21. Let Him Read
An employee of mine drunkenly sent d*ck pics, in the middle of the night, to my boss and multiple other associates.
I had to deliver the termination because she, my boss, was directly affected and I was uninvolved in the incident. When he asked why I just slid the termination document across the desk and let him read the described events as written for his HR file.
Even better, he was a former high school friend of mine. I had helped him interview for a lesser role many years prior.