* 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 is bi/pansexual but identified as a lesbian before she met Holden or if she had only come to realize that she was after Holden [[IfItsYouItsOkay "converted her."]] Which interpretation you go for usually determines how much you enjoy this movie.
* {{Anvilicious}}: Between the DramaticThunder when Holden tells Alyssa that he loves her and the fight breaking out during a hockey game at the exact second Alyssa confirms that she's had a very promiscuous straight pass, you can see why Kevin Smith says he's best with dialogue.
* AwardSnub: The film was apparently a nose away from an Oscar nomination for Best Original Screenplay.
* BrokenBase: Considered to be Kevin Smith's best film by some of his fans, but considered a disappointment by those who were expecting a more straight-up comedy like ''Clerks'' and ''Mallrats''.
* CrossesTheLineTwice
** Hooper's deconstruction of the Franchise/StarWars saga as being covertly racist, countered by Banky, culminates with:
--> '''Hooper''': And ''[[Film/ReturnOfTheJedi Jedi]]''ís 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?\\
''[an enraged Hooper pulls out a gun, and shoots Banky repeatedly in a crowded auditorium]''\\
'''Hooper''': Black rage! BLACK RAGE!!!!
** Banky's "four way road" bit. It's only funny ''because'' it's wrong.
** Banky, at first, seems to only agree to Holden's proposal for [[spoiler:a three-way with his [[HeterosexualLifePartners best male friend]]]] in an innocuous "Why not?" sort of way. His response when Alyssa tearfully declines? "Thank god!"[[note]]The implication being that he knows he has feelings for Holden and wants him all to himself.[[/note]]
* 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.]]
* HarsherInHindsight: Alyssa's joke about losing her virginity in a town with the same name as the infamous Sandy Hook School Shooting.
* HilariousInHindsight:
** 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.
** 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.
** Creator/BenAffleck seducing a lesbian is a huge part of the plot of ''Film/{{Gigli}}'', too.
** Ben Affleck's character writing a comic about a stoner {{Expy}} of ''Franchise/{{Batman}}'' became this when he got cast as the [[Film/BatmanVSupermanDawnOfJustice Caped Crusader]].
** Speaking of [[RuleOfThree Ben Affleck]], the title of the movie itself becomes funny when the premise of ''Literature/GoneGirl'' -- which he starred in -- involves his character effectively chasing after the titular missing girl, who is '''also''' named Amy.
** 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.
* HoYay:
** 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.]]
** The [[HeroOfAnotherStory heroes of another story]], Alyssa's ex-boyfriends who nicknamed her "finger cuffs", certainly apply.
* 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).
* 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.]]
* 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.
* 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}}: 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.
* OneSceneWonder: Jay and Silent Bob show up eighty minutes into the movie, say their piece and leave. Their scene not only features Silent Bob's TheOneThatGotAway speech which kicks off the final act of the movie but also has some of the funniest dialogue in the movie.
* SocietyMarchesOn: While the depictions of queer sexuality are up for debate on their fairness, the scene of Alyssa playing the "pronoun game" by using gender-neutral pronouns rules out the possibility that she's referring to someone who's non-binary. That concept was unheard of in 1997, but it's acknowledgment is practically required, particularly among LGBTQ people, in TheNewTens
* 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.
* 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]].
* WinBackTheCrowd: After ''Film/{{Mallrats}}'' scared off all of the critics who loved ''Film/{{Clerks}}'', this film proved that Kevin Smith was not going to be a OneHitWonder.

----