Or any Q&A columnist, for that matter? Where do they get the questions to answer for their first few columns? Poll random passers-by on the street? Have their brothers-in-law pose as Little Old Lady in Peoria?
Just for reference, here is the first column. On an interesting note (to me, anyway), the very first question came from the same neighborhood where I grew up - Rogers Park.
I don’t know the answer to the question, though. Sorry.
Thanks. All from the Chicago area, it seems. Maybe I wasn’t too far off with my guesses.
No more Holland LPs? pout
Well, keep in mind that The Straight Dope was (and still is) published by the Chicago Reader, a Chicago-based weekly, so it would make sense that the original questions were all from Chicago. Later, of course, the column was syndicated and later still moved to the Web, making Cecil the international authority figure he is today…
Yeah, but where’d the first questions come from? You didn’t see some journalistic-looking fellow chasing people down the street a few decades ago in Rogers Park, did you?
Maybe Cecil himself will stop by and answer this one. Haven’t seen him around here in a while.
Hey Cecil! You still with us, bud?
I wrote to a national Q&A column in a Dutch national magazine twice. Both times with an etiquette question. (For the Cloggies out there: Beatrijs Ritsema’s column: “Beste Beatrijs” in newspaper *Trouw * and weekly magazine HP/De Tijd.)
Both times, my question appeared in print, and only the slightest bit edited for style. So yes, I can personally vouch at least those two letters were real. 
The Skeptical Inquirer, official publication of CSICOP recently initiated a new column called The Skeptical Inquiree which solicits reader questions. The first question and answer was a topic of very broad interest which came from their staff. The final portion of that column (and always a sidebar to the subsequent columns) is a call for reader queries.
I dunno how the Straight Dope got their first few questions, but it seems a reasonably logical and straightforward practice to me that an annoucement about a new feature would be placed in the several issues leading up to the kick-off of the new feature requesting reader submissions.
Cecil was an ardent Jeopardy fan at the time of his first collumn. After he wrote it he asked Art Fleming to come up with the correct question.
Based on actual experience as a regular question answerer on a local level, at least, it’s often necessary to make up questions in order to fill the required space. People just don’t take the time or effort to actually write in questions as much as we’d like them to. I’m sure readers in a city the size of Chicago and certainly a national readership will generate more questions, but smaller publications either don’t have their own question and answer columns or rely on questions they write themselves from time to time.
Interesting. So they could have been made up, or the Chicago Reader could have posted an announcement asking for questions in the couple of months leading up to first column, or Cecil could have accosted people on the street and demanded that they ask him something.
Beats my speculation that he just drove around Chicago with the bumper sticker “Ask me about my merkin!”
Good question, Sentence!
Nothing to contribute, but I think it rules that you mentioned Peoria in the OP.