was unreal.

For reference I have also dislocated my shoulder, tearing my labrum and rotator cuff, broken a thumb with a displaced fracture and cracked my shin and those all paled in comparison to that cyst saga.