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While the story "Where Are You Going? Where Have You Been?" is told by a third-person narrator, there are times in which Connie's point of view is used. For instance, in the exposition, Connie's view of her mother is discussed,
Now her looks were gone, and that was why she was always getting after Connie.
But, Connie "knew she was right at that moment," she thinks one time her mother scolds her. "She knew she was pretty and that was everything." This selfish perspective of Connie interspersed with the third-person narrator's and the fact that "her mind was all filled with trashy daydreams" along with her confusion between reality and appearance--"Everything about her had two sides to it"--contribute to an ambiguity in the story. Added to this, the story has no definitive resolution, so there does seem to be a dream-like quality to the narrative.
Of course, there are also two sides to Arnold Friend, whose name can spell "An old Fiend" if the r's are removed from it. At first, Connie perceives Arnold as a young, hip man; however, his confusion with what slang is current and his appearance of wearing makeup and a wig to hide his age further the unreality of the situations in Oates's narrative. That he seems to be balancing himself in boots that are too large suggests that Arnold is hoofed, like the devil. Certainly, Arnold's ability to control Connie's young mind, terrorizing her, suggests the power of a devil.
Because Oates's initial title was "Death and the Maiden," some critics feel that the story is an allegory. As such, Arnold Friend can certainly play the role of the tempting, duplicitous devil. Or, he can simply represent the duplicity of Connie and be one of her trashy daydreams that have gone a bit too far psychologically. Thus, her standing at the door before she opens it to accompany Arnold Friend represents her realization that she has lost any girlish innocence that she may have had:
She watched herself push the door slowly open as if she were safe back somewhere in the other doorway, watching this body and this head of long hair moving out into the sunlight where Arnold Friend waited.
'My sweet little blue-eyed girl,' he said, in a half-sung sigh that had nothing to do with her brown eyes....
Connie has lost the one side of her--her 'blue-eyed' innocence. Now she is consumed by the evil side with which she originally just flirted; now it is
on all sides of him [Arnold], so much land that Connie had never seen before and did no recognize except to know that she was going to it.
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