These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Darkness-Induced Audience Apathy: The movie can have this effect in comparison to John Hughes's other films, especially considering the cynical anti-establishment tone, the rampant Black and Gray Morality, and the ambiguous ending, all of which would be out of place in the more cheerful, carefree teen movies of the time.
Fan Fic Fuel: The rather open-ended ending on how it wasn't answered whether if the 5 actually stayed friends or not by Monday in which of course does rely on your stance in the Idealism vs. Cynicism debate. While there are viewers who went for the flat out Idealistic belief that all 5 of them stayed friends and the Official Couples (Bender X Claire and Andy X Allison) did truly last while others believed that they all went their seperate ways by Monday. However there are plenty who Took a Third Option and go with a bit of both. Either on how they all still stay to be friends but the Official Couples didn't last. Or some of them still stay friends while some of them don't (usually its either Claire and/or Andy that ditches them to stay with their cliques and its Bender, Allison and Brian that are still friends. However those who do this option are normally those who ship Bender with Allison). Or maybe those who had already admitted to or exhibited their own coldness drop most of the others (Bender and Claire), while those who said they wouldn't don't (Andy, Brian, and Allison).
Considering the rise of the Education Mama nowadays, watching Brian's subplot with his family may have this effect.
The story of Brian bringing a gun to school, regardless of the fact that it's a flare gun, wouldn't sound funny considering the recent school shootings and suicides, if the implication of him killing himself is true, that have been occurring.
Threatening someone with a knife, like Bender did, would be grounds of expulsion and even arrest charges in this day and age. Even if he didn't use it.
Ho Yay: One brief moment, when Bender tries to psyche out Andy.
Bender: You know, you're kinda sexy when you're angry.
Jerkass Woobie: Of all the five kids who have a troublesome background right behind their behavior, Bender in particular counts as such, big time. Andy to a lesser extent, as he's never portrayed as a jerk in the film, but rather hearkens back to something he did.
Moral Event Horizon: Threatening an abused kid in a closed room with a physical beating, really? Then going off to sneak peeks at confidential psychological files — and is caught by Carl, who promptly blackmails him.
Squick: Bender is offhandedly shown brushing his teeth with one of Claire's makeup brushes. Claire is later seen using the brush on Allison's face. Also, when Claire takes out her diamond earring and Bender puts it in his own ear without cleaning it. Anyone who's ever had infected piercings knows what happens next.
Strawman Has a Point: While sure it may come off that Claire was acting like a total bitch because of her response towards Brian's comment on if they're going to still be friends when the school week approaches she has made a good point that given each of the group's social classes the chances of them remaining friends Post Saturday Detention is pretty slim and pointed out the reasons why it wont be happening.
Values Dissonance: Both Bender and Andy use the word "fag/faggot" without being punished or reprimanded for it. Today, the word is seen as an insult almost on par with the N-word, but in The Eighties, the term would essentially be seen as just another swear, and doesn't imply that either of them were gay-bashers.
Brian's punishment of a Saturday detention for bringing a (flare) gun to school is shockingly laughable these days.
Conversely, for someone who went to a school which never had them, the idea of spending an entire Saturday - indeed, any length of time on a non-school day - can seem like cruel and unusual punishment! (Obviously not for bringing a gun to school, though).
There is a relatively minor case regarding the fact that Claire brought Sushi for lunch was a symbol of how wealthy her family is. Back in the 80's Sushi was a far more expensive dish that only the wealthy can get but over the years the prices have lowered and its more affordable. Granted Sushi is not perfectly cheap now but modern normal viewers are more likely to be able to get Sushi now than they were back then.