More a romantic fantasy than a romcom per se, Serendipity was one of the pinnacles of what might be described as the silver age of the 90s romcom, which started around the turn of the millennium and lasted until the mid-2000s. Films at this time opted for fragmented, sprawling or experimental narrative structures, in an attempt to come to terms with the way that romance was increasingly mediated through digital life. In fact, this possibility was always embedded in the 90s romcom, whose golden age might be bounded by Sleepless in Seattle, which imagined a hyperreal romantic ether, and You’ve Got Mail, which cemented the same impulse in email, but without losing that ethereal sense of a magical “out there” either. Once You’ve Got Mail had revealed that the answer was email all along, future romcoms had to preserve the mystery ushered in by Sleepless in Seattle, while staying digitally-savvy as well.

Serendipity was perhaps the most elaborate and flamboyant response to this situation. The film opens with a meet-cute between Jonathan Trager, played by John Cusack, and Sara Thomas, played by Kate Beckinsale, when they both reach for the same pair of black cashmere gloves at Bloomingdale’s, during the Christmas season. We don’t learn much about these characters apart from the sheer fact of their meeting, which Sara immediately attributes to serendipity. After a magical evening together, which includes a date to Serendipity 3, the cult restaurant in the East Village, Sara comes up with a proposal – they’ll leave it to fate to decide whether or not they meet again, since they haven’t even disclosed their surnames to each other. Serendipity thus starts with a meet-cute, and ends with a meet-cute, and so constitutes an experiment in whether a meet-cute is replaceable, both as a phenomenon and as a trope.

This places Serendipity within a broader swathe of romcoms that were fascinated by online dating as a new structure of feeling – a new sense of romance as driven by contingency and propinquity above all else. While online dating doesn’t make a direct appearance in the film, you feel it everywhere in the renewed sense of the sheer chance of two compatible people meeting. It vividly took me back to the peculiar agony and ecstasy of trying to connect with someone, whether regularly or romantically, in the days just before widespread social media – when the internet was there, the possibility for connection was there, but most social media platforms didn’t exist yet. Throughout the film, director Peter Chelsom often reverts to French lounge music, evoking a cosmopolitan cruisiness, but also the internet cafes where these early moments of proto-connection so often happened – nodes that plugged you into the ether.

As a result, Serendipity is driven by a magical sense of porosity, as Chelsom searches for spaces in New York City that anticipate the digital sphere to come. In one scene, Sara and Jonathan are in adjacent cars, separated by a bike rider who is himself immersed in a pair of headphones. This interstitial space feels, now, like a vision of the ways that people would soon be mediated by a new kind of portable music media. Chelsom also uses a golf driving range, positioned on the Hudson River, to connote this new network. He tends to shoot it front-on, at night, producing a grid-like cross-section that’s remarkably similar to the style of The Royal Tenenbaums, released the same year, which also looks like a networked film alongside Serendipity. Finally, Chelsom returns, time and again, to the skating rink in Central Park, as harbinger of a more digital future. This is where Sara and Jonathan go on their first date together, and where they meet up at the end of the film, for the concluding meet-cute.

Chelsom tends to shoot the rink from an abstracted distance, so that its brilliant white light – a combination of ice and floodlights – looks qualitatively different from the rest of New York. It looks like digital light, the combined light of future smart phones, especially in the closing scene, when Jonathan sits down on it with the cashmere glove from Bloomingdale’s. As Chelsom shifts to medium shots, the rink seems abstract and tactile at the same time, like Jonathan is sitting on an inchoate touchscreen. When he glimpses Sara through the snow, the flakes are like individual bytes of data, literally immersing the two of them in a new medium, as the light from the rink reflects up through everything and subsumed them in its brightness.

Along with these digital, or proto-digital spaces, Chelsom resorts to more manic camera work than we’d normally find in a romcom. Most of the film occupies an queasy, uneasy cusp between traditional and hand-held cinematography. While there are static and stately scenes, they’re always on the verge of collapsing into hyperactive movements that suggest that Jonathan and Sara are partly communing through hyperspace. Their first date may start with ice cream at Serendipity 3, but it ends with Sara taking them to the Waldorf-Astoria, instructing Jonathan to take a separate lift, and then telling him to push random buttons to see if they end up on the same floor, resulting in a manic game as they jump in and out of the elevators, often amidst crowds of people, at random moments. In these kinds of scenes, hyperspace seems to be bleeding into everyday space, until the film cuts feel like digital hyperlinks. This enables, in Sara, one of the earliest appearances of the manic pixie dream girl – a figure capable of harnessing this new hyperreality around their own hyperactive tweeness.

In other words, Serendipity is about the space between the characters more than the characters themselves – about a new mystical-digital texture percolating through the romcom. At times it reminded me of Nancy Meyers’ The Holiday, which also revolves around physically distant characters, and depends on a similar mystical texture, which she provides through English snowstorms and the Santa Ana Winds. Like The Holiday, Serendipity uses a soulful New Age soundtrack to capture that texture, which it places in counterpoint to the loungier French music, although in this case the New Age vocabulary is not quite sufficient either. Eve, Sara’s best friend in Los Angeles, played by Molly Shannon, works in a New Age bookstore, so you’d expect her to be a mouthpiece for New Age mysticism. Instead, she makes fun of herself and her clients. Similarly, Lars, Eve’s fiancée in Los Angeles, played by John Corbett, is a New Age musician, but can’t compete with her mystical communion with Jonathan. The very fact that Eve returns from a life in Los Angeles to New York, on the cusp of her marriage, to seek out Jonathan, is itself a rebuke to this Californian New Age texturality.

Serendipity adds two main ingredients to this New Age atmosphere to fit it better to the feel of online dating, both of which are embodied in Sara and Jonathan’s experiment. After they part in New York, Sara writes her name on a second-hand copy of Gabriel Garcia Marquez’s Love in the Time of Cholera, in the hope that it will make its way back to Jonathan through one of New York’s many secondhand bookstores. Meanwhile, Jonathan writes his name on a dollar bill, in the hope that it will return to Sara in the same way. In order to understand the online dating marking, then, the film has to compound New Age philosophy with a mystical understanding of the financial market, and the circulation of cash, but also with a new mystical understanding of language, which would prove so critical in early online dating and social media, which was largely text-centric. You could see this as the logical conclusion of all the small or second-hand bookstores that dot 90s romcoms, as well as the next step beyond You’ve Got Mail, which turns on the amalgamation of a bookstore with an internet-bookstore.

Once this system is in place, Jonathan and Sara go in completely opposite directions to hunt down the novel and dollar bill. Whereas Jonathan tries to track Sara down using normal, analog sleuthing, Sarah goes the other way, relying on pure intuition to bring them together. As the film tries to chart a middle ground between these approaches, it grows increasingly haunted and fascinated, in equal measure, by the near-miss as the flipside of the meet-cute – by all the near-misses that must occur for a meet-cute to happen. As the connections keep intensifying and interlooping, Chelsom glimpses something akin to a quantum romance – a romance driven by the connections that might have happened, and those that didn’t happen.

Even when Sara and Jonathan do get together, then, the film is still driven by this acute yearning to connect that cannot be satisfied by any single connection. Their final reunion is beautiful, but also cursory, not unlike the final scene of You’ve Got Mail, which also takes place in a New York park (in that case, Riverside Park) and hovers for the most tremulous instant between real and virtual worlds before the credits roll. The result is a new kind of magical realism, or an extension of the 90s romcom into a late magical realism, as the pivotal role of Marquez’s novel, and its focus on romantic solitude, would suggest. If Meg Ryan and Tom Hanks had made a third romcom together, it would probably look a look like Serendipity, which tries to imagine the project of Sleepless in Seattle and You’ve Got Mail in the early 00s.