Jack insists upon seeing to Ruggie’s every need, but Ruggie refuses to believe that a “proud wolf” like Jack would willingly obey a “lowly hyaena” like himself, to which Jack responds “If you don’t believe me, then that means I haven’t been working hard enough. I will do everything in my power to earn your trust, sir!”
When Grim expresses surprise that Ruggie is so reluctant to accept Jack’s help, Jack explains that he is “just trying to stay by his side at all times so that I can back him up if another student picks a fight with him. And every time he goes somewhere, I check to make sure it’s safe first. Plus, when a ball came flying at him today, I shielded him with my body. Is there something else that I should be doing?”
Jack says that he just wants to earn the respect of those he admires and he admires Ruggie, in particular, because Ruggie did not abandon Leona in his time of need and did everything he could to serve him.
Ruggie appears, panicking over a necklace of Leona’s that has been stolen by a crow, and Jack vows to finally be of use to him.
Despite being such a stickler for the rules Jack ditches an entire day of school in order to find the necklace, returning it and even lying to Leona.
Jack reveals that he used no magic to find the necklace and just climbed every tree in the school, checking crows’ nests throughout the night. Ruggie immediately suspects Jack of wanting to extort him for a finder’s fee, telling Jack outright, “I can’t trust you”.
Jack asks if they can enter into an older/younger brother relationship. (The localization here is perfectly accurate, but for the curious: Jack is literally asking permission to call Ruggie “aniki” for “older brother.” In a line that was embellished on EN, Ruggie turns down Jack’s request to establish a mentor/mentee relationship.)
Original Ruggie: I don’t need a big, burly younger brother.
EN Ruggie: Yeah, but I don’t need some protein-addled muscle freak nippin’ at my heels and beggin’ for advice.
Ruggie counteroffers with making Jack into his “underling” instead.
Jack says that he should’ve known that Ruggie wouldn’t make it easy for him, but, “Someday, I WILL earn your respect!”
Even so, Jack has a voice Iine of “Ruggie has a way of gettin’ me to do stuff without me even realizin’ it. It’s irritating.”
Jack very much does not enjoy being told what to do—particularly by Azul—and Ruggie claims that there is no point in him trying to give Jack orders. Despite this, Ruggie often gives Jack instructions in other scenes that Jack obeys without complaint.
The catalyst of the Port Fest event is Jack wanting to take Ruggie out to lunch to at a special restaurant in order to thank Ruggie for looking out for his cacti while he was away at a track and field competition.
Jack only ever refers to Ruggie as Ruggie-senpai, but the English localization is somewhat inconsistent: in the vignette where Jack is desperately trying to prove himself useful to Ruggie he says “Ruggie, sir” the entire time, but in every single other Jack/Ruggie interaction on EN he refers to him just as “Ruggie”.
In his original dialogue, Jack is always using “-senpai”.
Twisted Wonderland Reference Note 