My Sassy Girl is the tale of the first and last time Charlie Bello (Jesse Bradford) falls in love. From their initial meeting, trouble is the name of the game. Imagine an amorphous mass of dating disasters and you get an idea of the relationship btw the young couple. Some mysterious force with the strength of gravity btw two planets must be at play btw Charlie and Jordan (Elisha Cuthbert) as the relationship truly makes no sense on the surface. Everything seems pitted against the two of them. Things suddenly come to a halt when the two write letters confessing their love for each other. Agreeing to meet a year later to read the love letters together, Charlie and Jordan go their separate ways.

Brooklyn Bridge, Lower East Side, Manhattan.

Washington Square Park, Greenwich Village, Manhattan.

Umpire Rock, South Central Park (btw 61st and 62nd Streets) Manhattan.

Cherry Hill, Central Park, Manhattan.

Wollman Rink (btw East 62nd & 63rd Streets) Central Park, Manhattan.

Subway, East 42nd Street and Park Avenue, Manhattan.

Subway Exit, East 23rd Street and Broadway, Manhattan.

Pine Bank Arch, Central Park, Manhattan.

The Mall, Central Park, Manhattan.

Roark Office, 7 East 78th Street and 5th Avenue, Manhattan.

Roark's Townhouse, 5 East 78th Street and 5th Avenue, Manhattan.