Joyce Carol Oates dedicated "Where Are You Going, Where Have You Been?" to Bob Dylan, saying that she wrote the story after listening to his song "It's All Over Now, Baby Blue." The story was further inspired after Oates read a story in Life about Charles Schmid, a serial murderer in the Tucson area.
Schmid and Arnold Friend share several similarities. Schmid stuffed rags into his leather boots to make himself appear taller; Connie notices that Arnold Friend wobbles in his boots frequently and suspects that his feet don't go all the way to the bottom. Schmid wore pancake makeup and dyed his hair black, which also reflects the imagery of Arnold Friend. Schmid also bragged about sexualizing young women, bragging that he'd taught women "one hundred ways to make love." Arnold Friend brags that he is going to teach Connie how to be his lover, clearly using sex as a means of control:
I'll tell you how it is, I'm always nice at first, the first time. I'll hold you so tight you won't think you have to try to get away or pretend anything because you'll know you can't.
One of the most captivating aspects of Schmid's story is that numerous teenagers knew about his crimes and none of them told on him. He seemingly exerted such an influence over them that they believed that "telling would just have made it tough on everyone." Arnold Friend exerts a similar sense of supernatural mind control over Connie, and Ellie Oscar travels with Arnold Friend, but there is no indication that he will ever break Arnold Friend's trust.
"Where Are You Going, Where Have You Been?" is thus inspired by an actual serial murderer's crimes, but Connie and Arnold Friend are fictitious creations.