If you ask them, people will tell you with great confidence that there’s no way Lloyd Dobler and Diane Court actually make it after the credits roll in Say Anything… Their certainty is understandable — after all, they’ve had 25 years (the anniversary is today) to think about it. Even Diane herself seems uncertain, in that last scene; she asks Lloyd, “Nobody really thinks it will work, do they?” Lloyd confirms the fact, but then quickly adds, “You just described every great success story.” The question of their longevity usually boils down to a few basic ideas about compatibility — after all, she’s a genius and he’s (in her words) “basic,” a fast-talking, goofy Army brat who has hung his career prospects on the hybrid sport of kickboxing. “What’re you gonna talk about?” her father asks. “What do you have in common?” He asks these questions to break them up, unaware that his own dishonesty will not only bring them back together, but ensure that they do, in fact, last.

That people will still argue, two and a half decades later, about Lloyd and Diane’s ultimate fate says a great deal about how much we value these characters — and how real they are to us, because of the remarkably natural way that John Cusack and Ione Skye play them, and the enchanting dialogue writer/director Cameron Crowe put in their mouths. This was Crowe’s feature directorial debut, the next step in a career that went from teenage rock-writer prodigy (which he would later dramatize in Almost Famous) to undercover high-school exposé writer (with his 1981 book Fast Times at Ridgemont High) to screenwriter (with the 1982 Fast Times film adaptation). After his second script, 1984’s The Wild Life, failed to replicate Fast Times’ monster success, Crowe decided to take matters into his own hands and direct his next picture himself.

A key player in that transition was executive producer James L. Brooks, whose stock was still high after the Oscars of Terms of Endearment and acclaim of Broadcast News, and if Brooks’ recent films have been nothing to write home about, he still gets a lifetime pass — not only for the early work, but for helping make Crowe, Wes Anderson (Brooks was also executive producer for Bottle Rocket), and The Simpsons happen. Brooks’ Gracie Films partner, the late, great Polly Platt, was producer (and bit player — she appears as Corey’s mom, congratulating her at the graduation and warning her not to talk to Joe), and she brought in legendary cinematographer László Kovács, a collaborator from her New Hollywood days, to lens the film.

Crowe was 31 when Say Anything… was released, but — as he had throughout the ‘80s — he showed an uncommon faculty with the inner lives and speech patterns of characters much younger than himself. His script is remarkably evocative, indelibly capturing the anything-is-possible-but-I’m-totally-terrified feeling of the summer after high school graduation, when the future seems limitless, yet everyone is utterly uncertain. “How many of them really know?” Lloyd asks his guidance counselor (Bebe Neuwirth), of his classmates and their career plans, and it’s a good question. He’s not sure yet where he’s going. “I’m looking for a dare-to-be-great situation.”

Crowe’s characters stood in stark contrast to the teen films of the era; they were nervous and complicated and idiosyncratic, and that went for the grown-ups too. Just a couple of weeks before Say Anything’s release, Heathers hit theaters (its Queen Bee, Kim Walker, also pops up here as Diane’s air-quoting valedictory rival Sheila), and if that film was a rebuke to the world of John Hughes and an indication of the darker, more cynical tone teen films would take in the coming decade, Say Anything… plays now like the last gasp from that era, a warm and sympathetic portrait of the teen years where everyone, even the grown-ups, transcends their stock type. But it also points the way towards more sophisticated ideas about the relationships between men and women, specifically by creating a proto-feminist male hero whose best friends are girls, and who sees his male contemporaries as laughable stooges.

Though he’d done a handful of films before it (including Hughes’ Sixteen Candles), Say Anything… feels like the movie where the John Cusack persona really took hold — it was the role that would continue to define him for decades, with its offbeat intelligence and corkscrew line readings and the way his words tumble out of his mouth in nervous bursts (like his first face-to-face with Mr. Court, or the first phone call with Diane, where he keeps talking until he talks her into going out with him). “Look at those eyes!” he says of Diane at graduation, twice, beautifully encapsulating the way that everything about someone can seem perfect when you’re this kind of a smitten teenager. The object of your love and desire becomes all-consuming, and so do the feelings of despair when they break your heart. “I wanna get hurt!” Lloyd says at the end of the pre-title sequence, and it’s the kind of thing that only someone who’s never been hurt can say; later, when he demands that his sister “get in a good mood,” the scene is mostly about his naïveté. He doesn’t know what real pain is. But he will. And that pain is what makes his iconic boombox scene so special; the camera pushes in past the image to the actor’s face, a mask of both hurt and determination.

Ione Skye didn’t quite manage to turn this film into a career the way Cusack did — Hollywood didn’t quite seem to know what to do with her, or maybe she just played Diane Court so well that they couldn’t see her any other way (in spite of excellent, type-busting work in film like Gas Food Lodging). This was one of her first films, and the performance is remarkably unaffected; there are scenes, like when she confesses losing her virginity (“I’m scared to death of what you must think of me right now”) that feel so personal, it’s less like watching than eavesdropping.

That said, much of the power of that scene is in the quiet reactions of John Mahoney as her father, and it’s a tremendous performance — one even more absorbing on repeat viewings, when you know exactly who he is and what he’s done. Theirs seems like the kind of relationship parents and children should aspire to, of openness and honesty and lack of judgment (“You can say anything to me, I hope you still know that”), and he seems like such a good man, we keep waiting for the turn, for the reveal that all this IRS stuff was just a big misunderstanding. But we don’t get it, he seems to still be waiting for it when Lloyd shows up at the prison (“She can’t still be angry about this.”)

What Mr. Court doesn’t realize is that by betraying that trust, he has made Diane and Lloyd even closer. She loses the one person she can count on — but, in the process, she gains one, and if the two of them don’t seem to have anything in common, they have one deeply shared experience: the feeling of being abandoned by your parents. Lloyd may not be able to talk Nietzsche with her, but he knows what it is to be alone, and he’s not going to let her feel that way. He is, as he tells Mr. Court, good at being with her, and if the father tries to stand in for a boyfriend by giving his daughter a ring at the beginning at the movie, she closes that circle by handing him the breakup pen at the picture’s end.

When I first saw Say Anything…, at a junior high lock-in during the fall of 1989, I didn’t get the closing scene at all — it seemed to just end, out of nowhere, on an incomplete note. Now, of course, I’ve lived some, and I know that the scene is perfect. Their hands are gripped tightly; they’re everything they’ve got. Lloyd calmly assures her that everything is normal during their takeoff (“Very standard for a 747”), and provides an immediately attainable goal: the little ding, which means they’re comfortably in flight, and everything is going to be OK. They look up at it, expectantly. Their time together has been dramatic, intense, tear-soaked, uncertain. But they have each other. They’re looking out for each other. Their whole lives are ahead of them. And when they hear the ding, everything is going to be OK.