- Peter Chelsom
- John Cusack as Jonathan Trager
- Kate Beckinsale as Sara Thomas
- Jeremy Piven as Dean Kansky
- Bridget Moynahan as Halley Buchanan
- John Corbett as Lars Hammond
- Molly Shannon as Eve
- 93 mins
Release Date in United States:
Christmas season in New York City, Jonathan Trager (John Cusack) meet Sara Thomas (Kate Beckinsale) at Bloomingdale’s a shopping store in New York were both grabbing for the last pair of black cashmere gloves and find mutual attraction toward each other, and despite they have their own relationship. They spend their day eating ice cream at Serendipity 3, Sara like the name of the ice cream bar Serendipity meaning fortunate accidents, they soon bid farewell and Jonathan wanted to know her contact details but she didn’t give it. While both leaving in their own ways Jonathan forgot his scarf while Sara forgot her pair of gloves that she bought earlier and return to at the ice cream bar and seeing other again. Both consider it is fate that bring them back together again, they decided to go out of town and they go ice skate on Wollman Rink at Central Park were they both discuss their interest and Jonathan talks about Sara freckles on her arms that matches a pattern of Constellation called Cassiopeia, at the end of the night Sara’s write down her contact details after giving to Jonathan it blown away by the wind and he requested another one but Sara tell that fate want them to back out instead she decided let the fate decide their fate by Jonathan writing his contact details on a $5 bill while Sara write her’s in a Book (Love in the Time of Cholera) if fate wanted them back together they surely find their respective things but Jonathan was not satisfied instead they go in a Hotel and each of them enter in a different elevators and see if they both choose the same floor before the elevators doors closes Sara throws one of the gloves and told him her first name. They both press the same floor 23th, but a child gets on the elevator with Jonathan and presses all the buttons and it is too late for him when he reaches the 23th floor and this is where the last time they meet.
Several years had passed, Jonathan soon to be engaged with fiancé Halley Buchanan (Bridget Moynahan) while Sara also is being proposed to her musician boyfriend Lars Hammond (John Corbett). As their wedding dates approaches they find themselves with a cold feet, and decided to find their true feeling of their hearts. Jonathan returns to Bloomingdale’s with his best friend Dean Kansky (Jeremy Piven) to find her information with only a copy of receipt which he found inside the gloves, after getting some information where Sara used to live they lead to a shop near Serendipity 3 where now a bridal shop and Jonathan told Dean that this is a sign to stop looking for Sara. Meanwhile Sara takes her best friend Eve (Molly Shannon) to New York, they gone to many places just by Sara fate to lead them eventually all the places she went to where already been gone by Jonathan without her knowing it. They went to Serendipity 3 to celebrate Eve’s birthday before leaving Eve’s got the $5 bill as a change not knowing it is actually the $5 bill where Jonathan had a name on it. They went to Waldorf Astoria and Eve’s bump into an old friend Halley which is Jonathan fiancé, Halley invited them to attend their wedding rehearsal but Sara got things to do and leave as she returns to her hotel room where she finds Lars, they went to a walk and she sees Cassiopeia in the sky, and breaks her engagement with him.
On the wedding rehearsal Halley had a talk with Jonathan and later Halley’s handed a copy of a book “Love in the Time of Cholera” as a gift where Sara’s had written her name on it. Jonathan and Dean immediately set off to find her, while on the plane Dean confess to Jonathan that he had a problem with his girlfriend and they broke up. They went to Sara’s house and see people intimate and Jonathan fell that it is too late and come back for the wedding. Meanwhile, Sara decided to return home and decided not to attend Eve’s friend wedding. On the plane she finds out that her wallet got exchanged with Eve’s and seeing the $5 bills on it, she get off the plane and search for him, she went to Jonathan’s house and his neighbour tell her that he’s getting married and Sara’s rushes to the Hotel and only see’s a man cleaning the room with her tears running the man told her that the wedding was called off.
Jonathan wandering around the Central Park and he find a jacket where Sara’s forget when she had a walk with Lars. Lying on a skating ground with the jacket as a pillow and the first snowflake drops he sees another pair of gloves flying then he realizes same as he’s pair turn around and sees Sara’s. They formally introduce themselves to each other for the first time and they had their first kiss. The movie ends with them at the Bloomingdale’s enjoying champagne on their anniversary at the same spot where they first met.