"Where Are You Going, Where Have You Been?" tells the story of Connie, a fifteen year old with a strained relationship at home with her parents. She often goes with her girl friends to hang out at the local shopping center, but on occasion, the girls sneak over to the local drive-in to hang out with older boys.
On one of these nights at the drive-in, Connie catches the eye of a strange boy she's never seen before. He gives Connie an appreciative look.
Later that summer on a Sunday, Connie's family prepares to go to a barbecue. Connie refuses to go and stays home. As she's sitting in the backyard daydreaming, she hears a car pull up. It's the interesting boy from the drive-in and he has a friend with him. The boy introduces himself as 'Arnold Friend' and his sidekick as Ellie.
Arnold invites Connie to go for a car ride with him. He shows off the car to her, hoping to entire her, but Connie is wary of him, thinking it strange that she's never seen him before or does not know anything about him. Connie also begins to notice certain oddities about Arnold, like the fact that his hair seems like a wig, or his face is mask like or painted on, and his feet wobble in his tall boots. Feeling suspicious, Connie politely, then not so politely, declines, but Arnold will not have 'no' for an answer. He begins to come across as very threatening to Connie, and she becomes frightened. She wants to call the police, but Friend threatens her not to do it, or he'll come inside the house to stop her. Ultimately, Friend also threatens the safety of Connie's family if she refuses to go with him, so at last she relents.
The story ends with Connie pushes the screen door open to join Arnold Friend outside.