Every part of the Witcher

When Sarah died in the Walking Dead: Season 2.

"Good. That's one less loose end."

Finishing the Fight.

Arthurs death in RDR2 and the final ride before hits hard

When Vito and joe killed Tommy

Getting to the end of Night in the Woods.
Never had post-game depression harder than then.

Failing to save Solaire in Dark Souls

In the original last of us, with the brothers.

Watching Thane Krios die of space cancer or watching Legion give himself up for the Geth

Gears 5, when I saved JD and Del died. Reuniting with the rest of the group and telling them of his fate hurt, especially to Fahz.