During the Christmas season in New York City, Jonathan Trager encounters Sara Thomas at Bloomingdale's while they attempt to buy the same pair of black cashmere gloves. They both are in relationships but have a mutual attraction that leads to sharing dessert at Serendipity 3. Sara reveals her opinion that fate determines many of her decisions in life. They encounter each other again when they both have to return to the restaurant to retrieve things that they had left behind. They consider this fate, spend more time together, and then are about to exchange phone numbers. Sara's gets blown into the wind, which she interprets as a bad omen.
She suggests that they put their names and phone numbers out to the universe by putting one on a $5 bill, and the other on the cover of a book that will be sold the next day. If they are meant to be together then each will find the other's item and make contact.
Several years later, Jonathan is in New York City getting engaged to Halley Buchanan. On the same day, Sara is in San Francisco and comes home to find her boyfriend Lars Hammond proposing to her. Cold feet ensues as their respective wedding dates approach; they start their attempt to reconnect.
Sara flies to New York City and her friend Eve persuades her to give up the chase--they go to Serendipity. The $5 bill given to Eve in change has Jonathan's contact information. Jonathan gets as a gift from Halley on the night of the wedding rehearsal the same book that has Sara's phone number. He and his friend Dean fly to San Francisco to find her. Johnathan sees at the airport who he thinks is Sara but is Sara's sister, Caroline. She is fooling around with her boyfriend. Jonathan believes that his chasing ghosts means that he does not want to marry Halley.
On board a plane to return to San Francisco Sara is getting a head set and finds that she has Eve's wallet with the $5 bill of Jonathan. She disembarks and makes her way to his apartment. His neighbors tell her about his wedding at the Waldorf Astoria, and she finds that his wedding has been called off.
Jonathan wanders Central Park, and comes upon a bench at the ice rink in Central park that has a jacket left behind. He uses it for a pillow while lying in the middle of the rink. He has with him one black cashmere glove that he brought along for some reason he does not quite know. He gazes up at the falling snow and a cashmere glove falls on his chest.
He see it is Sara; the jacket is hers. They introduce themselves to each other formally for the first time. Sara and Jonathan are at Bloomingdale's, enjoying champagne on their anniversary at the same spot where they first met.John Cusack as Jonathan Trager
Kate Beckinsale as Sara Thomas
Molly Shannon as Eve
Bridget Moynahan as Halley Buchanan
Jeremy Piven as Dean Kansky
John Corbett as Lars Hammond
Eugene Levy as Bloomingdale's salesman (Macall Polay)
Marcia Bennett as Mrs. Trager
Eve Crawford as Mrs. Buchanan
Evan Neuman as Kenny
Buck Henry (uncredited) as himself
Lucy Gordon as Caroline Mitchell (Sara's sister)
Kevin Rice as Kip Mitchell
Gary Gerbrandt as Josh
Serendipity was shot in New Jersey, New York City, Ontario, and San Francisco, California in the spring of 2001. Following the 9/11 attacks, images of the World Trade Center towers were digitally removed from all skyline shots of New York City.
Serendipity received mixed to positive reviews; based on 130 reviews, the film holds a 58% rating on review aggregator website Rotten Tomatoes. The general consensus states: "Light and charming, Serendipity could benefit from less contrivances." On Metacritic, the film has a 52/100 rating, signifying "mixed or average reviews".
Roger Ebert gave the film 1½ out of 4 stars.
The film opened at #2 at the U.S. box office earning $13,309,241 in its opening weekend, behind Training Day. With an estimated budget of $28 million, this was the first of Chelsom's films to turn a profit. After some of the biggest commercial failures of all time (Town & Country), Serendipity marked the first of several box-office successes for Chelsom, peaking in 2009 with Hannah Montana: The Movie. The film grossed $50,294,317 in the domestic box office and $27,221,987 internationally for a worldwide total of $77,516,304."Never a Day" - Wood
"Moonlight Kiss" - Bap Kennedy
"January Rain" - David Gray
"Waiting in Vain" - Annie Lennox
"The Distance" - Evan & Jaron
"Like Lovers Do" - Heather Nova
"When You Know" - Shawn Colvin
"Black Eyed Dog" - Nick Drake
"Northern Sky" - Nick Drake
"Cool Yule" - Louis Armstrong
"This Year" - Chantal Kreviazuk
"(There's) Always Something There to Remind Me" - Brian Whitman
"'83" - John Mayer
"Fast Forward" - Alan Silvestri
"From Rusholme With Love" - Mint Royale
Not included within the release of the soundtrack"Someone Like You" - Van Morrison
"I'm Still in Love" - CoCo Lee (Asian movie theme song)
"Rose Rouge" - St. Germain