Zangetsu had to teach Hichigo a lot of things. And, since just-awakened zanpakuto spirit had some... Difficulties with concentration, the best course of action turned out to mix lectures and calm activities with sparrings.

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Zangetsu had to teach Hichigo a lot of things. And, since just-awakened zanpakuto spirit had some... Difficulties with concentration, the best course of action turned out to mix lectures and calm activities with sparrings.

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...But they always, always try to.
Looking at my old drabbles of Zaraki Kenpachi / Old Man Zangetsu (+ rusty_paths au) and. They are so much not like I am writing now. (For example, this is not my active OTP anymore, though I still like it.) They may be are not very good or plot-consistent (well, they are drabbles)... But they are so *alive*. Don't remember the year when I wrote those, but it was quite a long time ago, I think?
Kinda want to translate them to English to find new inspiration, but I am afraid the live and emotions will be lost...
You see, the problem is not that he does not know when to give up. The problem (from others) is that he just. Does not give up.
It is actually one of those things he and Ukitake have in common - stubbornness to the level of refusing to die.
Out of those two, who can possibly wreak more chaos over Seireitei?
From the one side, we have Getsu:
Less then hundred years short from being a thousand years old zanpakuto spirit with reading as one of his favorite hobbies.
Calm. Concentrated. Introverted. Can be seen meditating on the top of (former) Sokyoku hill.
Is concerned over all (yes, including Senbonsakura) zanpakuto spirits wellbeing. Can and will intervene when witnessing shinigami abusing their weapons.
Has lectured countless shinigami over concept of active consent and consent overall. (Usually when being in the form of shinigami himself, Ri Hanaro from the Thirteen Squad, but it is the story for another time).
Strongly disapproves of any alcohol consumption.
Is wary of scientists. Especially ones who engage with studying souls.
Has a long history with Kuchiki clan. Usually ignores it. Captain Kuchiki ignores him too.
Respects the concept of walls. Excluding the ones that belong to Kuchiki.
From the other side impatiently bounces on his feet Noba:
Not even full hundred years old mod soul who sometimes has difficulties with understanding of the concept of "personal items"
Can teleport, thus can infiltrate (almost) any part of Seireitei. Has no concept of "if the door is closed you are not supposed to be on the other side of it".
Likes to party with other mod souls, usually brings his own boose, since his metabolism makes it pretty hard to stay drunk and even tipsy. (No one asks where he gets so much alcohol. And why it looks so old.)
Hates the scientists. Won't go to Twelve's Squad territory unless there is no other choice.
I actually do not know the answer. Well, the easy answer will be "if you meet those two together on the war path - RUN." What were they up to separatedly:
Accompanying Yachiru in her quest of catching carps from Kuchiki's pond. Repeatedly. (Getsu. He also convinced her to relocate most of the fish to Ukitake's pond. Excluding the ones they ate.)
Fighting Kenpachi for fun. (Also Getsu.)
Being the reason the lower floors and labs of Twelve Squad were flooded. Repeatedly. With water, mice and semi-sentient slime. (Nova.)
Demonstratively breaking through Kuchiki's guards to visit a graveyard on an anniversary. The security gave up and started to turn the kudo spells off on this day, but the protection somehow activates back just to be loudly broken. (Getsu. He is making a point.)
Teaching Chad to smoke. Smoking weed with Chad. Facing the consequences. (Nova. Getsu was the consequences).
Making sure that Ichigo's gang will not be caught (too soon) when running through Seireitei. Wreaking more chaos. (Nova, with assistance of others. Getsu was busy teaching Hichigo to zanpakuto.)
Becoming a psychotherapist for Quincy Emperor. (Getsu. Yes, he also has no idea how and why.)

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Headcanons time!