[7.6/10] There are two settings in *When Harry Met Sally*. One is full of cutesy lines and the most stereotypical gender politics. The other is full of the sort of honesty and vulnerability about life and love that we still don’t get in any of the hundreds of romantic comedies that emerged from this movie’s wake. I roll my eyes at the former, revel in the latter, and find myself uncertain about how to reconcile the two disparate modes of this movie.

I’m reminded of the notion that every movie is a magic trick. Even the most naturalistic, cinema verite approach to a film is inherently bending details and stitching together contrivances to make a compelling story. There are parts of *When Harry Met Sally* that are not remotely realistic, with writerly monologues and overly-manufactured sequences that don’t begin to graze reality.

But when the movie is clicking, you don’t notice. The interactions are charming. The back and forth between the title characters is cute and the observational humor is funny. It isn’t real, but it’s hyperreal -- a heightened version of what interactions between men and women, and conversations about relationships are like. That can be another way to capture truth, to magnify and escalate, to pack in years of developments in epiphanies and rapport in a scant ninety minutes. At its best, *When Harry Met Sally* performs that trick so well that you wouldn’t even care to examine Rob Reiner’s (who directed the film) or Nora Ephron’s (who wrote it) sleeves.

And yet, there’s times when that funhouse mirror version of men and women toeing that line between disdain and affection feels cartoony and pat. A certain leeway must be given to a film made more than three decades ago. The movie possesses a certain *Men Are From Mars, Women Are From Venus* quality to it, awash in gender and relationship stereotypes that seem quaint and even backwards these days. There’s superficial notions of men as hound dogs and women as “practical” which flatten the diversity and multiplicity of people and their attitudes and sensibilities, which renders the intended universality of the movie’s observations oversimplified and, in places, worthy of offense.

But at the same time there is an openness to *When Harry Met Sally* that gives it a resonance despite the distance in time and the societal changes we’ve undergone since 1989. As caricatured as Harry and Sally seem at times, the movie gives them layers. As sexually mercenary as Harry seems, the film allows him to be wounded by his divorce, to apologize, to grovel, to be a pest but also earnest. As persnickety as Sally can be, the film allows her to be steely, to crumble in weaker moments, to give as good as she gets and stand up for himself.

It’s as though Reiner and Ephron can’t decide whether to make its main duo cardboard cutouts out of a stand-up comedy routine or fully-realize, three dimensional characters. That seems to change from scene-to-scene, but when the movie hews toward the latter, it’s a delight and even moving.

Much of that owes to the performances of the two leads. Meg Ryan overdoes it in places, but also brings a steadiness to Salliness, with a particular expressiveness in her facial expressions and body language. Sally’s easily the more likable of the two main characters, but Ryan imbues a humanity into the role that helps ground her character even in the film’s larger than life interludes. Billy Crystal’s take all but saves Harry, who verges on being unlikable for a good chunk of the film and never fully recovers. Crystal’s everyman qualities and funnyman deliveries create a sense of good will for the character that isn’t necessarily in the script. The combination of the two performers’ talents makes for a pairing that is more endearing than it has any right to be, which is a boon to a film built around it.

The same goes for the movie’s setting. The backdrop is more of a bonus than anything, but I’m not sure New York City has ever looked so cozy and inviting as it does here. Director of Photography Barry Sonnenfeld captures an almost impossible splendor in the city, from autumnal stretches of orange leaves in Central Park to snowy sidewalks and brownstones whose interiors are covered with books. A comedy doesn’t have to look this good to pass muster, but it adds to the beauty and character of the piece that subtly makes the major relationship on display more welcoming by the aesthetic company it keeps.

Likewise, there’s a creativity to the presentation that helps liven up the proceedings and make the romantic developments more unique. The simple choice to jump years down the timeline marks a certain distinctiveness here, imbuing some greater truth to the “We fell in love over a couple of months” trajectory that most romcoms adopt. It allows the film to find humor and insight in the changes that occur over the passage of time and give the rocky road along the way to Harry and Sally’s happiness greater scope.

It also allows the opportunity to break up the time jumps with little vignettes of old married couples describing how they met, a fun device that shows the multiplicity of how attachments can form. Clever cinematic touches like a split screen to show our title characters watching *Casablanca* together convey an intimacy across city blocks, and the script pairs worried post-hook up phone calls to close confidantes that the audience experiences in stereo. There’s tons of unconventional choices in how this story is told which, for as much as this movie has become the ur-romantic comedy, signify that this is not just another love story.

That’s what ultimately won me over here. I’ll admit, about ten minutes into *When Harry Met Sally*, I was cringing and regretting that I’d cued it up. The instigating post-college road trip between the future couple seemed to portend an obvious slap-slap-kiss trajectory, where both Harry and Sally learn to soften their hard edges and change their ways thanks to love and any number of silly contrivances. It’s a formula scores of movie’s in this film’s shadow have followed.

But this film doesn’t go down that path. It shows Sally and Harry still tweaking and resenting one another years down the line. It shows them only softening toward one another when both are in a vulnerable position after the end of a long term relationship and in need of someone who understands. It turns their romance into a slow burn rather than a series of ups and downs, spending more time on the two of them having become friends and confidantes before it makes them lovers. The hints are always there, but this isn’t a conventional romance, instead about two people coming to love one another before they even realize it, let alone become a couple.
That’s a powerful idea. Sometimes *When Harry Met Sally* buries it in romance clichés and backwards notions about men and women. Sometimes Ephron’s dialogue veers away from the enjoyably stylized to the conspicuously overwritten. Sometimes you wish somebody would just punch Harry right in the kisser.

Still, if you can move past those artifacts, the film hits on some real truths, wrapped in an exaggerated but endearing package, about how the road to love is not always a direct or easy one, but that it can still lead to someplace wonderful.