One of my first interactions with The Stranger was through its classified ads. I was 22 years old and, searching for a date, I responded to a personal ad placed by a young man who claimed to be "in publishing." That sounded promising. I imagined a smoldering bookish waif, scarf wrapped around his neck, stylish glasses just so. I wondered where he might be employed in this city of no major publishing houses, but I didn't let the wonder linger long enough to pull me out of my fantasy. I was certain I would soon be meeting a member of that almost nonexistent Seattle species: the young, gay editorial assistant. It was a thrilling idea.

We met at a bookish coffee shop on Capitol Hill. He was already there when I walked in, and I identified him by his expectant look—not, sadly, by his closeness to my fantasy. There was no scarf. There were no glasses. "Waif" was not the right word. And worse, he was only in publishing in the sense that a young man who creates informational brochures for the city's water department is in publishing. That's what my date published: water pamphlets.

Ah, well. Desire—it makes dopes of us all. I became one date wiser, and somewhere in the accounting department of The Stranger a counter ticked off one more classified ad sold. It was, I realize now, all part of an exchange as old as the modern newspaper, and really as old as cities: the attempt to match desire with its proper object in a chaotic urban environment where everything seems easily at hand, but, paradoxically, the right thing is so hard to find.

In Strange Red Cow, a fascinating new book of classified ads from the past, researcher Sara Bader provides a history of this unrelenting search by desire for its proper object—via newsprint. (The title refers to a farmer's search, publicized in a classified ad in 1776, for the owner of a "strange red cow" that had wandered onto his property.)

The idea of the classified ad goes at least as far back as the ancient Roman city of Pompeii, whose ruins, Bader notes, still feature walls adorned with scrawls announcing houses for rent. But she focuses primarily on the printed classified ad as we now know it, and its evolution from afterthought (the first English-language newspaper declared such advertisements "not properly in the business of a paper of intelligence") to an essential component of civilized life (not to mention newspaper revenues).

It is remarkable to find in this compact, well-designed book both an ad placed in 1769 by a frustrated Thomas Jefferson searching for his "knavish" runaway slave Sandy, and an ad placed in The Stranger in 2004 by a shy woman seeking another shot at a man who one night wore an "I Love Nerds" shirt to a Bollywood party at the Mirabeau Room.

It is at once alarming and comforting to learn that certain desires (especially those of tentative, shy people) recur regardless of the era. This ad, from an 1861 edition of the New York Herald, should sound familiar: "On Wednesday afternoon a lady with a black, silk, quilted hat walked nearly side by side with a gentleman in a drab overcoat from Tenth to Fourteenth Street, in Broadway. Both were annoyed by the wind and dust. Her smile has haunted him ever since. Will she send her address to Carl, Union Square Post Office?"

The one thing that Bader's book does not discuss, disappointingly, is the question currently on the minds of everyone in the newspaper industry regarding classified ads: What happens to newspapers as the gratification of desire increasingly becomes something more easily done over the internet than in print? What happens when the printed classified ad is a thing of the past? The ads reprinted in this book, and the urgency with which they were originally placed, suggest an answer: Desire will always seek the easiest path to satisfaction, and if newspapers want to remain a place where desire and offering (lucratively) meet, they will have to go where the desire is now: online.