Edgar A. Poe’s short-lived but theatrical relationship with Providence poet Sarah Helen Whitman has been treated extensively by Poe scholars. These studies, while varied in scope and approach, typically bend their energies toward pinpointing the precise reasons why this relationship, though in many ways an ideal union of intellectual interest and sympathetic genius, nevertheless adopted a downward trajectory, ultimately imploding into estrangement just prior to the poets’ proposed marriage. Some scholars, following suit from Poe, have placed the blame for the relationship’s disastrous collapse on Whitman’s mother, who expressed disapproval of Poe’s character throughout the relationship. Other scholars identify Poe’s own flagrant breach of a temperance vow he had undertaken at Whitman’s behest as the cause of the couple’s falling out. In distinction from these views, this chapter suggests that, as significant as these factors were, they form only part of the fissure at the foundation of Whitman and Poe’s romance. It further asserts that a more fundamental source of tension between the two minds may be found in each’s forceful and contradictory attitudes toward the multiple interpersonal, literary, and critical spaces of “Boston.” Accordingly, this chapter pursues a reading of the Poe–Whitman courtship against the backdrop of their individual encounters with Bostonian spaces, ultimately tracing the hitherto overlooked role those spatial influences performed within the collapse of the Poe–Whitman relationship.