In my previous adventure I rolled out a male Grizzly Bear brawler named Tunrik. Finding that the Lady of the hamlet was less then knowledge I sought after the elven spearwoman Nisa Leadredsea for directions. Seeing as she was an experienced adventurer He asked her to join him. It turns out the two of them worked together magnificently, steamrolling through though most of the bandits of the northern half of the continent. Nisa had a penchant for surviving serious wounds, emerging from several different head, arm and leg trauma with little less then small scars. Having slaughtered all that I felt comfortable slaughtering in the north, we began the long trek to the other end of the island continent in search of several megabeast lairs rumored to be found there. Along the way they slayed wild animals, bandits, gained a new companion, another spearwoman by the name of Orsuma, defended towns against goblin raiders and looted an exceptionally large amount of waterskins.
It is here were the regret starts. Orsuma was slain, and Nisa was heavily injured by a lasher during the trio's defense of a human hamlet. Enraged by the harm that came to his friends, Tunrik mauled the remaining raiders, inflicting an agonizing death to each of them. From this point forward Tunrik made a point to slaughter every goblin he came across. The pair remain in the hamlet for a week to recuperate (i.e. Nisa bugged out and disappeared and I retired and returned back to the character to fix it.) As the two left to continue their journey, Nisa shared her views on loyalty, on how one should never get close to other people, because then it will hurt when they die. (No joke she actually did this, I love when the random conversation seem like they have a meaning) Shocked by this statement, the loyal Tunrik argued to value of putting trust and loyalty in companions. This argument was met with derision, and when pressed about it she was only able to respond with a a confused "I don't know". Unwilling to press it further Tunrik dropped the argument, but became determined to prove her wrong, to show her that he would never fail her.
The two continued onward, continuing to fight and kill until a fateful encounter with a giant wolf and the beginning of the end. With a snap of its jaw Nisa's severed foot flew in an arc, crippling her. However Tunrik drew its attention with a devastating punch to the gut. Taking advantage of the distraction, Nisa crawled to the wolf and jammed her spear up into its head, shattering the skull and knocking the great beast unconscious, ripe to be killed by Tunrik's Stomp of Doom. Things continued to get worse as their next battle against a giant dingo left Tunrik's right arm completely useless. After barely managing to fight off a pack of (normal sized) dingos, the two cripples decided together it was finally time to retire and began the trek to the nearest hamlet.
But this hamlet was under attack, by none other than goblin raiders. Despite better judgement, Tunrik charged into battle. They had effortless killed many similar attacks, even crippled this one wouldn't be to hard right? However the goblin swordsman Tunrik found first was much more skilled then he realized, and managed to fend him off until a hidden crossbowgoblin landed a shot into his good arm, and then his leg, and then his chest. As he opened his eyes one last time before the swordsgoblin finished him off, he saw the mangled remains of his oldest and greatest friend; bones sticking out at all angles, and teeth ruined beyond recongition. Around her was the remains of a axegoblin, still embeded with her trusty copper spear; a goblin whose face and chest was covered with large seeping bite wounds, who would soon collapse from bloodloss; the shattered remains of her shield, and the cackling hammergoblin who stood over her, his silver hammer red with her blood. His last thoughts were, "I'm sorry Nisa, I failed you. Just like you said I would."
TL;DR My greatest regret is that I killed both one of my favorite adventurers ever, and the person who is easily my favorite companion I've ever had, did it so ignobly, and did it in such a way that she died tragically mirroring her cynical outlook, the one I was determined to change. All because I thought The two could have one last battle.
To be perfectly honest I regret Nisa dying more than Tunrik.