Poe was engaged to his teenage girlfriend twice.

Poe married his considerably younger cousin Virginia Clemm when he was twenty-seven, but Virginia wasn't Poe's first engagement ring. This honor belongs to Richmonder Sarah Elmira Royster, who agreed to marry Poe when he proposed to her at the age of fifteen. The young couple never wed (I explain why in The Raven's Tale), but they got back together and renewed their engagement in 1849, just weeks before his passing. Poe and Shelton were neighbors when they were kids and developed a love interest in one another.

When Poe enrolled at University of Virginia and Shelton wed another man, they lost touch. After the passing of Poe's wife Virginia in 1848, they did not converse once more. By that time, Shelton was a widow and Poe took the opportunity to ask her to marry him. She declined, but he continued to pursue her for several months. Poe wrote to his aunt, Muddy, to tell her that the two would be married in October 1849 but he died just ten days before the supposed wedding date arrived.