Every now and then, a movie comes along that you can't help but kick yourself for liking. Like purchasing a CD of '80s super-hits off a late-night infomercial, watching "Serendipity" leaves you feeling somewhat violated but no less delighted at the trespass.
A self-effacing romantic comedy of the highest (or is it lowest?) order, the film sets out to reunite a pair of star-crossed lovers over the course of a madcap weekend of near misses and benevolent signs. John Cusack (lovable even as a narcissistic man-child in "High Fidelity") plays Jonathan Trager, a Manhattanite who has a chance encounter with a beautiful Brit named Sara (Kate Beckinsdale). After grabbing for the same pair of cashmere gloves at Bloomingdales, the pair decide to share a cup of joe at a cute java shop named (wouldn't you guess?) Serendipity. He asks for her number. She responds by saying she believes in destiny. In other words, if they're meant to be together, circumstance will make it so.
After a trip to the Central Park skating rink and some dazzling conversation -- any guy who can spot a satellite in a girl's freckles is a keeper -- she's passing her number along. But in the exchange, the scrap slips out of his hands and she becomes convinced it's a sign. Sara then concocts a ridiculous scheme in which she writes her name and number on the inside of a book (to sell the following day) and he writes his digits on a $5 bill that she quickly sends into circulation by purchasing breath mints at the local bodega.
A few years later, she's engaged, he's about to get married, and both set out on one last attempt to find the other. With their best friends in tow (Jeremy Piven for him, Molly Shannon for her), the two embark on a New York weekend in which fate seems to be pushing them together only to ensure they never quite make it. She'll jump into a cab just as he's walking by on the street, and so on. The most ridiculous of these scenarios occurs when Sara, sitting on a bench, accidentally touches a wadded-up piece of gum -- the very one Jonathan had stuck there hours earlier.
Perhaps the most ironic thing about "Serendipity" is the way it undercuts the only genuine idea it possesses. Challenging the illogic of Sara's fate-based belief system, Molly Shannon's Eve reminds her friend that life is about making decisions, not following some romanticized game of chance. That sobering dose of truth has no place in a film that is, in fact, one big romanticized game of chance.