Yes, an emerging comic book bro successfully courts a (supposedly gold-star) lipstick lesbian in Chasing Amy, Kevin Smith’s 1997 comeback following his ill-received sophomore feature Mallrats. Please try to refrain from audible scoffs and dramatic eye-rolling, it’s not nearly as ridiculous or cringey as it sounds. The film was a total success upon its release, garnering raves from high-profile critics and killing at the box office—a surprising feat for a relatively small-budget flick that focuses on a hyper-specific brand of Gen-X dirtbag narcissism. However, Chasing Amy also touched a cultural nerve, a necessary prodding that might now appear tasteless in its prickly engagement with ‘90s-era (namely queer) identity politics.
As opposed to causing major offense at the time, it was instead heralded as a freshly funny feat within a genre overrun by increasingly shallow and inconceivable premises. As a rom-com, Chasing Amy dares to delve into depressing desire and the self-sabotage inherent to insecurity—something all but unfathomable in then-recent hits like While You Were Sleeping and My Best Friend’s Wedding. This is what makes it Kevin Smith’s finest movie: It’s so, so real. In its messy, unresolved central relationship, in its engagement with subculture posturing, in its admittance of Smith’s real-life love losses. Poignantly, bitter reality often prevails over fanciful romance.
Holden (Ben Affleck) and his best friend Banky (Jason Lee) are promoting their small-press comic Bluntman and Chronic at a New York City convention when they meet the magnetic and beautiful Alyssa (Joey Lauren Adams) supporting her comic Idiosyncratic Routine. Intrigued by her gregarious nature and similar stake in the then-culturally maligned world of comics, Holden is immediately smitten—which is why he champs at the bit to meet her the next night, even if it means driving from Red Bank, NJ through the Holland Tunnel into Manhattan. As it turns out, he’s been invited to a lesbian bar as a platonic date, mere conversation fodder until Alyssa’s hookup Kim (Carmen Llywelyn, Lee’s then-wife) arrives. The two women spend the rest of the night eating each other’s faces—Banky has no problem voyeuristically gawking; Holden seethes with envy.
Lesbianism is a newfound form of rejection for a man whose love life has been, as it seems, terribly uneventful. While Alyssa and Banky momentarily bond over their literal oral sex scars (an overt Jaws reference), Holden scowls in the corner, totally unamused by the idea of chiming in. Citing 1:30 A.M. Tunnel traffic, Holden drags Banky out of the bar, heartbroken and dejected. Nevertheless, Alyssa shows up on his doorstep the next day, ready to address the awkwardness and make peace. After a brief confrontation over her sexuality and a reconciliation that involves Alyssa miming the act of fisting to answer Holden’s daft questions concerning lesbian sex, it would appear the two were now the closest of friends.
But it’s all a flimsy emotional ruse. As they spend more time together, Holden falls harder—hanging onto the delusional notion that Alyssa might be wooed by his mere presence. At first, this suggestion feels insulting, reducing the central love interest’s sexuality to a challenge for its protagonist to overcome. When Alyssa and Holden finally share a passionate, rain-drenched kiss after he professes his love to her (though she first renounces his affections), the viewer’s worst fears are confirmed: All this lesbian needed was “the right man,” and then she’d be returned to the clutches of heterosexual normalcy. However, this occurs roughly halfway through the film’s 112 minutes, making this moment far from a happy ending. It doesn’t take long for Holden to find something else about Alyssa’s sexual past to get hung up on. This is the entire point of Chasing Amy: Just because a relationship is able to thrive in the face of improbability doesn’t mean it’s necessarily sustainable. In all likelihood, even if Alyssa were straight, Holden would have self-sabotaged—it’s his sense of identity that needs a major overhaul, not the “converted” lesbian.
Actually, the leap to dating Holden proves somewhat less dramatic to Alyssa than she previously made it seem. Though she identified as a lesbian during this period of her life, her sexual history is much more fluid. She’s engaged in and enjoyed sex with men and women alike since high school, whether it be group sex with two male classmates (earning her the crude senior year moniker of “finger trap”) or eating a girl out in the backseat of her car. In fact, it appears her attraction to women is predicated on emotional connection. “I haven’t liked a man in a long time,” she says to Holden while swinging on a typical New Jersey suburban playground. “And I’m not a man-hater or something. It’s just been some time since I’ve been exposed to a man that didn’t immediately live into a stereotype of some sort.”
Later during that conversation, when playfully challenging Holden’s own sexual proclivities, she takes a harder stance on her own lesbianism, going so far as to say she’s “never really been attracted to men.” This statement is proven to be historically false for Alyssa, whose sexual curiosity stemmed from a place of straight-forward pleasure-seeking. But this doesn’t discredit her previous label as a lesbian—it’s clear she’s simply experienced enough to know what she likes. “I’m more comfortable with the idea of girls,” she concludes.
The thing about secure, confident people is that their personal comfort is an ever-changing concept. Though Alyssa is initially upset by the prospect of disavowing her sexual identity to be with Holden, she quickly makes peace with the situation for the sake of her own happiness. She is ostracized by her largely lesbian friend group (“another one bites the dust,” a friend quips when Alyssa reveals she’s been seeing a man), loathed by Banky (who is so obsessed with destroying their relationship that he digs up the “finger trap” quote while doing his own hate-fueled research) and, on top of that, constantly commuting to Jersey. But she’s as happy as she’s ever been.
Holden, on the other hand, is absolutely miserable. When Banky tells him about Alyssa’s unkind superlative, Holden is eventually consumed by jealousy and spite, having believed that he was the first and only man Alyssa had ever slept with. Somehow, he wasn’t at all intimidated by all of the amazing, Earth-shattering sexual encounters his girlfriend shared with countless women—but the knowledge of pubescent sexual shenanigans (likely mediocre and clumsy) crosses a boundary. Alyssa is no longer the impossible prize—the lesbian who lapses into heterosexuality when “good dick” shows up—but a whore who’ll give it to anyone. Obviously, Holden never really loved Alyssa, he just loved the part of her she let him get to know. Similarly, he reveals his deep-seated insecurity, casting an immediate (and eternal) shadow over their relationship.
It’s been oft-noted that Chasing Amy is the creative byproduct of Smith and Adams’ own ephemeral yet torrid relationship. They began dating after filming Mallrats and their partnership dissolved due to (somewhat) similar circumstances. Smith found himself irked by Adams’ sexual resume. In comparison, he felt inexperienced and inadequate. Effectively ruining everything for himself, Smith seemed to see the error of his ways pretty quickly, and as such perhaps felt a duty to relay this personal fuck-up to a wider audience. In collaborating with Adams, he also gives her a voice in the process, eliminating an authoritative one-sidedness that often plagues these kinds of semi-autobiographical romance movies (think about how mean-spirited 500 Days of Summer feels after aging just over a decade).
Chasing Amy is both a love letter to Smith and Adams’ short-lived romance and an admittance of guilt on the filmmaker’s part in its one-sided dissipation. Perhaps they would have inevitably broken up due to other stressors, but Smith’s admitted closed-mindedness thwarted their coupling before it lasted long enough to get complicated. In the end, Holden and Alyssa realize they’re in completely different places in their lives, a fact made clear when his big plan to bridge their gap turns out to be proposing a threesome between himself, Alyssa and Banky (whose latent homosexuality supposedly manifests in grating homophobic comments). Whether this dynamic stems from a real-life situation is unclear (the film’s lesbian angle certainly didn’t), but the self-absorbed misunderstanding of the relationship’s core issue certainly feels believable.
So, yeah, Chasing Amy involves a self-identified lesbian falling for a straight man. However, this isn’t some gross male fantasy played (literally) straight. One year after their break-up, Holden sees Alyssa at a comic convention and slips her his latest project: Chasing Amy, named after the girl who Silent Bob uncharacteristically monologues about. While Alyssa is not the eponymous character in the comic, she is the principal one. Forgoing Chronic and Bluntman’s superheroism and drug references, this comic tells the story of their relationship—their introduction, friendship, romance and ultimate decoupling. Though she’s touched by the gesture, this reconnection doesn’t feel amorous. After all, Alyssa is attending the con with her new girlfriend and Holden doesn’t stick around long enough to intrude.
Only catching a glimpse of Holden, Alyssa’s girlfriend asks who she was speaking to. “Just some guy I knew,” she responds, followed by the film’s last line of dialogue: “So, what do you want to do tonight?”
Alyssa and Holden may have moved on, but that doesn’t mean the experiences they shared must be hidden away in shame. Their love felt special, and as such should be celebrated—while also making room for admitting where Holden’s useless societal hang-ups hindered what could have been a fantastic relationship. Particularly when it came to his distorted, ill-informed view of queerness and sexuality, he couldn’t find solace in dating the once-unattainable lesbian when she shifted her own sexual identity to welcome his love. Perhaps because Smith was so displeased with his girlfriend’s (presumably) heterosexual history, he wanted to broaden his insights in Chasing Amy to include a spectrum of sexuality he had largely been ignorant about beforehand (though let’s face it, his engagement with queerness isn’t flawlessly executed).
In having Alyssa’s character redefine her entire sexuality for Holden only for him to have a meltdown over her previous heterosexual experiences, Smith underlines just how insanely rigid the confines of traditional masculinity are. Alyssa having previously only had women as sexual partners feels less threatening to Holden because it is unknowable to him, but the idea of other men in the picture sends him in a testosterone-fueled frenzy. (Personally, I’d be more insecure about measuring up to lesbian sex as a cishet man.) There’s something about “planting a flag” that caters to the male desire for conquest—the same kind of senselessness that fetishizes virgins—and having that fantasy dashed is enraging for Holden. Much like his immature namesake, he must dispel this myth of masculine exceptionalism if he wishes to forge genuine human connection.
Truthfully, individual identity is totally and eternally malleable. Love is often not easily categorized and, as such, who we fall in love with can feel equal parts exciting and confusing. What remains true about queerness is that its definition can often be interpreted differently for individual people and their broader communities. That’s honestly what’s so appealing about embracing it: In a world of fixed gender roles and sexual expectations, it’s refreshing to exist on the periphery of the unknown. For most queer people, the notion of dating the milquetoast Affleck certainly doesn’t read as radical love free of societal mores. But if you’ve been engaging in menage-a-trois and moving vehicle cunnilingus since high school, a dorky comic book artist on the brink of an MTV series deal might just be the desirable unknown you’ve been craving…until he’s not. And that’s okay, because life goes on—and like-minded lesbians will still be around when you’ve gotten over him.
Natalia Keogan is a freelance film writer based in Queens, New York. Her work has been featured in Paste, Blood Knife and Filmmaker magazines, among others. Find her on Twitter.