Hart was born Pearl Taylor in the Canadian village of Lindsay, Ontario.
Her parents were both religious and affluent, those provided their daughter with the best available education.
At the age of 16, she was enrolled in a boarding school where she became enamored with a young man, named Hart, who has been variously described as a rake, drunkard, and/or gambler.
The two of them eloped, but Hart soon discovered that her new husband was abusive and left him to return to her mother.

Hart reconciled with and left her husband several times.
During their time together they had two children, a boy and a girl, whom Hart sent to her mother who was then living in Ohio.
In 1893, the couple attended the Chicago World's Fair, where he worked for a time as a midway barker.
She in turn developed a fascination with the cowboy lifestyle while watching Buffalo Bill's Wild West Show.
At the end of the Fair, Hart left her husband again on a train bound for Trinidad, Colorado, possibly in the company of a piano player named Dan Bandman.

Hart described this period of her life thus: "I was only twenty-two years old.
I was good-looking, desperate, discouraged, and ready for anything that might come.
I do not care to dwell on this period of my life.
It is sufficient to say that I went from one city to another until some time later I arrived in Phoenix".
During this time Hart worked as a cook and singer, possibly supplementing her income as a demimondaine (prostitute).
There are also reports she developed a fondness for cigars, liquor, and morphine during this time.

A story of this period claims that while in Phoenix, Hart ran into her husband.
He convinced her to come back to him and move to Tucson.
Once the money she had saved ran out, he returned to his abusive ways.
The story continues by saying that when the Spanish–American War began he volunteered for military service.
Hart then shocked observers by declaring that she hoped he would be killed by the Spanish.
A variation of this story has Bandman instead of her husband leaving Hart for war.
Hart was born Pearl Taylor in the Canadian village of Lindsay, Ontario. Her parents were both religious and affluent, those provided their daughter with the best available education. At the age of 16, she was enrolled in a boarding school where she became enamored with a young man, named Hart, who has been variously described as a rake, drunkard, and/or gambler. The two of them eloped, but Hart soon discovered that her new husband was abusive and left him to return to her mother.
Hart reconciled with and left her husband several times. During their time together they had two children, a boy and a girl, whom Hart sent to her mother who was then living in Ohio. In 1893, the couple attended the Chicago World's Fair, where he worked for a time as a midway barker. She in turn developed a fascination with the cowboy lifestyle while watching Buffalo Bill's Wild West Show. At the end of the Fair, Hart left her husband again on a train bound for Trinidad, Colorado, possibly in the company of a piano player named Dan Bandman.
Hart described this period of her life thus: "I was only twenty-two years old. I was good-looking, desperate, discouraged, and ready for anything that might come. I do not care to dwell on this period of my life. It is sufficient to say that I went from one city to another until some time later I arrived in Phoenix". During this time Hart worked as a cook and singer, possibly supplementing her income as a demimondaine (prostitute). There are also reports she developed a fondness for cigars, liquor, and morphine during this time.
A story of this period claims that while in Phoenix, Hart ran into her husband. He convinced her to come back to him and move to Tucson. Once the money she had saved ran out, he returned to his abusive ways. The story continues by saying that when the Spanish–American War began he volunteered for military service. Hart then shocked observers by declaring that she hoped he would be killed by the Spanish. A variation of this story has Bandman instead of her husband leaving Hart for war.
Pearl Hart