No, they never dated.
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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).
Jack Weston played Max Kellerman
Dirty Dancing, The Sandlot, Endless Summer
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.