Per The Guardian, Donaldson was an English writer best known for his satirical book "The Henry Root Letters." An article from The Sunday Times adds that he was an eccentric and wealthy man. Donaldson had a wild life that was brimming with drugs, women, and chaos. At one point, Donaldson worked with Bob Dylan and he also published some of Sylvia Plath's early work (per Terrence Blacker). As for his relationship with Simon, the pair reportedly met sometime in the 1960s when Simon visited London in her 20s. He later said (via The Guardian) that Simon was "the answer to any sane man's prayers; funny, quick, erotic, extravagantly talented".

Simon on the other hand stated that Donaldson was "a sardonic, adorable, long-legged, coffee-scented charmer" (per the Daily Mail). According to The Sunday Times, Simon and Donaldson had an intense connection. So much so that Donaldson began referring to Simon as "the next Mrs. Donaldson" only six weeks after their relationship began. It seems that Simon was all for moving to England and marrying Donaldson, whom The Guardian notes had already been married twice before. Nevertheless, Simon and Donaldson never made it to the aisle. It's believed that Donaldson left Simon for actress Sarah Miles. He broke off their relationship via a letter. 

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