- Accidental Aesop: The movie is about relationships in general, but it's largely been praised as a deconstruction of male entitlement and toxic masculinity.
- Alternate Character Interpretation: A subject of debate 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 Holden managed to convince her otherwise. Which interpretation you go for usually determines how much you enjoy this movie.
- Author's Saving Throw: 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 Jay and Silent Bob Reboot where Alyssa, who's adapting Holden's In-Universe comic book for Netflix, playfully snarks that stories about female sexuality and sexual queerness are probably best left to the people who experience these things firsthand.
- Award Snub: The film was apparently two votes away from an Oscar nomination for Best Original Screenplay.
- Crosses the Line Twice
- Hooper's deconstruction of the Star Wars saga as being covertly racist, countered by Banky, culminates with:Hooper: And Jedi is 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 a three-way with his best male friend in an innocuous "Why not?" sort of way. His response when Alyssa tearfully declines? "Thank God!"note
- Hooper's deconstruction of the Star Wars saga as being covertly racist, countered by Banky, culminates with:
- Don't Shoot the Message: As mentioned above, the film has been dismissed by those who simply don't like the implication that Kevin Smith, a cishetero man, is speaking for a queer woman.
- Harsher in Hindsight
- Alyssa's joke about losing her virginity in a town with the same name as the infamous Sandy Hook School Shooting.
- Holden's line "The Quick Stop girl died?" Lisa Spoonauer, who played the character described, became the first actor from Clerks to die in 2017.
- Heartwarming in Hindsight: Holden eventually proves how much he learned from his profound mistake in Jay and Silent Bob Reboot, where it's revealed that, after giving each other some much-needed space, he and Alyssa eventually became best friends again.
- Hilarious in Hindsight:
- 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 asexual.
- In the same scene, the argument somehow escalated to Banky claiming that "Archie is not fucking Mr. Weatherbee!" Then came Riverdale, which had a subplot of Archie getting into a sexual relationship with Ms. Grundy.note
- Hooper's "The Black Man Is God" button became this in 2003...
- Hooper accusing Star Wars of being racist. Take note that this was released two years before Star Wars Episode I: The Phantom Menace, a movie faced a lot of accusations of racism with regards to Jar-Jar Binks. And in 2015, The Force Awakens has a black lead with John Boyega playing Finn.
- Ben Affleck seducing a lesbian is a huge part of the plot of Gigli, too.
- Ben Affleck's character writing a comic about a stoner Expy of Batman became this when he got cast as the Caped Crusader.
- Speaking of Ben Affleck, the title of the movie itself becomes funny when the premise of Gone Girl — which he starred in — involves his character effectively chasing after the titular missing girl, who is also named Amy.
- While discussing Degrassi Junior High, Bankie says that he has a thing for girls who say "aboot". The main characters in Kevin Smith's later film Yoga Hosers are two Canadian girls who comically exaggerate their "aboot"s.
- Ho Yay:
- Banky and Holden. SO MUCH. It's 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. Also not subtext. Banky and Hooper end up a couple.
- The heroes of another story, Alyssa's ex-boyfriends who nicknamed her "finger cuffs", certainly apply.
- I Am Not Shazam: The female love interest is named Alyssa, not Amy. Though in Holden's comic (An In-Universe Based on a True Story), the Amy character resembles Alyssa (a possible Composite Character).
- Jerkass Woobie: 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.
- Misaimed Fandom: 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. And a deeply closeted one, at that.
- Misaimed Marketing: 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.
- Moral Event Horizon: Holden only doesn't cross it when he confesses his love to his lesbian friend and insists that she "give it a try" because she turns out to be an even more deeply closeted bisexual, and only momentarily embarrasses both of them as a result. 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.
- The clap of thunder when Holden tells Alyssa that he's in love with her. Subtle.
- The similarly on-the-nose symbolism when the film cuts between a hockey fight and Holden grilling Alyssa about her promiscuous past. There's a reason Kevin Smith says he's better at dialogue.
- Older Than They Think: Soul Asylum'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.
- One-Scene Wonder: Jay and Silent Bob show up eighty minutes into the movie, say their piece and leave. Their scene not only features Silent Bob's The One That Got Away speech which kicks off the final act of the movie but also has some of the funniest dialogue in the movie.
- Some Anvils Need to Be Dropped:
- 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, no matter how much you think you've earned it. Getting angry at them for these sorts of things is petty, and can destroy an otherwise good relationship if you don't deal with it in a way that's best for both of you.
- All relationships, even platonic ones, are give and take. Neglecting the feelings of your friends is just as selfish as neglecting the feelings of your romantic partner and can similarly destroy the trust you have in one another.
- Tear Jerker: 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 destroying his relationships with both of them to their unspoken make-up in the epilogue.
- Values Resonance:
- The movie was produced and released in an era before concepts like toxic masculinity, male entitlement, and the "nice guy" stereotype were as heavily politicized as they are in The New '10s. As such, it has a lot more bite than most later works that do approach it from a socio-political standpoint.
- While the film still gets flack for being vague about bisexuality, it otherwise speaks positively to the fluidity of sexual and romantic attraction in general. 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 and both her promiscuity and the fact that she has to "come out" more than once would be considered less controversial and more in the field of "questioning" these days.
- Win Back the Crowd: After Mallrats scared off all of the critics who loved Clerks, this film proved that Kevin Smith was not going to be a One-Hit Wonder.
- The Woobie: Poor Alyssa really gets put through the wringer once Holden comes into her life. She's 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 Category Traitor, and to repay her for this selfless act, Holden slut shames her. 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 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.
YMMV / Chasing Amy