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Songs That Ask a Question.
Robert Goulet "Come Back To Me
Where Have All The Flowers Gone - Brothers Four
Ray Conniff - BESAME MUCHO (KISS ME A LOT)
Yul Brynner and Deborah Kerr perform "Shall We Dance" from The King and I
What More Can a Woman Do?
Where Do The Children Play? - Cat Stevens
Andy Williams-Speak Softly Love? (Lyrics)
Brother, can you spare a dime? - George Michael
Ella Fitzgerald - Skylark
Stay One More Night - Chris Norman - Lyrics
Shirley Bassey - You Don't Bring Me Flowers? (Duet w/ Robert Goulet)
Doesn't anybody stay together anymore?
Not a song that asks a question I know, but I just love the song. 
What's So Funny About Peace, Love and Understanding?
Engelbert Humperdinck - How I Love You
This one asks many questions.