[What you need to know to start the day: Get New York Today in your inbox.]

The second time I met the man I would eventually marry, we sat down to Thai food in Brooklyn, and he asked me what my favorite building was in New York. Relatively new to the city, he posed the question as a litmus test, it seemed, to see who would answer honestly and who would strain to offer a contrarian response. Without any hesitation, I said that I loved the Chrysler Building beyond any other, and he laughed appreciatively at my total lack of interest in saying something original.

The Chrysler Building is beautiful, but that alone does not explain the unequivocal, emotional reaction it provokes. Like all skyscrapers of the Modernist period, it conveys the grand ambitions of a new machinist age. But it also suggests something more intimate, that aspirations do not always play out predictably — that how you imagine you will experience the pinnacle is not, in fact, how you might actually experience the pinnacle. Distinctively, the building literalizes this view, forcing us to look up — delivering circularity rather than conclusion, surprise over certitude. Designed in the 1920s and completed in 1930, the spire was assembled the day before the stock market crashed in 1929.

The Chrysler Building, currently owned by an Abu Dhabi wealth fund and the Tishman Speyer real estate empire, is now going up for sale. There is not an obvious buyer. Despite its significance, it is plagued by the same problems that face so many office buildings in the city that went up between the 1920s and the 1970s, many of them, like the Chrysler Building, on the east side of Midtown. They lack the light and efficiency of contemporary working spaces, and they are hugely expensive and time-consuming to repair and modernize, with warrens of rooms, interior columns and low ceilings.