Flashback Film Friends is a series in which a Jezebel staffer watches a movie she or he has seen a million times, with a staffer who has never seen it once. Then they discuss—just like friends.

Kevin Smith’s romantic comedy Chasing Amy aimed to be equal parts charming and abrasive, sexual and political. At the time of its release, on April 4, 1997, the movie earned praise as a love story that tried to tackle honest conversations around sexual identity and fluidity, but what made it so risqué for its time is part of what makes us squirm two decades later. Ben Affleck stars as Holden McNeil, a comic book artist who falls for a fellow artist, Alyssa Jones (Joey Lauren Adams), despite discovering that she’s a lesbian. As the romance between Holden and Alyssa evolves from great to bad, he learns the truth about her sexual past—that she’s a woman who’s had sex with a lot of men! AHHH! By his side, Holden’s homophobic best friend Banky Edwards (Jason Lee) casually tosses around terms like “man-hating dyke” and feels no shame about his ignorance.

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Twenty years later, Chasing Amy feels at once dated and relevant to 2017. After all, this is an era in which our President manages to offend everyone and strives for regression on a daily basis, and where sad white men—the Bankys of today—long for the days when America wasn’t so politically correct. While I remember awkwardly watching Chasing Amy with a group of friends for the first time in my teens, Joanna Rothkopf had never seen it—“I literally just knew it was about lesbians,” she professed. On the occasion of the movie’s 20th anniversary, we both watched it recently. Here’s our delightful conversation.

CLOVER: I’ll preface this by saying I have a taste for bad romantic comedies—I will watch them all the time, any time—so take that into consideration. One of the reasons this movie happens to be relevant now is that it deals with the idea of political correctness and the politicization of sexual identity. The first time I watched it, I was around 13, hanging with a group of friends in one of their houses when their parents were away. I remember it being a bit scandalous at that age because of all the sex talk. I also remember cringing.

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The story is framed from the perspective of two white men (Jason Lee and a very young and badly-goateed Ben Affleck) who have their perspectives shattered by this woman both of them don’t really understand because her sexuality is fluid. Affleck’s character, Holden, “chases” her even though he knows (thinks) she’s not into men.

I expected for the movie to feel ancient when I rewatched it, but some of the issues around gender expectation and ignorance about sexuality still remain 20 years later. I thought it did well at setting up Point/Counter Points—some of it, again, very ignorant thinking—and I’m surprised that a Kevin Smith movie held up. But there is lots of mansplaining. What was your impression of how those themes were handled? And what, if anything, had you heard about the movie before?

JOANNA: I remember loving the Jay and Silent Bob movies when I was a teenager—specifically Jay and Silent Bob Strike Back and Dogma, the only two I’d ever seen. They were smart and cool and sexist but in like a smart, winky way, you know? I didn’t see Chasing Amy, not for any reason, I just missed it, and when you asked me to watch it I didn’t even realize it was in that Jay and Silent Bob universe to begin with. I literally just knew it was about lesbians.

Watching this for the first time, I would argue that it actually doesn’t hold up and is, in fact, a very bad movie that I hated! It felt like the pitch was, “A guy’s guy gets semi-woke while trying to date a lesbian.” And all the conversations between Jason Lee, playing the role of the Ignorant Misogynist whose every other word is “dyke” or “faggot,” and Ben Affleck (named Holden... HOLDEN!), the guy whose comebacks to Jason Lee, who he continues to be friends with, successfully gets a lesbian to fall in love with him and then dumps her because she was kind of slutty ten years ago. But also this was 20 years ago and I guess this was progressive back then?

C: I loved Dogma, too. This is a very hateable movie! I guess I mean it holds up as far as, people are having those same dumb conversations now and Lee’s character Banky reminds me of all the white dudes who want to be able to say offensive things without repercussion. That cycle of what’s acceptable on film is always interesting to me. I do wonder how much self-awareness there was in creating those characters. Like, how much were they making fun of the oblivious white dude versus playing into it? Banky literally asks, “How can a girl ‘fuck’ another girl?” And then there’s a whole debate about it.

And yeah, I was tight rewatching the romance part of it play out, which I didn’t really pay attention to when I was younger. The premise is that Holden is upset about Alyssa’s sexual past (she was nicknamed “Chinese finger cuffs”) enough to not want to be with her. It’s also sad that her character devolved from this confident fluid woman to kind of a romcom archetype. There’s that scene where she and Holden (Affleck) are laying in bed and she gives that speech about how “I got here on my own terms.” I guess that’s the end of this conversation, since you hated it.

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Just kidding. Was there anything you liked? Janeane Garofolo once described Joey Lauren Adams as a “baby voiced lesbian.” Her voice was always, like, a thing that I think guys loved.

J: I loved Joey Lauren Adams. I already loved her because of Dazed and Confused and, uh, Big Daddy. So her having a whole movie to herself, I was down with. The only part of her performance I didn’t love was when she and Ben Affleck are shrieking at each other outside the hockey match and it sounds like she’s really straining her throat and I wanted to yell, “Girl, please procure a lozenge and use your diaphragm!!” I liked when Matt Damon was in it for one second, being a douchey TV exec, and I liked Jay and Silent Bob’s brief appearance. I also liked Hooper even though the writing/direction realllly hammered home his black gay friend token role.

One thing that I also laughed at now, but wouldn’t have been able to laugh at if I had watched this when it came out, is how the movie talks about sex. Obviously, it’s super stylized, but the idea that main character Alyssa could be dirty because a guy whipped his dick out and ran around the house and then she decided to suck it and then another guy took out his dick and started having sex with her too is just too much. Do you think teenage boys are watching this and thinking that is how women like to be? Please god let me never encounter a man who was taught about sex from a Jay and Silent Bob movie!!!!

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C: The parking lot shrieking was a bit unbearable and the flashbacks from the dudes’ perspectives definitely reminded me of how teen boys, and I guess adult men, dramatize their sexual escapades. My favorite part is after that breakup scene where Alyssa is scream-crying and then the next scene is Ben Affleck shedding a single male tear. That’s all he’s allowed. My other favorite part is the Jay and Silent Bob conversation when Bob says the title of the movie: “You’re chasing Amy...”

There was some good commentary in the black gay militant character and how he felt like he had to hide behind masculine aggression. That’s part of why the movie was billed as kind of an anti-romcom, because there were these layers of social conversation happening beyond the love story. The Los Angeles Times review described it as “a little movie with big truths, a work of such fierce intelligence and emotional honesty that it blows away the competition when it comes to contemporary romantic comedy.”

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But I feel like the movie could be remade in a much smarter way today by a WOMAN. Then, there’s the ending where Holden proposes a threesome to work out their issues. The good ole threesome resolution that always fixes everything. Whether they get back together or not was sort of left open, going against romcom convention, but you still get the sense that they will. Realistic endings make for the best romcoms, though I would rather have seen Alyssa decisively not choose him.

J: I agree with the woman point!!! I kept thinking that this was trying to be a super smart movie about a woman’s sexuality, but it was written from the perspective of the ignorant dudes trying to understand her. And the Jason Lee character does keep saying things along the lines of, “Stop trying to fuck a lesbian, she’s never going to fuck you,” which, even though he says it obnoxiously, isn’t a bad point! Because eventually all Ben Affleck wants is to fuck her, and also date her. Which he does briefly, so congrats to him. Anyway, my point is—idea good, execution could’ve been less bro-ish. But also I am not a bro and who can say what they like? Not I.

I basically liked the ending, though I feel a little tepid about her being so cool with Ben Affleck after he was nothing but a jerk to her (first tries to woo her out of her lesbianism, then when he succeeds, gets mad she’s hooked up with other guys, then as an apology asks her to do the traditional deux ex threesome). I don’t know. When I was watching it I was very put off by how Social Justice for Bros I thought it was trying to be, but now that 24 hours have passed, I feel maybe like it is a pretty solid romcom for the less smart dude audiences of 1997. Sorry to be so mean to 1997!!!

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C: Haha. I totally see your point about the social justice bros. Holden is basically a Bernie bro and Banky would hate Hillary and spend like 20 minutes explaining why she’s the devil and then say, “Anyway it doesn’t matter, I didn’t vote.” I would love to know what Ben Affleck thinks of this movie now, in old age. Kevin Smith once explained why he made it—it’s well known that the story was based on his real-life relationship with Joey Lauren Adams and the way he unfairly projected his insecurities onto her.

He wrote in this 2000 piece: “The day I saw disbelief, outrage, and hurt reflected in the eyes of the woman I loved as she realized I was insisting that she apologize for her life up until the moment we met... well, that was the day it struck me that I wasn’t quite as liberal as I fancied myself and instead came to grips with the fact that I was rather conservative. And rather than enter therapy, I decided to exorcise my demons on screen. Chasing Amy was conceived as a sort of penance/valentine for the woman who made me grow up, more or less—a thank-you homage that marked a major milestone in my life, both personally and professionally.”

For a lot of people, knowing the story behind the movie might have added a certain sentimental layer. It’s a coming-of-age in that regard, self-reflection on the way people hurt people, especially when they’re at their most ignorant. I can tell that Kevin Smith wanted the Holden character to appear somewhat self-aware but still struggling to understand things, so I think that’s meaningful in its own little way. It’s a weird movie for sure.

J: I’m happy for Kevin Smith’s awakening. I really am!!