History VisualNovel / MyTwoFirstLoves

** Principal Jim Jennings is an EvilPrincipal who forces his son Mason to follow in his footsteps and calling him a disappointment after he refused to, and later [[DisproportionateRetribution destroyed Mason's model airplanes and threatened to evict him for sneaking out at dawn]] to help Emma with her photography project. By the end of Chapter 72, he has royally pissed off Emma, Noah, Ava, Emma's father, and even ''his own son'' to the point where it's hard to feel bad for him when [[spoiler: he has a heart attack]]. From around Chapter 80 or so to Chapter 91, he goes further and further into this territory with every chapter; he bribed the Air Force to get Mason in (not for Mason's benefit, but his own), as it's revealed that he's been accepting bribes from rich parents to get undeserving students into college for years. When Emma and her friends try to dig up dirt on him, he brutally and gleefully punishes them all, before planning to have Noah (and later, the rest of the gang, including ''his own son'') expelled to save his own skin.

** Principal Jim Jennings is an EvilPrincipal who forces his son Mason to follow in his footsteps and calling him a disappointment after he refused to, and later [[DisproportionateRetribution destroyed Mason's model airplanes and threatened to evict him for sneaking out at dawn]] to help Emma with her photography project. By the end of Chapter 72, he has royally pissed off Emma, Noah, Ava, Emma's father, and even ''his own son'' to the point where it's hard to feel bad for him when [[spoiler: he has a heart attack]]. From around Chapter 80 or so to Chapter 91, he goes further and further into this territory with every chapter; he bribed the Air Force to get Mason in (not for Mason's benefit, but his own), as it's revealed that he's been accepting bribes from rich parents to get undeserving students into college for years. When Emma and her friends try to dig up dirt on him, he brutally and gleefully punishes them all, before planning to have Noah (and later, the rest of the gang, including ''his own son'') expelled to save his own skin).
** Lauren Young is an AlphaBitch in spades, mocking Emma for being "in zombie mode" for most of her freshman year (during which time her mother had ''died from cancer''), acting rude and catty to pretty much everyone, being lazy while still bossing people about, and flirting with boys despite their noticeable uncomfortableness. Much like Principal Jennings, she gets worse as the story goes on, deliberately dropping Emma during the cheerleader routine and blaming her for it, treating Emma and her friends like slaves while in charge of Winter Wonderland, locking them in the gym overnight when they call her out on this, ''smashing Emma's camera'' after forcing her to beg for her not to, and gloating about how she will be getting into college despite her poor grades and laziness in her extracurriculars, due to [[spoiler: her parents' bribery of Principal Jennings]]. Even when struck with LaserGuidedKarma, she refuses to admit any wrongdoing, instead blaming Emma and her friends for "ruining her life".

* ParentalFashionVeto: On the first day of school, Emma plans to wear an off-the-shoulder [[BareYourMidriff crop top]] and a tight miniskirt. Her dad makes her change, but she can sneak it out as a diamond option.

* LaserGuidedKarma: [[spoiler: By the end of the story, Principal Jennings has been arrested for his crimes and Lauren has had her college acceptance revoked. Elijah may also be in prison if you chose to turn him in]].

* TotallyEighteen: After Pixelberry received backlash for possibly portraying minors in a 30-diamond scene, they revised chapter 55 so Emma states that she, Mason, and Noah are all eighteen after Elijah claims they are minors.

-->'''Noah''': Because you realized that all the money in the world couldn’t save you from what happened to me if you got caught.

-->'''Noah''': You were right. We are exactly the same.