Back in the early 90’s, I saw an article about the Straight Dope in the Wall Street Journal.
Girlfriend in college gave me one of the books. That would be about 1991. This was at the University of Illinois and she was from Chicago.
The TV show, which led me to the AOL site, and from there the board, and the books. You’ve all been stuck with me, ever since.
JKellyMap—Heh! And I first found the Wallace/Wallechinsky’s Book of Lists at the “Book Exchange” at Hamilton Air Force Base, in the early 90s. I seem to also recall finding a copy of the hobbyist’s guide to programming an Altair, too. 
I found the first straight dope book while browsing in a Coles bookstore in the 80’s. I loved the book and the irreverent answers. It was one of the most re-read books I had. I was thrilled when over time I saw book two and three come out. I eventually found this website and have been here ever since, even though I do not post much. I honestly thought Cecil was real.
Mocker.
I would go to the book store all the time and I would often browse the reference section because I liked question and answer type trivia books (Imponderables, Why Things Are etc.). On one of those trips while in high School I discovered the first Straight Dope Paperback (the black cover one). I loved it and bought every new one as they came out. Never read the column in a newspaper, only the books and later on line.
That led me, in College in the early 90s to find Alt.fan.Cecil-Adams where I became an active poster and that then led me to here.
When I ran into Cecil at a party thrown by Sam Wagstaff around 1977 and we both pondered that we were probably the only two straight guys there, he mentioned his column to me as a passing thing. He wasn’t sure if he was going to keep doing it. I encouraged him to keep at it, who knew that ignorance was so prevalent.
Chicago Reader c. 1991
My friend commuted into the city for school and would grab a couple copies to bring back to suburbia. So I’d get my copy from him. Went back and bought the books from a second hand store.
I was watching a show on TV about the guillotine and they mentioned that one guy blinked some number of times after his head was chopped off. I was a bit skeptical so I searched for it on the internet and found Cecil’s article on beheading. There were more columns on the site of course, so I went digging and I was hooked immediately. The web site was advertising one of the books at the time, which is how I found out about the books. It took me a while to warm up to the message board. I didn’t join that until maybe a year after I first found the site. I read the columns regularly (still do) and I eventually ended up purchasing all of the books.
I started reading the column in the Chicago Reader in 1994, when I attended the Illinois Institute of Technology.
Are you sure that wasn’t Albuquoique?
Shoulda made a left at Abluquerque, you mean? 
Had a roommate in the 90’s who had a couple of the books. Sometime after 2000, I found the Straight Dope online and in 2004 joined the SDMB.
Found a book in the late 90s, then later saw it linked somewhere I can no longer recall. Once I found the online articles I followed them for a couple years before signing up and joining in.
My worn copy of The Straight Dope was in its ninth printing: Feb 1989. I’m guessing that I first came across Cecil in a local freesheet, maybe in mid-1988. I read a lot by the urban folklorist Brunvand at the time. I was hooked. Before the internet you used to have to dig for this sort of stuff.
I emailed Cecil a couple of lame questions before I finally signed up here. I confess I’ve been somewhat shaped by the underlying rationalistic standards and ideals of Cecil and this message board.
When I was reading the book, I realized that a friend had referred to Cecil’s column in the Chicago Reader at least once: this was probably in 1983 or whereabouts. Discussions of decapitation tend to be memorable.
Long, long ago, the line in the college bookstore was horrendously long and slow. It wound through aisles of lighter fare just before the cash registers. One of the Straight Dope books looked interesting, so I browsed through it while I was stuck near that shelf. The only question I remember was the one about the calorie content of cum.
Many years later, while reading Neil Gaiman’s blog, somebody asked a question and Neil said he didn’t know the answer and referred them to The Straight Dope message board. I only halfway remembered the title of that book and had to do a search to see if the board was related. It was. For awhile I only read the articles, but I got to the boards eventually.
From maybe 1999 to 2003ish I used to read the Apolyton Off Topic Forum for my current events/politics/culture discussion, and was occasionally linked to the SDMB. Eventually I guess I just never clicked the Back button.
Apolyton is a Civ gaming site (as if I need to explain that to the SDMB!). Haven’t been back there in ages, and it still feels about the same.
The short-lived Southwire carried both “The Straight Dope” and “Life in Hell”. The other alternative newspaper in Atlanta did not. Ironically, that other paper was Creative Loafing. (This was about 1985 or so). The column led me to the books (some of which had me literally snorting aloud with laughter in the middle of Oxford Books), and then in about 2003 or so, I joined the SDMB. Frankly, I only occasionally read the Master’s columns anymore; but I check the SDMB about every day.
Like many on this thread, I browsed a SD collection at a bookstore, bought it, and later all the other volumes.
I found the website through AOL - sometime maybe early 1997? I then worked my way through all the archived columns - back when that was available. Once I’d read everything I could find, with some trepidation I ventured over to the boards. It didn’t take long until I was hooked on those as well. I lurked until after P2P and signed up as soon as it was free again.