So one of my best friends from high school was going through a rough, ROUGH time...without getting too much into it, his step dad attacked his mother with a baseball bat, and she was doing very badly in the hospital...
I and many other friends were at his aunts house, where he was, as moral support and to be there for him while his mother was in critical condition...you have to understand the scale of the injuries that my friend wasn't allowed to be at the hospital, we were all Juniors in high school...
One of his relatives, it might've been his aunt, returned home, and at that time I remember our crew was around the friend who was sitting in the center of the room. His aunt handed him a plastic bag with a biohazard symbol in it, some sort of a cloth inside, and I decided to crack the joke, "Hey, awesome! Radioactive pajamas!"
The room was dead silent as they solemnly watched my friend. His aunt placed a hand on his shoulder, and he bent over in his chair, and hugged the bag, and pressed it against his face...then it hit me...they had pulled the plug, and thats what she was wearing...packaged in whatever they had laying around the hospital for my friend to keep.
I recoiled inside at such depths, that if I had died at that moment, I would've been perfectly fine with that...it was such a heart tightening cringe, that it serves as a MASSIVE reminder about the whole "there's a time and a place for everything" mentality, ESPECIALLY when it comes to jokes...he's still my friend, he knows I'm a dork and a clown...but that's definitely top 10 cringiest shit I've ever done. The shame is deep.