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SHIHOUIN YORUICHI. A talking cat isn't something you get to see everyday, so Ishida's first reaction when first meeting Yoruichi is rather... colourful XD However, they seem to have a really balanced relationship. They treat each other with the most respect and are very much equals intelectually and in terms of maturity.

SHIBA GANJUU. Is probably difficult to find two people with more different personalities that these two. However, since Ganjuu decides to go and help with the rescue mission, he and Ishida become comrades. Their interaction is very little and Ishida even gets to tell him not to call him by his first name, since they're not that close XD

KUROTSUCHI MAYURI. If there is someone whom you can say Ishida really truly hates, that is without any doubt, Kurotsuchi Mayuri - Captain of the 12th Division of the Gotei 13. Apart from looking like evil reincarnated, he's actually the one directly responsible of Ishida's sensei's death... and tons of other evil doings.