Serendipity (2001)

There is a moment early in Serendipity (2001) where John Cusack's character, Jonathan Trager, watches a woman he has known for exactly one evening get into a cab and disappear into the New York night. He had her number. He let her write it on a five-dollar bill and spend it. He stood there and let her go. The film spends its next 90 minutes asking whether two people destined for each other will find their way back. It's a ridiculous premise, and it works almost entirely because Cusack and Kate Beckinsale are very good at making ridiculous premises feel true.

The Setup: Christmas Shopping as Fate

Jonathan and Sara meet at Bloomingdale's during the holiday rush, both reaching for the same pair of black cashmere gloves. They end up spending the evening together: hot chocolate at Serendipity 3 on the Upper East Side, ice skating at Wollman Rink in Central Park. Then Sara, who believes strongly in signs from the universe, proposes a test. She writes her phone number inside a copy of Gabriel Garcia Marquez's Love in the Time of Cholera and sends it to a used bookshop. Jonathan writes his number on a five-dollar bill and releases it into circulation. If they're meant to be, the universe will arrange a reunion. Years later, with both of them engaged to other people, they're still looking.

The film is not really a love story between two people. It's a love story between two people and the idea of fate. Director Peter Chelsom shot the New York sequences in summer 2000, using 350 extras in winter coats at Wollman Rink during August to fake a December evening. It shows a lot of deliberate effort to construct something that feels effortless.

What the Cast Actually Does

Cusack had already done Say Anything (1989) and High Fidelity (2000), both films where standing in the rain with your feelings exposed was essentially the job description. He was very good at this. In Serendipity, he plays a man whose entire life is organized around a single night he can't forget, and Cusack plays that obsession with just enough self-awareness to stop Jonathan from becoming pathetic. The script by Marc Klein does not give him much help. Cusack does it himself.

Beckinsale is sharper than the film deserves. Sara is written as a muse, the one who sets the rules and disappears, and a lesser performance would leave her feeling like a plot device. Beckinsale gives Sara a particular kind of British certainty, the confidence of someone who genuinely believes she has figured out how the universe works. When she says "I think that on some level you knew this couldn't be forced into happening," you believe she means it. That matters more than it sounds.

Jeremy Piven, playing Jonathan's best friend Dean, is doing his best Jeremy Piven impression: fast-talking, sardonic, exasperated by his friend's romantic decisions. He and Cusack were close friends in real life, having attended high school together at The Piven Theatre Workshop in Evanston, Illinois, which is why their scenes together have a lived-in ease that the film's central romance sometimes lacks. John Corbett shows up as Sara's fiance Lars, a new-age musician whose only job is to be likable enough that you feel slightly bad when Sara abandons him for a stranger she met five years ago. Corbett handles this with grace. Molly Shannon plays Sara's best friend in full comic relief mode, and she finds the jokes in scenes that don't quite have jokes written into them.

A Film That Almost Wasn't Released

The movie opened on October 5, 2001, less than a month after the September 11 attacks. The studio seriously considered shelving it. New York City skyline shots that included the World Trade Center towers were digitally altered to remove them before the film's release. Miramax chose to proceed, and the film earned $77.5 million worldwide against a $28 million budget. For director Peter Chelsom, who had come off a string of commercially unsuccessful films including Town & Country (2001), it was the first film he had directed that turned a clear profit.

The timing is worth noting because the film's central belief, that the universe has a plan and that good things are coming if you trust the signs, landed differently in October 2001 than it might have in, say, July. For many people it was exactly the kind of movie they needed to see, or exactly the kind of movie they couldn't stomach. Both reactions make sense.

Is Serendipity a Christmas Movie?

The Christmas connection is real but partial. The opening act is thoroughly embedded in the holiday season: department store crowds, holiday shopping, winter coats, frozen hot chocolate, ice skating under the Manhattan skyline. The Serendipity 3 restaurant scenes feel like a Christmas movie. The rest of the film takes place mostly in summer and fall flashback, with the final act set during a New York winter that's less specifically Christmas and more generically cold.

Call it a Christmas-adjacent movie. The holiday gives the story its texture and its first-act warmth. The inciting meeting could not happen in quite the same way in August. But the film doesn't sustain its Christmas energy through the full runtime the way Home Alone or The Holiday do. It's a winter movie that happens to open at Christmas.

The Serendipity 3 restaurant, which still operates on East 60th Street in Manhattan, dubbed the table where Jonathan and Sara drank their Frozen Hot Chocolates "the Star Table" after the film's release. People still request it specifically.