History YMMV / ChasingAmy

* AuthorsSavingThrow: While praised for it's frank discussions on sexuality and relationships, the fact that its also a story written and directed from a cishetero man's perspective ''about'' a cishetero man's perspective of a lesbian/bisexual woman has not been without its critics. As such, Kevin Smith would later include a scene in ''Film/JayAndSilentBobReboot'' where Alyssa, who's adapting Holden's InUniverse comic book for Creator/{{Netflix}}, acknowledges that stories about female sexuality and sexual queerness are probably best left to the people who experience these things firsthand.

* HeartwarmingInHindsight: Holden eventually proves how much he learned from his profound mistake in ''Film/JayAndSilentBobReboot'', where it's revealed that, after giving each other some much-needed space, he and Alyssa eventually became best friends again, eventually fathering her and her wife's child.

* AuthorsSavingThrow: While praised for it's frank discussions on sexuality and relationships, the fact that it's also a story written and directed from a cishetero man's perspective ''about'' a cishetero man's perspective of a lesbian/bisexual woman has not been without it's critics. As such, Kevin Smith would later include a scene in ''Film/JayAndSilentBobReboot'' where Alyssa, who's adapting Holden's InUniverse comic book for Creator/{{Netflix}}, acknowledges that stories about female sexuality and sexual queerness are probably best left to the people who experience these things firsthand.

** The movie was produced and released in an era before concepts like toxic masculinity, male entitlement, and the hypocrisy of the DoggedNiceGuy mentality were as heavily politicized as they are in TheNewTens. As such, it has a lot more bite than most later works that ''do'' approach it from a socio-political standpoint.

* HeartwarmingInHindsight: Seeing Holden and Alyssa rekindle their friendship to be stronger than ever in ''Film/JayAndSilentBobReboot'' just proves how much Holden took his lessons learned from the events of this film to heart over the previous twenty years.

---> '''Hooper''': And ''[[Film/ReturnOfTheJedi Jedi]]'''s the most insulting installment. Because Vader's beautiful black visage is sullied when he pulls off his mask to reveal a feeble, crusty, old white man! They tryin' to tell us that deep inside we all wants to be white!\\
'''Banky''': Well, isn't that true?\\

'''Hooper''': Black rage! BLACK RAGE!!!!

--> '''Hooper''': And ''[[Film/ReturnOfTheJedi Jedi]]''’s the most insulting installment. Because Vader's beautiful black visage is sullied when he pulls off his mask to reveal a feeble, crusty, old white man! They tryin' to tell us that deep inside we all wants to be white!\\

** Hooper's "The Black Man Is God" button [[Creator/MorganFreeman became this]] in [[Film/BruceAlmighty 2003...]]
** Hooper accusing ''Star Wars'' of being racist. Take note that this was released two years '''before''' ''Star Wars Episode I: Film/ThePhantomMenace'', a movie faced a lot of accusations of racism with regards to [[TheScrappy Jar-Jar Binks]].
*** And in 2015, ''Film/TheForceAwakens'' has a black lead with John Boyega playing Finn.

** While discussing ''Series/DegrassiJuniorHigh'', Bankie says that he has a thing for girls who say "Aboot." The main characters in Kevin Smith's later film ''Film/YogaHosers'' are two Canadian girls who comically exaggerate their "aboot"s.

** Banky and Holden. SO MUCH. [[spoiler:It's [[WordOfGay text]], not subtext, that the reason Banky dislikes Alyssa so much is because he's in love with Holden and doesn't realize it]]. Not only that, but Holden points all this stuff out.
** Banky and Hooper keep antagonizing each other over the course of the movie, Banky trying to get Hooper to break character and Hooper trying to get Banky to recognize "obvious" homosexual references. [[spoiler: Also not subtext. Banky and Hooper end up a couple.]]

* IAmNotShazam: The female love interest is named Alyssa, not Amy.
** Though in Holden's comic (An InUniverse BasedOnATrueStory), the Amy character resembles Alyssa (a possible CompositeCharacter).

* MisaimedFandom: In-universe. The character who believed that a lesbian could be "converted" by the right man. Said character is also shown to be an idiot. [[spoiler: And a deeply closeted one, at that.]]
* MisaimedMarketing: Arguable. "Guy meets bisexual-identifying-as-lesbian girl, guy loses girl because of his hangups" doesn't sell as well as "Ben Affleck meets lesbian, Ben Affleck falls for lesbian, lesbian... falls for Ben Affleck." On the other hand, sexuality only plays a passive role in the story, which is more about how it's wrong to force someone to love you on your own terms, making the film's tagline "''It's not who you love, it's ''how''" a perfect summary.

* {{Narm}}
** The clap of thunder when Holden tells Alyssa that he's in love with her. [[SarcasmMode Subtle]].

* OlderThanTheyThink: Music/SoulAsylum's "We 3," which plays over the credits, was not written for the film. It actually came out seven years prior on their album, ''And The Horse They Rode In On.''

* SomeAnvilsNeedToBeDropped

* TearJerker: The entire last third, beginning with Holden verbally abusing Alyssa to the point of tears and ''continuing'' to do so after she apologizes for not being more honest with him, continuing on through Holden's intervention with her and Banky which ultimately ends up [[NiceJobBreakingItHero destroying his relationships with both of them]] to [[spoiler: their unspoken make-up in the epilogue]].
* ValuesResonance
** The movie was produced and released in an era before concepts like toxic masculinity, male entitlement and the hypocrisy for the DoggedNiceGuy mentality were as heavily politicized as they are in TheNewTens. As such, it has a lot more bite than most later works that ''do'' approach it from a socio-political standpoint.

* TheWoobie: Poor Alyssa really gets put through the wringer once Holden comes into her life. She's [[ForcedOutOfTheCloset guilt-tripped into coming out as bi]] when he won't accept that she doesn't reciprocate his feelings for her. Doing so costs her several lesbian friends, who consider her a CategoryTraitor, and to repay her for this selfless act, Holden [[SlutShaming slut shames]] her. [[WhatTheHellHero In public]]. Despite putting everything she can into their relationship, repeatedly telling Holden that she just wants to be with him, it all ends up being for naught as he's too [[{{Pride}} proud]] to accept it. You just want to give the poor girl a hug (and possibly beat the shit out of Holden) by the end.

** While the film still gets flack for being vague about bisexuality, it does depict sexual and romantic attraction in general as being far more fluid than binary division (the tagline is "It's not who you love, it's how," after all). Alyssa's struggles with presenting as a lesbian but being a closeted bisexual, for example, is one of the few on-screen depictions of bi-erasure. Both of these topics have become much more germane as LGBTQ+ visibility becomes more commonplace.

* ValuesResonance: The movie was produced and released in an era before concepts like toxic masculinity, male entitlement and the hypocrisy for the DoggedNiceGuy mentality were as heavily politicized as they are in TheNewTens. As such, it has a lot more bite than most later works that ''do'' approach it from a socio-political standpoint.

** No matter how much of a DoggedNiceGuy you think you are, your significant other is never, ever responsible for living up to your expectations in a relationship, especially if it concerns your own feelings of inadequacy. Getting angry at them for this is petty, and can destroy an otherwise good relationship if you don't deal with it correctly.

* MoralEventHorizon: For most of the movie, Holden is a fairly likable, if thoughtless, person who succeeds in making himself look like an idiot when he confesses his love to his lesbian friend and insists that she "give it a try." We'll call him lucky on that one. However, when he outs her about her devious sexual past ''in public'' and proceeds to follow and continue to verbally abuse her, you will stop feeling sorry for him.
* {{Narm}}

** The similarly on-the-nose symbolism when the film cuts between a hockey fight and Holden grilling Alyssa about her promiscuous past.
* OlderThanTheyThink: One might assume Music/SoulAsylum's "We 3," which plays over the credits, was written for the film, but it actually came out seven years prior.

* AccidentalAesop: The movie is about relationships in general, but it's largely been praised as a deconstruction of [[DoggedNiceGuy male entitlement]].

* AccidentalAesop: The movie is about relationships in general, but it can also be seen as a perfect example of just how toxic and selfish the DoggedNiceGuy mentality is.

* SomeAnvilsNeedToBeDropped: No matter how much of a DoggedNiceGuy you think you are, your significant other is never, ever responsible for living up to your expectations in a relationship, especially if it concerns your own feelings of inadequacy. Getting angry at them for this is petty, and can destroy an otherwise good relationship if you don't deal with it correctly.

** In a notable discussion of the film, Hooper theorizes that Archie and Jughead are gay lovers. This argument was finally put to rest in 2015 when Jughead was revealed to be canonically [[{{Asexuality}} asexual]].

* JerkassWoobie: Holden. Nobody can fault him for falling in love with someone he knows won't love him back, but they can and do for treating that person as if they owe him something when he demands that he love her on his terms.* MisaimedFandom: In-universe. The character who believed that a lesbian could be "converted" by the right man. Said character is also shown to be an idiot. [[spoiler: And a deeply closeted one, at that.]]

* JerkassWoobie: Holden. Nobody can fault him for falling in love with someone he knows won't love him back, but he deals with this by outright forcing that person to live him on their own terms.
* MisaimedFandom: In-universe. The character who believed that a lesbian could be "converted" by the right man. Said character is also shown to be an idiot. [[spoiler: And a deeply closeted one, at that.]]

* {{Earworm}}: The weird but cool opening theme [[https://www.youtube.com/watch?v=0HBPccYJuwE Tube of Wonderful]] by [[Music/SoulAsylum Dave Pirner]].

* JerkassWoobie: Holden. Nobody can fault him for falling in love with someone he knows won't love him back, but they can and do for treating that person as if they owe him something when he demands that he love her on his terms.

* AccidentalAesop: The movie is about relationships in general, but it can also be seen as a perfect example of just how unproductive the DoggedNiceGuy mentality is.

* AccidentalAesop: The movie is about relationships in general, but it can also be seen as a perfect example of just how toxic the DoggedNiceGuy mentality is and just how abusive it is to the person you claim to care about.

* AccidentalAesop: A DoggedNiceGuy is not an actual nice person.

* FairForItsDay: The film has seen much flack in TheNewTens for its "stereotypical" depiction of lesbian characters and narrow-minded view of homosexuality, especially since it's yet another depiction of the homosexual experience through the eyes of a storyteller who isn't homosexual. In 1997, this was fairly groundbreaking in its earnest depiction of homosexual characters, something that's sadly still rare enough to bear mentioning. It also sheds some much-needed light on the concept of bisexuality and general non-binary sexuality. [[spoiler:The fact that the ending is rather ambiguous has hurt its reputation a bit, and non-fans are quick to point out that Smith, despite his noble efforts, otherwise screwed up the film's ultimate message.]]

** In a notable discussion of the film, Hooper theorizes that Archie and Jughead are gay lovers. In 2011, Archie Comics depicted a same-sex wedding with Kevin Keller, the series' first (and, to date, only) major character who is openly gay.
*** The argument was officially put to rest in 2015 when it was revealed that Jughead was canonically [[{{Asexuality}} asexual]]
*** In the same scene, the argument [[NoodleIncident somehow escalated]] to Banky claiming that "Archie is not [[HotForTeacher fucking Mr. Weatherbee]]!" Then came ''Series/{{Riverdale}}'', which had a subplot of Archie getting into a sexual relationship with Ms. Grundy.

* SomeAnvilsNeedToBeDropped: Expecting your partner to love you on your terms and then getting angry at them because their sexual past doesn't live up to those terms (and makes you feel sexually inadequate) is petty, and can destroy an otherwise good relationship if you don't deal with it correctly.

* HarsherInHindsight: Alyssa's joke about losing her virginity in a town with the same name as the infamous Sandy Hook School Shooting.
** Holden's question "The Quick Stop girl died?" sadly became this with the passing of Lisa Spoonauer in 2017.

* {{Narm}}: A love confession shouldn't give one EndingFatigue.
* OlderThanTheyThink: One might assume SoulAsylum's "We 3," which plays over the credits, was written for the film, but it actually came out seven years prior.

* ValuesResonance: The fact that the movie was produced and released in an era before concepts like toxic masculinity, male entitlement and the hypocrisy for the DoggedNiceGuy mentality were as heavily politicized as they are in TheNewTens, it has significantly more bite now that such topics have become hot-button issues for the general public and not just the niche crowds of the late 90s.

* ValuesResonance: The fact that the movie was produced and released in an era before concepts like toxic masculinity, male entitlement and the hypocrisy for the DoggedNiceGuy mentality were as heavily politicized as they are in TheNewTens, it has significantly more bite in TheNewTens, when such topics have become hot-button issues.

* AccidentalAesop: Just because you're a nice guy doesn't mean you're entitled to your ideal girlfriend.
* AlternateCharacterInterpretation: A subject of contention among viewers is whether Alyssa knew she was attracted to men but identified as a lesbian before she met Holden or if she thought she was gay and [[IfItsYouItsOkay Holden managed to convince her otherwise]]. Which interpretation you go for usually determines how much you enjoy this movie.

** Unfortunately, this kind of situation is not all that uncommon in real life and often occurs in abusive relationships (see MyGirlIsNotASlut). Feeling jealous because of your partner's past is a symptom of retroactive jealousy - a condition related to OCD. It is manageable, but sometimes this may cause the end of a relationship. Some people never tell their partners about these feelings for fear of something bad happening, others obsessively ask questions.