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1* DesignatedVillain: Caroline is viewed as a vapid, mean girl by Sam and her friend, when she never acts hostile towards either one of them throughout the film, and isn't even shallow as they believe she is. On top of that she is slut-shamed by both girls, is molested by a freshman- after her boyfriend hands her off to him, while she's completely inebriated, thus dumping her in a cruel manner, all because he found a new love interest in Sam.
2* EthnicScrappy: Long Duk Dong. He has an exaggerated Asian accent (which is played for comedy) and a gong sound effect whenever he shows up. He may be sympathetically portrayed and thrown a few bones, but he's still considered to be an offensively over-the-top racial caricature.
3* FairForItsDay: Long Duk Dong is a blatant stereotype and comes away from the story with more physical injuries than the other characters, but he's also had the night of his life and effortlessly found a really cool girlfriend.
4* FridgeHorror: If Caroline is already of legal age, her having sex with Ted could be viewed as statutory rape... even though it wasn't consensual for her.
5** Jake casually comments about how he could '[[DateRape violate Caroline six ways to Sunday]]' if he wanted to. Sam is alone with him at the end of the movie.
6* HilariousInHindsight: There's another character who is named [[Series/HannahMontana Jake Ryan in a sitcom]].
7** The Grandparents talking about how Rock n’ Roll is here to stay is quite funny since it’s all but dead by the 2010’s. Of course some may see this as HarsherInHindsight.
8* HollywoodHomely: A DiscussedTrope involving Samantha. It's even discussed between Jake and a friend of his (who is befuddled he'd consider leaving the sexy and built Caroline for the younger and less "mature" Samantha).
9-->'''Jake:''' Do you know Samantha Baker?\
10'''Friend:''' Sophomore, right?\
11'''Jake:''' Yeah, what do you think of her?\
12'''Friend:''' I don't.\
13'''Jake:''' Would you ever go out with her?\
14'''Friend:''' Depends on how much you pay me.\
15'''Jake:''' She's not ugly.\
16'''Friend:''' There's nothing there, man. It's not ugly, it's just void.
17* [[HoYay Les Yay]]: Even though Samantha and her friend are discussing Carolyn's relationship with Jake Ryan, Carolyn has no idea that the two are watching her showering, and the expression on Samantha's face just screams she wants Carolyn instead.
18** A more FanDisservice-y example; Samantha's grandmother wanting to feel her breasts. IncestSubtext?
19* OnceOriginalNowCommon: A landmark picture that had a major influence on the future of teen comedies, it's now regarded as a product of its time. The focus on teenage angst and sympathetic portrayal of losers and outcasts has been repeated many times over, and its use here has come under fire for stereotyping others ''and'' those it tries to present positively.
20* RetroactiveRecognition: [[Creator/JohnCusack John]] and Creator/JoanCusack make early appearances. He has a featured role as Bryce, while she's a wacky background extra with no lines—just a neck brace.
21* StrangledByTheRedString:
22** Their interest in each other is established early on, but Sam and Jake only ever talk to each other near the very end of the film before they have a romantic night almost entirely offscreen except for a brief moment coinciding with a kiss.
23** Ted and Caroline wake up together too drunk to remember what happened the previous night, but quickly are all over each other.
24* TheyWastedAPerfectlyGoodCharacter: Given the positively portrayed loser characters, you might think that Joan Cusack's neck-braced character might wind up having a good night like them, but instead we just see her in few short moments where we're supposed to laugh at her.
25* UnintentionallyUnsympathetic:
26** Ted is played as a ChivalrousPervert, but he can easily be written off as just a creep given he made money showing off a girl's underwear and took advantage of another girl while she was drunk. The latter act is more ambiguous, as he apparently got as drunk as Caroline offscreen before anything sexual happened. However, even if he wasn't in control of his actions then, he was before (if admittedly out of his depth) when he didn't get her home as instructed but mishandled and showed her off and got drunk. The former act while less serious is possibly worse given he knew full well what he was doing and did so even after bonding with Sam, continuing to take advantage of her kindness despite already winning his bet.
27** Jake's treatment of Caroline is also quite poor. Though she doesn't come off as a good girlfriend, he comes off no better in their relationship. His frustration with her partying may be valid, but it can be hard to sympathize with him over it since he doesn't try to actually talk to her about this, blowing her off throughout the night as he fixates instead on a girl he hasn't even talked to yet. And then, after she's gotten blackout drunk, he pawns her off to Ted, entrusting someone who doesn't even have a license to get his girlfriend home for him, while making light of her vulnerable state.
28* ValuesDissonance: So much of this movie would definitely not fly with today's audiences:
29** The male leads' casual encouragement of date rape is pretty cringe-worthy nowadays. Whatever may have transpired between Ted and Caroline is kept ambiguous and softened by the former having apparently gotten just as drunk as her offscreen. But the fact that both he and Jake were both sober when initially dealing with her intoxicated state gives their attempted drive home a very creepy edge.
30*** On the topic of their relationship, the casting of the 15 year old Anthony Michael Hall and the nearly full decade older Haviland Morris in a sexually intimate pairing would be considered inappropriate on the part of the filmmakers today.
31** The character Long Duk Dong is a pretty awkward walking, talking Asian stereotype complete with an exaggerated accent PlayedForLaughs and a gong sound effect whenever he shows up. In her 2011 analysis of the Creator/JohnHughes filmography, writer Susannah Gora outright called the character representative of how the 80's were the last decade in western history when such overtly racist jokes and caricatures were considered acceptable by the mainstream public.
32** The casual use of the word "fag" and "faggot" would be considered very un-PC. So is the word "retarded."
33*** For those aware of its meaning, "bohunk" (in reference to Sam's future brother-in-law) isn't much better. Made all the more noticeable by Sam's father using it in a scene where he otherwise comes off as a super nice guy and good father.
34** Nudity and dropping of the word "fuck" in a PG rated film would certainly catch many viewers off guard, especially the shower scene in the first quarter of the movie, which appears out of nowhere.[[note]]The PG-13 rating was only a few months away from being created.[[/note]] Though you can get away with a single use of the F word in PG-13 films nowadays, nudity, however brief, would land it an R rating without a doubt. Additionally, the nudity depicted being a high schooler (played by someone in their mid 20s) would not fly today even in an R rated film.
35** The treatment of geeks as weird and creepy social outcasts would be especially shocking today considering that geek culture is very trendy and mainstream. Ted and both of his friends being confined to tight spaces would also be considered unrealistically strong bullying.
36** The use of Creator/JoanCusack's neck-braced character (who can't seem to drink her fluids without difficulty and barely speaks) as a ButtMonkey reads as rather ableist now. As the student guide website [[http://www.shmoop.com/sixteen-candles/geek-girl.html Shmoop]] puts it:
37---> You know how mean everyone is, making fun of Creator/LisaKudrow for having scoliosis in ''Film/RomyAndMichelesHighSchoolReunion''? If you laugh at that, you are those people. That is all.
38** A very brief moment in the beginning, but Sam and her friend are having a discussion in the school hallway about what Sam wants for her birthday. Her friend suggests a pink Trans-Am and gorgeous guy, to which Sam replies that she would prefer a black one. Her friend looks HORRIFIED at the thought of her being with a black man and even asks, "A black guy???" But then Sam corrects her saying "Black Trans-Am. Pink guy." The relief on her friend's face after the correction is telling.
39** The film also stereotypes old people. Sam's grandparents are either so out of it that they can't see that a giant hunk of ash is about to drop off a cigarette, or (like her other grandparents) boorish and crude enough to not only actually discuss her breast size in her presence but actually ''touch them''.
40** Ted making martinis for him and Jake. The 80's was the last decade where kids would have been expected to mix their parents drinks for them, absolving the movie of needing to explain how he possessed such an age-inappropriate skill.
41* WhatDoYouMeanItsForKids: As mentioned above in Values Dissonance, despite being a PG rating, there's a lot of stuff in it that might be inappropriate for today's audience and the brief but clear nudity would absolutely get it an R rating today.
42* TheWoobie:
43** Sam. Her entire family forgets her 16th birthday because they're so focused on her older sister's wedding, and she's in love with Jake Ryan, who she thinks doesn't even know she exists.
44** The disabled girl with the neckbrace, who's merely used as comic relief, even though she clearly has a hard time being able to drink anything (from either a fountain or a can), and hardly seems to have any friends.

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