[3] The newspapers covered his petty crimes associated with life on the margins of society such as burglary, disorderly conduct, disturbing the peace, and vagrancy.

[14][8] Jennie Pickerell shared that Allen was allowed to wear boys' clothing and indulge his interest in masculine activities from a young age.

[4][14][15] Allen worked many kinds of jobs, such as waiter, hotel clerk, bartender, bouncer, shiphand, and cowhand.

The Seattle Star reported that Quappe had not known that Allen was transgender until he was arrested on suspicion of theft, having stolen an overcoat at a dance in Ballard.

[27] According to The Victoria Daily Times, part of Quappe's infatuation with Allen was that he bore a resemblance to a man to whom she had previously been engaged, who had left her to marry another woman.

[27] After her death, Allen insisted that Quappe was aware of his transition, but police did not take him at his word because in all their letters she called him Harry Livingston.

[30] According to a profile published by The Seattle Star in 1915, Walters' manner of death was to throw herself from a 'cliff' at Madrona Park because she discovered he "was a woman".

"[31] The third of Allen's lovers to die by suicide was Pearl Waldron, who shot herself in the chest with a 32-caliber revolver in Denny Park on November 4, 1903.

[17] While incarcerated, the chief of the Spokane police tried to force Allen to switch to wearing skirts and feminine undergarments.

The press and public were interested enough in what type of clothing he wore that they ran at least five articles during his two month stay at the county jail on whether Allen had donned a skirt yet.