I bike in urban Seattle. I got my first road bike, a 65cm, unidentified make (it was painted when I bought it--people guess all kinds of things: "European," English, Schwinn... I don't know, but the only parts on the bike that might be original are the shifters, which are vintage SunTour...) steel touring bike with 700x28 wheels and 18 (now 24) speeds. I started riding from the dorms to the opposite side of campus two years ago. I moved off campus and started biking the less than one mile to campus, in any weather except icy roads, and even then sometimes. I decided to do Seattle to Portland last summer and started riding around Lake Washington for practice; did STP in one extremely long day (16:49) and have been hooked since. I don't go on recreational distance rides nearly often enough, but love it every time I do.
Now I work as a "messenger," ie. I deliver sandwiches in a ~20 block radius. I get paid to ride my bike, and I love it. I ride pretty rudely while I'm working, but I'm always paying more attention than anyone else on the road and have yet to have a collision or even a particularly close encounter while working. I generally don't respect traffic signals, but heavily respect several thousand pounds of steel. The main thoroughfare on which I ride has pretty slow traffic (20mph when there's no traffic) and heavy bus traffic, so if there's no oncoming traffic and everyone is stopped behind a bus, I'll jump into the wrong lane and be 3 blocks away by the time the bus moves. I'll run red lights, but only if I know I'll be out of the intersection for at least ten seconds by the time the next car comes.
I'm very familiar with the streets I act like a jerk on, so I know how cars move around here, I know the hidden corners and driveways, I know how long it takes a car cresting the hill to get to intersection x, and I know how the drunk frat boys get home when the bars close. I've never been fleet of foot, so it's pretty exhilarating being nimble on these streets.
I always wear my helmet and always wear front and rear lights at night, and typically wear a bright red and black jersey for work.
I also now ride a single speed Schwinn that I plan on re-converting to a fixed gear when I have the money to get a flip-flop hub and the time to build up a wheel for it. For the time being it's just a cruiser bike, but before I stripped some threads off the hub it was a fixie that I rode a bit for work. I don't ride it much as a single speed so I'm eager to get that fixie wheel built.