Well, now that people are actually reading this thing, I guess I should mention how I got here.
1981-1985: Born in Waukegan. Don't remember much, but the photographic evidence indicates that I enjoyed riding my tricycle.
1986-1996: Childhood in Winthrop Harbor/Zion. First bike without training wheels was a pink and purple Huffy Heartthrob (seriously), first "grownup" bike was a Murray mountain-style thing. Rode around what passed for my neighborhood between the park, the video store, the softball diamond, and an awful local dive called Frank Bank that doesn't exist anymore. During the summer the whole family frequently took excursions up "the bike path" to Pleasant Prairie or down to Illinois Beach State Park, occasionally crammed all the bikes into the minivan and drove to Van Patton Woods to ride the Des Plains River Trail.
1997-2000: High school at IMSA in Aurora. Brought my Murray to campus, but only rode it maybe once or twice a school year because back then I actually preferred inline skating for fun and locomotion.* Listened in awe to friends' tales of biking all the way to Elgin or DeKalb and back. Summers brought the Murray back home and rode between Kenosha and Waukegan every day out of sheer boredom and lack of anywhere good to skate. Graduated and got a job answering phones at North Point Marina for the summer, was a "bicycle commuter" because it was too close to drive but too far to walk.
2001-2004: College at the University of Chicago. New bike, a used Jazz mountain bike that I bought at Zion Cyclery with my last paycheck from the marina and named Christopher because I'd just seen "Christine" and thought a bike that attacked people who tried to mess with it might be useful on the south side of Chicago. Rode on sidewalks, went the wrong way down one-way streets, blew through stop signs at top speed, and committed various other infractions because I didn't know any better. Rode from campus to my job, to campus from my dorm, around Promontory Point, up and down the Lakefront Trail. Rode the entire Lakefront Trail from end to end to end one memorable day in June of '03 and claimed a victory.
2005-2008: First job out of college at the University of Chicago Press. Bought a brand-new hybrid from the local cranky guy because his was the only shop selling them and I wanted something faster that I could still ride like a mountain bike. Named it Avenger: (1) I was watching a lot of Adult Swim, (2) the CTA had just announced a doomsday budget and I meant to avenge the loss of the #6 Jackson Park Express by never taking CTA again (hahahahaha!), (3) it's heavy enough to leave a pretty good dent. Finally learned about and joined the Chicagoland Bicycle Federation. Became a Bike Person when I realized that I used to bike because I don't have a car, but now I don't have a car because I bike instead. Dove headfirst into the culture built around the thing I'd been doing my whole life thus far without really thinking about it. Began to explore the City of Chicago beyond my insular little neighborhood, parts beyond the city when Metra finally allowed bikes on trains. Went on the GITAP in '06 to prove that I could, went again in '07 and '08 because I had so much fun, continue to dabble in touring mainly because I want to go places but don't drive anymore. Purchased a folding Breezer so I could boldly go where I had not gone before (e.g., Milwaukee); named it Scooty-Puff after an obscure Futurama reference that no one ever gets. Now I can multimode!
2009+: Your guess is as good as mine.
*In case you're wondering, I stopped skating a week after college graduation when I fell on my butt and broke my tailbone and then found out the hard way that I technically didn't have health insurance. I keep meaning to give it another try.