In the late 1960s, smart yet naïve misfit Ann Workman is in search of an education and the “Real Thing”—to be in love with someone who loves her equally. Then Jimmy appears, as if by magic. A misfit like Ann, Jimmy is a rebel who rejects his upper-class Midwestern upbringing. Many years later, Ann recalls this time of innocence—and her own obsession with Jimmy. She tries to imagine where she might be if she had chosen differently all those years ago. What if she had gone to Stanford University, instead of a small school on the East Coast? Would she have been caught up in the Summer of Love and its subsequent dark turns? Or would her own good sense have saved her from disaster? Dear Ann captures how consideration of the road not taken can illuminate, and perhaps overtake, our present.