Innitially through letters and eventually through conversations they shared on their strolls through the cemetery and the Athaneum, the two discussed poetry, thoughts on literary criticism and more. Poe also began a long series of declarations of love and a myriad of marriage proposals only to be refused by the beautiful Mrs. Whitman. Why refusals while their commonalities generated such emotion? It was obvious that the similarities in character between Poe and Whitman were unfortunately not enough to keep the "incandescent fire" ("Arcturis" - Whitman) of their love burning. Poe's impulsiveness, uncontrollable fits of rage, and alcohol abuse were too much for Sarah to handle. More difficult to handle were the constant reminders from Poe's many enemies who, out of concern for their friend warned Sarah of his alcoholism and horrifying behavior under its influence. Poe of course believed that these informants came from literary circles; writers and critics that he himself had criticized and denounced in papers and lectures.

"My heart is heavy, Helen, for I see that your friends are not my own."

People were not only talking about Poe's drinking but stories were rampant among circles that he was also looking to unburden himself financially through Sarah's inheritance. Even the famous orator, Horace Greeley, who had loaned Poe a small amount of money and hadn't been repaid came forward to warn Sarah of Poe's shortcomings. Upon hearing this and observing the lack of balance in Poe's nature, Sarah's mother also showed concern for her daughter. Afraid that the relationship would continue and that an engagement was inevitable, she had papers drawn to insure that Poe would not be able to capitalize on Sarah's wealth in the event that she should die before him.

Sarah's indecisiveness in response to Edgar's incessant marriage proposals was more than enough to ignite his addiction to alcohol. Ironically, however, this excessive behavior was one of the characteristics that kept Mrs. Whitman undecided. She often pleaded with him to end his abuses, whereupon Edgar would promise on his love for her. Within days Sarah would be informed of yet another drunken outburst. Once, while Poe was in Lowell, Massachussetts, on a lecturing tour, Poe's despair in his relationship with Sarah caused him to attempt suicide. Poe, however only took half the dosage of laudanum it would have taken to accomplish his death. He became violently ill and after a long recovery once again pursued his love, his Helen. The worst of these episodes occured after another of Mrs. Whitman's refusals. So overcome with sorrow, loneliness and despair, Poe took to the bar in his hotel. He made his way to 76 Benefit Street, the home of his beloved Sarah, where he ranted and raved so uncontrollably that it took Sarah's mother 2 hours to convince her to greet their guest. Although she had been discouraging her daughter's affair with the man from Richmond, she was now encouraging her to accept his proposal simply to calm him down long enough to get him to a doctor. This Sarah did, once again with the condition that he stop his excessive drinking. This would be Poe's last chance with his lovely Helen.

The story goes that the day of the nuptuals had finally arrived. Once again, Sarah would be told that on the morning of his wedding to his beautiful Helen, Poe would be seen drunk in the bar of his hotel. Edgar arrived at Sarah's home to plead forgiveness.

"as they looked into each other's eyes, the inner conflict in the soul of each was all at once made clear.
She knew that he had fought and lost. He knew that 'the Helen of a thousand dreams' must ever be a dream to him"

Sarah then put her ether-doused handkerchief to her face in hopes of passing out from its effects. Poe left Sarah, but not without declaring his love for her one last time.