Jonathan Trager (John Cusack) and Sara Thomas (Kate Beckinsale) met while shopping for gloves in New York. Though buying for their respective lovers, the magic was right and a night of Christmas shopping turned into romance. Jon wanted to explore things further but Sara wasn't sure their love was meant to be. They decided to test fate by splitting up and seeing if destiny brought them back together... Many years later, having lost each other that night, both are engaged to be married. Still, neither can shake the need to give fate one last chance to reunite them. Jon enlists the help of his best man to track down the girl he can't forget starting at the store where they met. Sara asks her new age musician fiance for a break before the wedding and, with her best friend in tow, flies from California to New York hoping destiny will bring her soulmate back. Near-misses and classic Shakespearean confusion bring the two close to meeting a number of times but fate will have the final word on whether it was meant to be.

Bloomingdale's, 1000 3rd Avenue and East 59th Street, Manhattan.

otsoNY Comments: The drink Sara and Jonathan drink at Serendipity 3 is its famous Frozen Hot Chocolate. Also, since the movie opened, the table where they sit has been called the Star Table at the restaurant.

Serendipity III, 225 East 60th Street (btw 2nd and 3rd Avenues) Manhattan.

Serendipity III

Serendipity 3, often written Serendipity III, is a popular restaurant in the Upper East Side of Manhattan founded by Stephen Bruce in 1954. While the restaurant is known for its foot-long hot dogs and frozen drinks, particularly its trademark "Frozen Hot chocolate", it offers a full menu. The restaurant has constantly been ranked as a favorite among Manhattanites, tourists, and celebrities. The gift shop is known for its kitschy novelty gifts.

Serendipity was named after the three legendary princes of the island once known as Serendip (now Sri Lanka), from which the 18th century writer Sir Horace Walpole coined serendipity. Serendipity has been popular since the beginning. Marilyn Monroe frequently patronized the restaurant, Andy Warhol was a regular before he was well-known, and First Lady Jackie was also a frequent guest and once even tried to buy the recipe for the Frrrozen Hot Chocolate for an event she was throwing. Stephen Bruce refused to give her the recipe though he did offer to come and make the frozen drink for her party himself. The recipe can now be found in Sweet Serendipity, a book of recipes and history sold in the general store located inside the restaurant.

East 60th Street (btw 2nd and 3rd Avenues) Manhattan.

otsoNY Comments: Special thanks to Bob Egan for finding this location.

Subway, Park Avenue and East 33rd Street, Manhattan.

Wollman Rink (btw East 62nd & 63rd Street) Central Park, Manhattan.   The ice rink located in Central Park has appeared in several films such as Delirious, Home Alone 2 and My Sassy Girl.

West 56th Street (btw 5th and 6th Avenues) Manhattan.

Park Avenue (btw East 50th and 51st Street) Manhattan.

Waldorf-Astoria Hotel, 301 Park Avenue (btw East 49th & 50th Street) Manhattan.   The hotel is a 47-story, 190.5 m (625 ft) Art Deco landmark, designed by architects Schultze and Weaver and dating from 1931 and was the first hotel to offer room service.

Park Avenue (btw East 50th and 51st Street) Manhattan.

Chelsea Pier 59, 11th Avenue and West 18th Street, Manhattan.

Newark Liberty International Airport, 10 Toler Place, Newark, New Jersey.

otsoNY Comments: Sara's friend catches sight of a street salesman selling fake Prada bags. At this point they are walking along Greene Street very close to Spring Street. As she races across the street, the location actually switches to a street in Canada!

Greene Street and Spring Street, Manhattan.

East 60th Street (btw 2nd and 3rd Avenues) Manhattan.

Waldorf-Astoria Hotel, 301 Park Avenue (btw East 49th & 50th Street) Manhattan.

Central Park (btw 63rd and 64th Streets) Manhattan.

otsoNY Comments: Moments before this scene, Kate Beckensale's character tells the taxi driver to go to number 34 Charles Street, this being the residence of Jonathan Trager, but in fact he lives at number 200 Waverly Place near to Charles Street.

Apartment, 200 Waverly Place (btw West 10th and Charles Street) Manhattan.

Waldorf-Astoria Hotel, 301 Park Avenue (btw East 49th & 50th Street) Manhattan.

Grand Army Plaza and West 58th Street, Manhattan.

Grand Army Plaza

The hotel's main entrance faces the southern portion of Grand Army Plaza; commemorating the Union Army in the Civil War. The section in front of the Plaza Hotel is centered by the Pulitzer Fountain, of Abundance by Karl Bitter, funded by the will of the newspaper publisher Joseph Pulitzer: the statue in the fountain is specifically Pomona, Roman goddess of orchards. The statue was posed for by Doris Doscher, also famous for posing for the Standing Liberty Quarter.

The Mall, Central Park, Manhattan.   A walkway leading to the beautiful Bethesda Terrace, the Central Park Mall runs through the middle of the Park from 66th to 72nd street. It remains the sole formal feature of Olmsted and Vaux's naturalistic creation.

(Near Wollman Rink) Central Park, Manhattan.