Randy Jensen (Molly Ringwald) is a smart, independent tour guide who beats womaniser Jack Jericho (Robert Downey Jr.) at his own game. After a quick fling, her indifference only causes him to become smitten with her. Randy is too busy for romance, trying to keep her alcoholic gambler father, Flash Jensen, out of harm's way. Jack's persistence soon pays off when he offers to help rescue Randy's dad from the mob.

Columbus Avenue (btw West 74th and 75th Streets) Manhattan.

Columbus Avenue and West 75th Street, Manhattan.

Jack’s Brownstone, 43 West 73rd Street and Columbus Avenue, Manhattan.

West 73rd Street and Columbus Avenue, Manhattan.

Columbus Avenue (btw West 73rd and 74th Streets) Manhattan.

Cherry Hill, Central Park, Manhattan.

Natural History Museum, Central Park West and 79th Street, Manhattan.