For Alice and Angra, it's for them both being misanthropes and being "cursed" to stand apart from human society (with Alice's Witch lineage and Angra being brutalized by his village). It's mostly because it's funny to pair Alice with a Servant that's weaker than her and one that would get on her nerves.
I think Angra is also a good pick for Noel, but I preferred him with Alice. Noel got Cursed Arm because I wonder if he'd just go along with her as did he with Zouken because following his Master is just what he would do at the end of the day, and she seems like she'd really enjoy ordering a Servant around.
For Mitsuzuri, it's a known fact she gets along with Cú in hollow ataraxia and I've thought Robin Hood or Saito Hajime also suit her tastes, but Dumas would make for a funny dynamic. It'd be cool if he makes her a Servant-tier bow (archery is her whole thing) too the same way he made weapons for the Snowfield cops.
For Arjuna and Bazett, I think they gradually could peel off each other's proverbial masks that are major parts of their characters.
For Azaka and Lancelot, it's the idea of forbidden loves (and a Berserker is most fitting for her). For Fujino and Pale Rider, what makes me link them together is "disease" and "death". Considering Fujino starts to enjoy killing with her unlocked Mystic Eyes during her revenge quest, having Pale Rider go along with her whims just as with Tsubaki would make for a very scary combo. I've never played Extra, but from what I get, the Buddha shows up for the bad guy in that plot out of pity for his anguished soul, which I think would also fit for Araya.
Pairing Zealot with someone like Sono-G means she wouldn't immediately kill him because he isn't a Mage and wouldn't have any clue about a Grail is, so you can go lots of places from there. I really love imagining how stumped she would be (like Aoko) at how casually he'd ask her things about herself and his earnestness in general. I also think they're both straightforward and good-natured people that just go for it.
I picked Hippolyta as a Rider for Shinji that wouldn't go along with his orders the way Medusa does (even though she does it for Sakura's sake) because she's too proud and too righteous to ever play along and would result in him getting confronted on how pathetic he actually is.
I haven't gotten to a part in Mahoyo where she actually shows up, but reading about Kojika Kumari makes me pair her with Richard because of "responsibility" and I think their personalities have more in common in not, even though she might dislike him at first for being eccentric.
Vlov and Anastasia is the only pairing that I look at from any sort of a "shipping" perspective cuz the image of the ice-themed knight and princess is very cute, although the tragedy in their backstories still plays into it.
For Tiné and Okita, it’s about putting aside your feelings for the sake of your duty. There’s more obvious or straightforward choices for her, like Lakshmibai, Vlad III and Geronimo.
For Tobimaru, I cursed him with Tamamo based off his snarky interactions with the assertive Aoko. I haven't played Samurai Remnant beyond the demo, but Lancer Jeanne's relationship with her Master, who is a revenge-fueled survivor of the Shimabara Rebellion, is described as "to remain with Chiemon and attempt to guide him away from his destructive path, or failing that, would choose to accompany him even into hell so that he would not face it alone." Harli Vorzak's whole deal is wanting to bring down the world of Mages as revenge, but she doesn't have what it takes to actually harm people for it (at least based off so far in the FSF anime, idk beyond that). And so, Jeanne could take on that burden. Thinking about it, it could be interesting to put Angra with her too.
As for Sola-Ui and Bao, there's a lot to unpack there, but I'm not really sure how to describe it myself. The most I can say beyond them having a few similarities is that I think Sola-Ui would really get off on the feeling of exerting control over her, something that she hasn't really gotten to do in her own life (similar to how she develops an obsession with Diarmuid because that love is the first time she's really felt anything). Since I didn't play FGO long enough to ever reach Lostbelts and I can only read about Bao, her side of things isn't something I'm confident on.
There’s no real reason for the nun in Mahoyo and Medusa. It's just vibes.
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