Let me dissect the post
If both opponents were to fight each other with raw skill, considering Sayori isn’t self aware, Sephiroth would win. If Sayori was self aware, depending on whether sephiroth.chr was an existent entity, she could either win or, in the worst possible case scenario at least for Sayori, it could end in a tie. However, this is taking into consideration how Sephiroth’s backstory would affect his opinion on Sayori. A cliche trope seen in some fictional series or even fanfics is the idea of a dangerous villain and the kind and gentle sweetie becoming the best of friends. As wholesome as it is, it is a little too generic and shallow, and would need a little more depth, which “Sayori and Sephiroth” actually has (hmm yes the Sayori and Sephiroth iceberg). As evil as Sephiroth may seem, he still has his own traumatic backstory which makes him a little more human than villains who are just pure evil and can never be redeemed. Because he has a facet of him that is conventionally “human”, it would make sense that despite being evil, even he can’t resist the wholesomeness and adorableness of Sayori, who herself has struggled a lot due to her trying to make sure everyone was happy while being unable to be happy herself due to her depression kicking in. Even if Sephiroth is the type of person who would wholeheartedly commit genocide, he still wouldn’t bring himself to kill, or generally yet, harm Sayori. Rather, he would want to hug her and be able to be there for her, as well as having someone who could console him when needed.
TL;DR: If both characters were to use their raw strength, Sephiroth would win. But since we are taking psychological setbacks into consideration, Sayori would ultimately win the faceoff
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