As a Grim Reaper, death is no stranger to Grim. It's as natural as breathing for him. Has this made it hard for him to grow attached to people, knowing that death is inevitable? That he is the thing that cannot be prevented? And for those he does care for, is there any sadness or anxiety knowing he'll outlive them or guide them to their final resting place?
death has always been a part of grim's life, but he's never felt a full scope of it until he was older.
when he was young, grim never really thought about it as much because the people within his closest proximity (his mom mostly) would never die. even with his dad being dead, grim never felt the full weight of actually losing a loved one to death. he saw his mom deal with the grief, but she's always been composed and at peace with it, maybe because she anticipated the loss.
it wasn't until he officially became the grim reaper that he started to understand the effect death has on people, and how grief is never as tragically beautiful as the way his mom carried herself. it's ugly, it's raw, it hurts.
grim always tries compartmentalising and, for the most part, he could do it well, but when he sees people being really affected by a particular death, he does have knee jerk reactions. he has compassion for those people, but he also had to keep his distance because he has a job to do—and he knows that he's probably the best person who can help these people navigate death.
the full weight of death only occurred to him once he actually became friends with billy and mandy. they annoy him, sure, but they are probably the closest thing grim has to family (don't let them know that). the only reason he willingly accepted hades' proposition to reap souls prematurely is because he doesn't want them to get hurt or killed, because he also doesn't want to deal with the emotions from losing them. it even surprised him just how much the thought of something happening to them made him sick.
and he's thankful that they're young, so it'll be a while before they would ever face death (provided they take care of themselves), but not going to lie, grim does get upset whenever either billy or mandy celebrate their birthdays.