The painting depicts an office occupied by a young woman in a short-sleeved blue dress who is standing at an open file cabinet, and a slightly older man who is perhaps in early middle age.

"[1] So this is not a prestige office — a fact that is reinforced by the awkward lozenge shape of the room and by the small size of the man's desk.

Second, the wind has blown the dress tightly around her legs, revealing her voluptuous figure to the strangers on the train — but not to the man who stares intently at another document.

By contrast, listless curtains in other Hopper paintings like Eleven A.M. (1926)[4] and Hotel by a Railroad (1952)[5] seem to imply emotional stagnation or an inability to connect.

Apart from the relationship between the two figures, the suspenseful mood arises from the circumstance that they are apparently poring over confidential material at this late hour, looking for a certain document that has yet to turn up.

"[6] The man's intense concentration suggests that the matter is critical to him—he has not bothered to take off his jacket despite the fact that it is warm enough for all the windows to be open, and he seems not to have noticed the wind which has caused a page to fall to the floor.

On the back wall Hopper has painted a section of artificial light, which in turn dramatizes the point where the man and woman will interact with each other.

Early proposed titles for the painting included Room 1005 and Confidentially Yours,[9] reinforcing the idea that there is a deeper connection between the man and the woman, or that they are working jointly on a matter that involves a high degree of trust between them.

As in other nighttime scenes, Hopper had to realistically recreate the complexity of a room lit by multiple, overlapping sources of varying brightness.

During this time, according to entries in the diary kept by his wife Josephine ('Jo'), he occupied himself by reading a book by the French poet and essayist, Paul Valéry.

Jo's diary records that their attention was drawn, in particular, to Botticelli's 15th century The Birth of Venus, which she had seen before their marriage at its home in the Uffizi.

Jo's diary for this date notes that "he has a black and white drawing of a man at a desk in an office & a girl to left side of room & an effect of lighting.

"[11] By February 19 the canvas had progressed to the point that Jo observed, "Each day I don't see how E. can add another stroke"—but also that his changes were making "this picture…more palpable—not fussy ... reduced to essentials ... so realized.

Starting shortly after their marriage in 1924, Edward and Jo kept a journal in which he would, using a pencil, make a sketch-drawing of each of his paintings, along with a precise description of certain technical details.

[12] The journal contains a scratched-out note stating that the painting was sold in spring 1948 to the Butler Art Institute in Youngstown, Ohio for "1,500 -1/3", paid on July 27, 1949.

Another note, immediately below, contradicts this, stating that the painting was sold to the Walker Art Center in Minneapolis for the same amount, on June 27, 1949.