Personal life
Dean was a close friend of Arthur Loeb, the son of investment banker John Loeb, a founding partner of the firm Loeb, Rhoades & Co., and Frances Lehman Loeb, a member of the Lehman banking family. Dean met Arthur while they were undergraduates at Harvard, and because he had limited use of his left arm and leg, she worked for him as a typist. The two remained close friends for many years, and although their relationship was platonic, Arthur proposed marriage to her. According to a friend of Dean's, John Loeb offered her money not to marry his son, which she refused, responding, "I won't marry Arthur because I don't want to. But I won't not marry him because you say don't marry him."
In early 1956, Dean gave birth to a son, whom she placed for adoption shortly after his birth. She did not publicly reveal the identity of the child's father, and her friend Arthur Loeb helped cover her expenses during the pregnancy.
Dean had a affair with former investment adviser Rollins Maxwell.
Friends and acquaintances recalled Dean's outspoken personality and heavy drinking. Among her nicknames were "Nurse Dean" and "The Curd of Human Kindness." Abigail Rosen, the first door person at Max's Kansas City, said despite Dean's fearsome reputation, she found her "actually warm." Rosen believed that Dean often made provocative and outrageous remarks because "she wanted to make sure that people didn't think she was ordinary. Being ordinary was the cardinal sin in those days."
Dean met poet Robert Creeley through Mickey Ruskin, the owner of Max's Kansas City. According to poet Gerard Malanga, both Dean and Creeley had been drinking when an exchange between them escalated, and Dean struck Creeley in the face. Despite the incident, Creeley later praised Dean's intelligence and the two became close friends, with Creeley writing a poem inspired by their first encounter.
Bob Russell, a bouncer at Max's Kansas City, said that Dean was infatuated with gay men, particularly a man she nicknamed the "Sugar Plum Fairy," who was referenced in musician Lou Reed's 1972 song "Walk on the Wild Side." Russell recalled that Dean was "often found in leather bars in the West Village in pursuit of the Sugar Plum Fairy. That was her love, and then Lou Reed became the focus of her life."
From 1963 to 1979, Dean lived in an apartment on Morton Street in Greenwich Village.