* It's pretty clear that [[EvenbadMenLoveTheirMamas Jimmy loves his mom]], despite the tense interaction they have in the opening cinematic. When Gary [[YourMom insults her]] by saying she made her "living on her back", Jimmy goes [[BerserkButton berserk]].
* Despite treating [[TheWoobie Petey]] like crap for pretty much the entire game, Jimmy proves at the end that he truly does care for him: [[spoiler: Upon defeating Gary and untying Dr. Crabblesnitch, the latter tells the former that Petey should be the school's Head Boy (previously held by the now-expelled Gary), to which Jimmy agrees.]] Aww.
*** Add to that their final words to each other:
-->'''Jimmy:''' [[spoiler:Now, about that letter to my mother...]]
-->'''Crabblesnitch:''' [[spoiler:What letter?]]
* Jimmy in general is this though a major jerkass noteable instances include
** helping a severely depressed little person destroy lawn gnomes she feels are a mockery of her condition.
** helping Mandy cover up embarrassing posters Earnest made which Jimmy took photos of.
** helping Beatrice get her papers back from Mandy
** helping Zoe get revenge on Burton for [[spoiler: getting her expelled for reporting him for sexual harassment. Then getting her expulsion lifted. ]]
** trying to extend an olive branch to clique leaders he's beaten who weren't complete jerks.
** helping Galloway cover up his alcoholism
** helping Edna get a date

*** though often motivated by money he's shown he actually cares about people.