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Yes, it was in one of the scenes where the staff were "dirty dancing" in their quarters.
"Be My Baby" by The Ronettes is the first song in the movie Dirty Dancing (1987).
No, they never dated.
Jack Weston played Max Kellerman
In the movie Dirty Dancing, Penny becomes pregnant after her and Robbie have sex. Penny was played by Cynthia Rhodes and Robbie by Max Cantor.