Jack (Philip Seymour Hoffman) is a shy and awkward man who drives a limo and lives an unassuming life. His friend and co-worker, Clyde (John Ortiz), and his wife Lucy (Daphne Rubin-Vega), feel sorry for Jack and set him up on a blind date with Connie (Amy Ryan). Connie shares Jack's shyness and awkwardness, but through each other they seem to be able to find solace within themselves. Trouble might be brewing in paradise though, as Clyde and Lucy's marriage stumbles just as Jack and Connie's relationship grows.

Christian Dior Store, 870 Madison Avenue and East 71st 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.

Bethesda Terrace, (Mid-Park at 72nd Street) Central Park, Manhattan.

Boating Lake, Central Park, Manhattan.

Lucy’s Apartment, 439 West 46th Street (btw 9th and 10th Avenue) Manhattan.