[[caption-width-right:324: This [[BoardingSchoolOfHorrors old school]] has {{old school chivalry}} indeed, [[RecycledInSpace in the]] [[SnowMeansLove snow]]. ]]

* 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 - He's quite a {{Jerkass}} who often acts out for the sake of payment, though he has plenty of moments where he goes out of his way to help people, including:
** Helping Brandy destroy lawn gnomes that she feels are a mockery of her dwarfism.
** Helping Mandy cover up the embarrassing posters of her Earnest made.
** 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 has beaten, who weren't completely jerks.
** Helping Galloway cover up his alcoholism.
** Helping Edna get a date.