Serendipity Is the Rom-Com Gift That Keeps on Giving

By Ashley Morton


Romantic comedies are generally not considered the highest form of filmmaking, and many of them come and go without much ceremony. But every so often audiences find a gem to cling to, and 2001’s Serendipity featuring John Cusack and Kate Beckinsale, is just such a one.

New York City during the holiday season is a magical place. Decked-out windows, ice skating, outdoor markets — the city is giddy with joy and potential. Still, in a city bustling with strangers, you’re more likely to wish the person you bump into doesn’t curse you out, much less be “the one.” But this is how Serendipity begins, in a New York department store shortly before Christmas, when two attractive young people reach for the same pair of gloves.

Cusack’s character, Jonathan, is immediately smitten, but Sara (Beckinsale) is a believer in signs, so it isn’t until the two cross paths for a second time that evening that she allows her (not single!) self to really spend time with him. But rom-com love is never simple, and Sara cannot let go of the idea that the timing of the meeting might be off. So she puts it to a test, and the test — to everyone’s disappointment — fails. Years later, both Sara (now living in San Francisco) and Jonathan are attached to other people (played by John Corbett, and Bridget Moynahan respectively, in a nice bit of scorned lovers of Sex and the City casting) but still wondering about their failed encounter.

Even though the stars spend little screen time together, their moments together are undeniably watchable. The appeal of Jonathan’s enchantment with Sara never wears off. By bringing back a little of his Lloyd Dobler (Say Anything) twinkle-eyed and ruffled-hair charm, Cusack manages to keep Jonathan attractive and likable, despite the fact that he’s behaving a bit like “a jackass” (to quote the film).

Better known for her action-oriented roles, Beckinsale, meanwhile, is lovely and approachable. Her performance feels utterly sincere, even when she’s watching Lars (Corbett), her New Age musician fiancé try to sexily play a shehnai.

We don’t just root for Jonathan and Sara to find one another, we also feel pain they lost so much time to be together. Every near-miss is a moment of frustration. For any person who’s ever had a “what if” scenario, the pair’s connection feels cathartic, and, ultimately, meant to be.