I would have to definitely say, watching WM on PPV when Michaels retired Flair. I was watching the PPV with my girlfriend at the time, who loved WWE, and her parents came into the room. Now, everyone else didn't truly understand the history and contributions Flair has put in to the wrestling business, but I did. So when I saw Michaels say he loved him and he was sorry, executing the 2nd super kick, and then realizing it was it for Flair, was tough! lol I felt like such a girl but I had the biggest knot in my throat and I wanted to cry! but, of course, due to the circumstances I was facing, I obviously could not do that. Had I been in a room by myself, it would have been a different story!
I just remember how utter sad it was, knowing Flair had given his life to the business, looking so beat up and just physically fatigued, barely able to stand on his fragile knees, already crying a bit, motioning for Shawn to kick him one more time, was heart wrenching to say the least!
Flair is back though now, which puts a damper on the moment a tad, but it's still the saddest I remember being in wrestling, story-line wise!