Probably when my mom and I walked into the MSICU to see my dad completely brain dead. The worst part was when we had to call my grandma to fly down from Maine, and when she stood there holding his hand. But, we already knew it was coming because he's been a drunk since he was a teenager, and started smoking soon after. He was also a drug addict, and he was recently diagnosed with cancer. But the funny part is that he died of a pulmonary embolism, which wasn't even cancer related. But, I consider myself lucky that we didn't have to see him go through chemotherapy, which he was scheduled to do a couple weeks later. I'm lucky that I still have my mom, cause she's my best friend.
As far as anime goes, I cry at absolutely everything so naturally I have a whole bunch of sad moments.
Ace's death and Merry's funeral in One Piece-
I don't really wanna post any from other animes, cause I'm gonna make myself cry some more xD