With his father gone, Edwin became the man of the household. He tried farming and developed a close relationship with his brother's wife Emma Robinson, who after her husband Herman's death, moved back to Gardiner with her children. She twice rejected marriage proposals from Edwin, after which he permanently left Gardiner. He moved to New York, where he lived as an impoverished poet while cultivating friendships with other writers, artists, and intellectuals. In 1896, he self-published his first book, "The Torrent and the Night Before", paying 100 dollars for 500 copies. Robinson meant it as a surprise for his mother. Days before the copies arrived, his mother died of diphtheria.