Exterior shots for "How to Lose a Guy in 10 Days" were shot entirely in New York, firmly placing it in one of the most romantic cities in the world. Principal photography began in Greenwich Village, highlighting familiar romantic spots such as the Staten Island Ferry, against the backdrop of the famous New York skyline, and such atmospheric settings as Madison Square Garden and the Manhattan Bridge.
The regal Alexander Hamilton U.S. Customs House in the financial district was transformed into the Astor Museum of Art, scene of the Warren Advertising Agency’s lavish black-tie party. The Conde Naste building at the famed intersection of 42nd and Broadway became home to Composure Magazine, while a loft in Soho was chosen for Ben’s home.
"New Yoik is absolutely one of the stars of this picture," says producer Lynda Obst, a native New Yorker herself. "It’s like no other place on earth, and after September 11th it was thrilling to come back to the city and see the restaurants renewed and people filled with vigor again, determined to live the same life they have always enjoyed. That kind of vitality runs throughout the entire film."
After the two-week shoot in New York, the cast and crew moved to Canada to start filming the interiors, the most exciting of which was the star-studded party full of extras dressed in shimmering gowns and glossy tuxedos. In addition, $15,000,000 worth of Harry Winston diamond jewelry adorned the principals and spilled over in large snifters and bowls. Because of their high value, these shimmering props were guarded by security people who were impossible to distinguish from the actors wearing earplugs and carrying walkie-talkies portraying security people. The dazzling scene was the gala kick-off to the diamond campaign hosted by Warren Advertising. It was also where Andie and Ben discover the truth about their relationship.
While the scene was already a lot of fun to shoot, it really became a treat for everyone when Marvin Hamlisch gave a spontaneous concert of his original songs and Bebe Neuwirth and Robert Klein sung them.
"I walked onto the set and everyone was singing," remembers Obst. "It wasn’t in the script and yet it was one of the most spontaneous moments of movie magic I’ve ever witnessed."
One thing that was very planned, however, was the costuming, and because the two main characters and most of the supporting cast worked either in fashion or in advertising, their clothing had to reflect the contemporary style of their professions. Costume designer Karen Patch, who dressed the cast in "The Royal Tenenbaums," joined Lynda Obst and Kate Hudson in Paris to research and shop, shop, shop.
"We practically devoured thrift stores that had all kinds of fabulous designer clothing," remembers Patch. "Kate has an amazing sense of style and a perfect body for most clothes. She looks great in the new sleek, urban look and the dress she wears at the diamond gala is designed around the 87-carat yellow diamond pendant that was created especially for her by Harry Winston."
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