* {{Anvilicious}}: A fight breaking out in a hockey game at the exact second Alyssa confirms that she's had a very promiscuous straight past. This is why Kevin Smith says he's best with dialogue.
* 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!!!!
* FairForItsDay: The film was an honest attempt by Smith at depicting and exploring the complex feelings that can arise from the intersection of heterosexual and homosexual relationships. [[spoiler:And it ain't ''just'' about Holden/Alyssa, either, and moreover one of his "big points" seems intended to be that it's more complex than a clear dividing line between "straight" and "gay".]] And Lord knows that even in 1997, a movie that treated lesbians [[spoiler:and gay men]] like regular human beings with regular human feelings was a rare enough unicorn. These days, though, the film often gets more than a little criticism for the lesbian characters having a lot of "sterotypical" lesbian traits and characterization, and for the concept of "convert a lesbian to straight by being man enough!" even coming up as a concept, despite the film being unequivocal about the character saying it being an idiot. [[spoiler:The ending making things ambiguous on that front doesn't help matters, either, even if what Smith ''wanted'' to do was point out that it's always more complicated than a binary divide.]]
** Given much of the criticism over the handling of Alyssa's character has echoed a long-enduring complaint of Queer female sexuality being viewed solely through a Straight Male point-of-view- and it also doesn't help that the main story is rumored to actually be based off a male producer's crush for a lesbian colleague, which would seem to confirm a slightly uncomfortable and unintentionally homophobic wish-fulfillment fantasy.
* FridgeHorror: While Banky's statement about lesbians "needing a good dicking" most likely wasn't ''intended'' to imply [[https://en.wikipedia.org/wiki/Corrective_rape corrective rape]], the fact that that's exactly what he's describing when he says that is unnerving to say the least.
* FridgeLogic: Didn't Holden, before he found out Alyssa was gay, wonder what she'd been doing on a panel for minority comic creators?
** Perhaps he thought it was because she was a woman -- even today, though by a smaller margin than when ''Chasing Amy'' was made, female comic book creators are still greatly outnumbered.
* 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.
*** Even moreso in 2015 when it was revealed that Jughead was canonically [[{{Asexuality}} asexual]]
** 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 ''ComicBook/{{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.
* 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.
** 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 know's won't love him back, but it doesn't excuse how selfish he becomes when he starts insisting that the other person love him on his terms.
* MisaimedFandom: The character who believed that a lesbian could be "converted" by the right man. Said character is also shown to be an idiot.
* 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."
* 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.
** It's hard to get too worked up about the BigDamnKiss when one of the Big Damn Kissers ''just'' got done delivering an epic TheReasonYouSuckSpeech berating the other for daring to attempt to change her orientation, making her either a {{hypocrite}} or a liar.
* 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.
* SomeAnvilsNeedToBeDropped: Getting angry at your partner about their sexual past just because that past makes you feel sexually inadequate, and expecting them to love you on your terms, is petty, and can destroy an otherwise good relationship if you don't deal with it the right way.
* 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]].
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