Because her readers did not know who she was, Long often jested in her columns about being a "short squat maiden of forty" or a "kindly, old, bearded gentleman."

In college, she began growing herself a modest reputation as a journalist, writing a review of "Vassar Dramatics" to the Poughkeepsie Courier in June of her senior year as well as participating as an editor in 1922's Vassarian.

Even with that target audience, it (like most new publications) struggled financially in its early days; by May 1925, the astute Ross—looking for ways to increase readership—realized that Long was just the sort of writer who would.

Her witty, satirical column was called "When Nights are Bold," the title of which changed to "Tables for Two" with the issue for September 12, 1925 and ran until June 6, 1931.

[4] As the archetypal flapper, Long's columns offered women a glimpse of a glamorous lifestyle where they could enjoy many of the same freedoms and vices as men.

Zeitz notes that Long's cubicle was originally on the other side of the building from her assistant, and after growing tired of running back and forth to exchange information, they made the trip on roller skates.

[6] Throughout her career, Long's work appeared in numerous formats, and in 1928, she was recruited by the editor and screenwriter, Gene Fowler, to contribute, along with Ben Hecht, Ring Lardner, Westbrook Pegler, and Walter Winchell, to The New York Morning Telegraph, and in 1936 Long was, for a short time, under contract to Paramount Pictures.