How ‘Serendipity’ Predicted The Demise Of The American Rom-Com
By: Kimberly Joyner
Tags: Film, Romance, Pop Culture, Dating, Internet

Credit: Tapestry Films

How ‘Serendipity’ Predicted The Demise Of The American Rom-Com

The early aughts classic rejects the romantic potential of internet technology that ‘You’ve Got Mail’ embraced.

If timelessness is a staple of the American romantic comedy, then 1998’s You’ve Got Mail broke all the rules of the genre. The film, about two people who fall in love over the internet despite being rival business owners in real life, is so wielded to the technology of the day (America Online, or AOL) that it would hardly muster romantic feelings in someone who did not experience the service firsthand. Even for those of us who are old enough to remember the anonymity and creative freedom of AOL’s chat rooms and instant messenger, the few years of their dominance aren’t really missed — AOL was soon replaced by much faster (and less deafening) broadband services. Today, having around-the-clock virtual connections to old love interests and potential new ones is the dating norm.

In the years since You’ve Got Mail premiered, seldom have romantic comedies attached themselves so overtly to the internet — technology just isn’t terribly romantic and rom-coms are in the business of being romantic. Serendipity, premiering just 3 years after You’ve Got Mail, echoed this sentiment by rejecting the internet entirely in deference to the tradition of the timeless rom-com.

Beyond the dreamy, snow-drenched New York City streets in Serendipity lies deep anxiety about love in the new millennium. Real love, the sort that people would pay money to experience vicariously through film, needs an element of long-suffering; and Serendipity predicted that the connections made possible by the internet were going to be love’s — and the rom-com genre’s —downfall.

The Demise of the Rom-Com

Film and pop culture critics have lamented the demise of the rom-com genre for years, but theories on why rom-coms in the 2010s have failed to capture the audiences of their heydays in the 90s vary substantially. For instance, Elena Sheppard writes for Nylon that the decline of rom-coms in recent years reflects the material anxieties of life after the Great Recession. Moviegoers simply aren’t in the mood to watch “lavish, comfortable upper middle-class lives projected from on high,” Sheppard says. In contrast, New York Magazine’s Jen Chaney argues that rom-coms haven’t died so much as they have shifted their focus to more authentic and inclusive portrayals of love. The rise of Barack Obama as the first black president in the 2010s ushered in a wave of cultural prominence for black Americans in media; and his administration’s leftward push on LGBT civil rights followed a decade of increasing representation of LGBT characters on TV and film. These just don’t happen to be the kinds of films that break box office records.

A third perspective on the demise of the rom-com is the one Serendipity intimated a decade earlier — the internet would disrupt the genre as we knew it by making long-suffering love a thing of the past. The film, with its silence and moments of hostility toward the internet, suggests that the speed and efficiency of online dating does not make up for the magic of the unexpected encounter — in our lives or in the ones we watch on film.

“A Fortunate Accident”

When Sara (Kate Beckinsale) and Jonathan (John Cusack) first meet, Sara is pretty straight-forward about letting fate determine the choices she makes, and she spends much of their first evening out together looking for signs to tell her if she should pursue a relationship with Jonathan.

The pair have their first fateful encounter at Bloomingdale’s during the Christmas season shopping rush, both going to grab the same pair of black gloves on a display. To thank Jonathan for allowing her to keep the gloves, Sara takes Jonathan out for coffee at a restaurant called Serendipity. Sara explains that she has always liked the name Serendipity and the idea of life being a series of fortunate accidents, although she prefers to think everything happens for a reason. Jonathan isn’t as convinced but he likes Sara too much to challenge her thinking. At first, Sara decides not to see Jonathan again and leaves Serendipity without ever giving him her name. But when they both return minutes later to retrieve items they left at the restaurant, Sara is convinced this is a sign that she should go out with Jonathan that evening.

Towards the end of their night out, Sara agrees to give Jonathan her number on a scrap piece of paper. But just as she does, a gust of wind blows the paper out of her hand, and she is close to certain this is a sign that she is about to make a mistake. Jonathan tries to convince her this is no big deal, but Sara is unmoved. Instead of exchanging phone numbers directly, she makes Jonathan write his phone number on a $5 bill she eventually uses to make a purchase and writes her number in a copy of the novel Love in the Time of Cholera that she plans to sell the next day.

Credit: Tapestry Films

In one final desperate search for a sign that they should be together, Sara convinces Jonathan to go into an elevator at the Waldorf Astoria and pick a floor number. She gets into an adjacent elevator, hoping they’ll choose the same floor. While they do choose the same floor, Jonathan is obstructed by other guests who wish to take the elevator; thus by the time he reaches Sara’s floor, Sara is gone.

Sara’s comically absurd reliance on fate to direct her day-to-day life is central to the progression of the love story being told in Serendipity. But it also serves to divert the viewer’s attention away from a logical resolution to the couple’s search for one another. Surely during their evening out they would have mentioned where they worked or where they lived or where they attended college — any identifying information that could be used to track each other down later on.

Instead viewers are left with two people who are forced to embark on an elaborate search for one another once they realize they are meant to be together. Ultimately, the search is the essence of the long-suffering romantic comedies need — as is pretending the technology to do it more efficiently does not exist.

The Search

In 2001, the capabilities for high-speed internet as we think of it today would not have been available to most Americans. However, dial-up internet service providers like America Online were at their peak, and it would have been a likely recourse for someone like Jonathan, who works in broadcast media, to search for Sara.

But perhaps to bring an element of timelessness to the story, Jonathan begins his search for Sara at Bloomingdale’s, where they first met 7 years ago at a glove display. After realizing that he still has the receipt for the black gloves she purchased all those years ago, Jonathan surmises that he might be able to get information on Sara from her store account number. But the Bloomingdale’s salesman (played by Eugene Levy) is reluctant to give Jonathan any information about the account without first making a commission. Jonathan ends up spending hundreds of dollars on new clothes until the salesman agrees to look up the account, which he discovers has been closed. They must then travel to a warehouse in Queens to search the endless archives for Sara’s original paper application.

Credit: Tapestry Films

Jonathan’s friend Dean (Jeremy Piven) offers the film’s only introspection on the internet. He accompanies Jonathan in his search for Sara, including a visit to her old apartment building, where he encounters a young temp who insists on following the rules at his job. When the temp claims privacy laws prevent him from revealing information about former residents, Dean protests that privacy laws only exist to protect the undeservedly rich. “[These are] kids your age,” he says. “Pimple-faced college drop-outs who have made unhealthy sums of money forming internet companies that create no concrete products, provide no viable services, and still manage to generate profits for all of its lazy day-trading sonofabitch shareholders.”

As a character Dean also helps the film to reassert the importance of long-suffering in a love story that aims to be timeless. Just as the search for Sara comes to a close on a flight to San Francisco, where Jonathan has tracked down Sara’s current address, Dean reveals the real reason he has accompanied Jonathan on his cross-country journey to find Sara: his own marriage has fallen apart. When Jonathan asks why, Dean points to Sara’s resurfaced copy of Love in the Time Of Cholera and says “not enough of this”, perhaps alluding to Florentino Ariza’s five decades-long wait for the love of his life, Fermina, in the novel as well as Jonathan’s unbending passion for Sara after 7 long years.

Fate As Patriarchal Fantasy

Perhaps another reason for Serendipity’s hostility toward the internet is online dating’s democratizing potential when it comes to who does the pursuing in a relationship and the kinds of relationships that can be pursued.

In some ways, Sara’s reliance on fate to guide her romantic life reflects patriarchal attitudes that encourage men to take risks for the women they want while telling women to wait for the right man to come along. From this perspective, Sara’s decision to leave her fiancé and her life in San Francisco to look for Jonathan is not so much about taking control of her love life as it is resigning herself to the man that fate had already picked out for her. As her best friend Eve (Molly Shannon) puts it, clinging to the fairytale of finding Jonathan has kept Sara from accepting the reality that relationships are messy, complicated, and take work.

Credit: Tapestry Films

It is noteworthy that whereas Dean acts a wing man in Jonathan’s search for Sara, Eve is purely the voice of reason in Sara’s quest to find Jonathan. During the trip to New York, Eve barely participates in the search and eventually pushes Sara to admit that the trip was a mistake. That Eve tries to bring Sara down to earth while Dean elevates Jonathan’s romantic fantasies aligns with who the viewer expects to be the chaser and who should allow herself to be chased.

Of course Sara does find the man she has long for for 7 years, just hours after breaking off her engagement and discovering Jonathan has called off his wedding. The couple reunite in the same ice skating park where they had their first date. The snow is falling gently, the stars are bursting with light across the sky, and beyond them the world is standing still. The message, it seems, is that dating apps and websites can’t compete with the organic romance of the nonvirtual world — no matter how hard they try.

But in 2020, questioning the sincerity of love found online is passé. Dating apps and websites are par for the course in search of all sorts of relationships, from simpler encounters (casual sex) to the well-defined serious relationship. Above all, today’s young men and women are far less likely to believe love needs an element of suffering in order to be deep and meaningful.

Ultimately, rom-coms have failed to capture changing cultural attitudes around love and dating in the decades since Serendipity made its debut. The film’s anxieties about the impact the internet would have on the rom-com genre turned out to be legitimate, and there are lingering questions over if and how the genre can be made great again in the era of Tinder.

Twenty-two years ago, the genre made a gamble with You’ve Got Mail. Perhaps what will bring rom-coms back from the grave is the full understanding that they are products of the cultural and technological moments in which they are made; their responsibility is to the present world, not to being timeless.