That's Brown from
Rule of Rose.
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Do not look up Brown from
Rule of Rose.
But to answer your question, no, not even remotely sorry about Sif. I'm sorry when I kill the colossi in Shadow of the Colossus, and the buffalo in RDR, and the elephant in It Takes Two, and basically any game that wants me to harm anything that's minding its own business, including
Maiden Astraea in Demon's Souls. Sif is just one more thing that pops out of nowhere, without any context, and tries to kill you, for no clear reason and to no evident effect. If Hidetaka wanted me to feel anything for sword pupper he should've given me a story, not lore tucked at the bottom of DLC. I did feel a bit sorry when I noticed, rewatching the clip, that the dog had started limping.
Then there's stuff like the dogs in The Last of Us, where the sadness at murdering them (in self-defense) is overshadowed by the relief at not having to deal with their bullshit while trying to maintain stealth. When I'm fighting Sif I'm dreading the run back from the bonfire, not the moral implications.
In other news, I managed to ace Pinwheel in one go too. I imagine nobody's going to care for that creep.
And holy bejesus I swear I have a single HP left at one point.
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Thankfully Vitality wins the fight, which lasts less time than the intro cutscene for the boss.