In the crossword puzzle, the clue for 16 across is "1964 Oscar winning song." The answer is "Chim Chim Cher-ee," the song that Dick Van Dyke made famous as Bert in Mary Poppins (1964). The long answer in the middle of the puzzle is "Bye Bye Blackbird"; he was also in the movie Bye Bye Birdie (1963).
The actress playing Carol is actually Stacey van Dyck, daughter of Dick van Dyck and sister of Barry van Dyck.