Akeno Himejima
Rossweisse
Grayfia Lucifuge
Kuroka Toujou
Koneko Toujou
Rias Gremory
Ingvild Leviathan
Ravel Phenex
Irina Shidou
Xenovia Quarta
Asia Argento
Yasaka
Suzaku Himejima
Ophis
Serafall Leviathan
Gabriel
Sona Sitri
Tiamat
Nyx
Le Fay Pendragon
Roygun Belphegor
Kunou (older)
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Thanks again to everyone who voted, I hope you are all happy with the final choices.
I know that this is quite a large number of characters, and honestly, a bit overwhelming to build a relationship that doesn't seem like the mc going around throwing Pokeballs at them, BUT, I will try my best!