Kate (Jennifer Aniston) is struggling in the advertising business in New York, believing in her talents, but she cannot move forward. When the chance comes for her to get promoted, her boss (Kevin Dunn) decides to pass her up because she is 'not stable enough'. Her co-worker Darcy then makes up a story about an engagement with a guy called Nick (Jay Mohr) who lives in Massachusetts, and works as a freelance videographer, with whom Kate had her picture taken during a recent friends' wedding. All seems to work out well for Kate. She even gets the attention of a colleague (Kevin Bacon) she had always wanted, but then events take a dramatic turn forcing her to bring her alleged fiancé to dinner with her boss after Nick saves a little girl from a fire and winds up on the news, not to mention on the cover of several newspapers. She asks Nick to make a fool out of himself and to "break up" with her. Nick doesn't want to comply, but he cooperates to please Kate. Nick and Kate slowly but surely start to fall in love.

Bus Stop, East 42nd Street (btw Madison Avenue and Park Avenue) Manhattan.

Times Square (Broadway, 7th Avenue, West 42nd and 47th Streets) Manhattan.

Elks Lodge, 1005 Washington Street, Hoboken, New Jersey.

New York Public Library, 476 5th Avenue (btw East 40th and 42nd Streets) Manhattan.

Rooftop, 437 Madison Avenue (btw East 49th and 50th Streets) Manhattan.

8th Avenue (btw West 21st and 22nd Streets) Manhattan.

Restaurant, 150 Central Park South (btw 6th and 7th Avenues) Manhattan.

Kate's Apartment, 301 West 21st Street (btw 8th and 9th Avenues) Manhattan.

West 21st Street and 8th Avenue, Manhattan.