Jerry Falk (Jason Biggs) is an aspiring writer living in New York City who falls in love at first sight with Amanda (Christina Ricci) and dumps his girlfriend to get with her. Seeking advice, Jerry turns to the aging struggling artist who acts as his oracle -- and that includes trying to help sort out Jerry's romantic life.

Reservoir Bridge Central Park (West 94th Street) Manhattan.   Reservoir Gothic Bridge The Gothic Bridge in Central Park is one of three cast iron bridges around the Reservoir. Built to carry recreational equestrian traffic in the park, as well as pedestrians. The triangular spaces at each end of Gothic Bridge (called spandrels) were given curved ironwork suggestive of Gothic church architecture of the Middle Ages, hence the bridge's name. The graceful curves and oval vault make Gothic one of the most distinctive bridges in the park. No two bridges in Central Park are the same.

Greywacke Arch, Central Park, Manhattan.

Isabella's Restaurant, 359 Columbus Avenue and West 77th Street, Manhattan.

Stage Deli, 834 7th Avenue and West 53rd Street, Manhattan.

Jerry Falk's Apartment, 52 East 82nd Street and Park Avenue, Manhattan.

Charles Street and Bleecker Street, Greenwich Village, Manhattan.

Les Pierre Antiques, 369 Bleecker Street and Charles Street, Manhattan.

East River, near Queensboro Bridge, Manhattan.

H B Studio Inc, 120 Bank Street and Greenwich Street, Manhattan.

Quad Cinema, 34 West 13th Street (btw 5th and 6th Avenues) Manhattan.

Brownstone, 441 East 87th Street (btw 1st Avenue & York Avenue) Manhattan.

Sant Ambroeus Restaurant, 1000 Madison Avenue and East 78th Street, Manhattan.

Madison Avenue and East 78th Street, Manhattan.