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Serendipity Is the Best Christmas Romance. Take That, Hallmark!

You can watch all the small-time Christmas romances you want, but I’ll sit over here and watch Serendipity. Serendipity is the best Christmas romance movie, and I’ll stand by that forever. It’s a rom-com with better actors than your Hallmark fare, and without the bedraggled city woman who needs to move to a small town to find love. In this movie, love is right where it belongs: in New York City.

Serendipity is a rom-com where the leads end up together, so me telling you the plot isn’t really going to spoil it. Jonathan Trager (played by John Cusack – hello?!? We’re already starting off on a good foot) meets Sara Thomas (played by Kate Beckinsale – totally cute couple, right?) at Bloomingdale’s in Manhattan. It’s five days before Christmas, and they both reach for the same pair of black cashmere gloves. There’s banter, there’s tension, and there’s chemistry before he lets her buy the gloves and agrees to go with her to Serendipity, a real-life confectionery cafe that she chose because she liked the name.

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We learn, here, that Sara believes in serendipity. In happy accidents and fate bringing people together. “I think fate’s behind everything,” she tells Jonathan. “[Fate] sends us little signs, and it’s how we read the signs that determines whether we’re happy or not.” So, even though fate put Sara and Jonathan together, they are both involved with other people, and that’s the sign that they’re not supposed to be together. 

But, Jonathan and Sara realize that they like each other very much. So there’s frozen hot chocolates and some ice skating, after which Sara convinces Jonathan to take a chance with fate. They both write their full names and phone numbers on objects – his on a $5 bill, hers in a book (Love in the Time of Cholera by Gabriel Garcia Marquez) that Sara sends out into the universe, convinced that if they’re meant to be together, fate will bring these objects back to them, proving that they are soulmates. They split the pair of gloves, then part, leaving fate to chance. It’s Christmas romance magic!

The twist here is that they each spend six years turning over fivers and looking in books, all the while agreeing to marry other people. Then, three days before Jonathan’s wedding, and a week before Sara’s, the universe conspires to bring Sara and Jonathan together, back in New York City, at the location of their first ice skating date.

Here, I must confess that I’m a little like Sara. I believe in signs and predestiny. I believe that the great loves of our lives are fated, and that God or the universe or whoever, will bring people together when they’re meant to be together. I’ve seen it happen in my own love life, so it clearly must be true.

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My partner, Mike, is the love of my life. We met on a dating app when I was 48 and he was 50, which doesn’t sound like serendipity, but when you consider how many people there are on those things, it really is kind of magical to actually meet someone that you like. The thing about Mike and me is that we went to college together, a small college where we could easily have known each other, but didn’t. Then we both moved to New York, he got married, and we spent the next 20 years circling around each other, with mutual friends and work colleagues in common, but never meeting. Not even on Facebook. We even went to the same 50-person wedding, where the groom was his best friend and the bride was one of my closest friends. We were both there with other people. Never saw each other. Our Bumble meeting was two years later, after his divorce, and after I’d done a lot of work on myself and my relationship to relationships. By then, we were both ready, and still living in New York City.

So, you can see why I like Serendipity. The action of the movie centers around Jonathan’s and Sara’s searches for each other, with just as many near-misses as I had with my partner. And these almost-meetings take place all over Manhattan, with classic New York City foibles. Jonathan’s best man and best friend, Dean (played by Cusack’s real-life bestie at the time, Jeremy Piven) uses his connections as an obit writer for The New York Times to track down Sara’s whereabouts.

They start at Bloomingdale’s, after Jon finds the glove receipt with Sara’s credit card number. Quite possibly the best part of the movie comes at Bloomie’s: a crotchety, rules-following sales clerk, played by Eugene Levy, who agrees to help them if Jon buys a suit from him. Eugene Levy is comedy gold, putting more com in this Christmas rom-com. 

As Jonathan and Dean cross the city on a wild goose chase for Sara’s current address, Sara is crossing Manhattan, minutes behind her erstwhile love, with her best friend, Eve. Molly Shannon plays Eve. This movie is packed with comedy hard-hitters to go along with its gorgeously relatable leading cast. 

Even though the movie’s wild-goose chase doesn’t take place at Christmastime, it is the most magical part of the movie. And magic is what we want in a Christmas romance. Jonathan spends the morning at Chelsea Piers, and Sara gets there later, encountering a piece of gum Jonathan had stuck to a bench hours before. Okay, that’s pretty gross. But the point is, how random is it that this couple would sit on the same bench?

Later that day, Jonathan and Dean make their way to the restaurant Serendipity, but walk away from it just as Sara and Eve are pulling up in a cab. They’re right next to each other, and we’re wishing for a meeting… but no. Still, they’re getting closer and closer as the day gets longer. The magic is in the rooting for them, in the rooting for fate, or serendipity, to bring the cute couple together where they belong. 

Unfortunately, or fortunately, Sara and Jonathan do not see each other again until they’ve both called off their respective weddings. Both lovers realize that the idea of one another is as appealing as the person themselves. And if you’re chasing the idea of another person, you probably shouldn’t be getting married. Only then does Jon find Sara’s number in a copy of Love in the Time of Cholera, while Sara finds the five dollar bill with Jon’s phone number. This is their final sign, the last twist of fate that proves they were meant to be together. Of course there’s a twist, which I won’t reveal here, because this movie has great moments that don’t deserve to be spoiled.

Serendipity shows us that Christmas romance is possible in New York City, even when shopkeepers and the wrong fiancés conspire to thwart its progress. So take the subway home, get yourself some frozen hot chocolate, and post up on the sofa to watch this delightfully romantic and magical film. I plan to watch it at least four more times, and to remember that true love is sometimes a matter of fate.

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Written By

Tracey Lynn Lloyd has been a writer, a marketer, and a sarcastic smartypants. She has a BA from Yale, and an MBA from Duke, even though she couldn't tell you anything about finance. She lives in Brooklyn, NY with her father and her cat, all of whom fight for control of the keyboard.

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