[3] In 1968, she resigned from her job as a secretary in the Dutch consulate in New York City to become a call girl,[1] making up to US$1,000 a night (equivalent to $8,800 in 2023).

for the Canadian GRT Records label (GRT 9230-1033), on which she discussed her philosophy regarding sex and prostitution, sang a cover version of the Beatles' song "Michelle", and recorded several simulated sexual encounters, including an example of phone sex, a threesome, and a celebrity encounter with guest "vocal" by Ronnie Hawkins.

[8] For several years in the 1970s, Hollander lived in Toronto, where she married Frank Applebaum, a Canadian antique dealer, and was a regular fixture on the downtown scene.

She mentioned a lover named John Drummond, with whom she partnered for many years, co-authoring two books, including Let's Get Moving (1988) about their life together: "I went there with, who for years had been the love of my life, John Drummond, a wild Scottish intellectual who, at times, liked his whisky, beer, and wines too much.

": "The love of my life, 25 years ago, John Drummond, a brilliant and boisterous Scotsman with a 'Thatcheresque' accent had, especially under the influence of a few scotches, beers, or wine, become quite destructive towards me.

[10] Hollander claimed to have "turned gay" around 1997, establishing a long-term relationship with a Dutch poet called Dia.