When i was about 5? a small beautiful sparkly royal blue thing with a royal blue banana seat. passed onto my brother.

age 8-11: a slightly bigger girls raleigh.
around 11, my first ten speed: a Fuji, w/24 inch wheels. Still in my parents' garage, keep meaning to donate it to the bike kitchen

then, at 13, i took up with a mid-'70's Motobecane Mixte Grand Jubile 12 speed. Still riding that--i love it. It's got a pretty good gear range, and suntour bar end shifters and suntour cyclone deraileurs. Still going! I have taken it touring, and used it as a city commuter (with hills!) for about 7 years.

In college i rode a pink huffy ten speed, and i had a cruiser for a while that i think got stolen one summer. or maybe that's how i acquired the huffy. Bikes were a bit less loved in college. people traded them, and i just used them to get around campus, rather than taking them on rides.

also currently in the stable are 2 bikes i built up from frame and fork:
an older Bianchi Eros reparte corso frame, probably from the early 1990s, with mainly ultegra and 105 components.

and an old orange Le Jeune Tour de France 10 speed, built up for more relaxed road riding (upright bars, bar end shifters, and the rest all crappy old french components--but they still work!) which is just so cute.

Of the three i have now (motobecane, bianchi, LeJeune) i'm not sure i could part with any of them. And, i'm too cheep to get something fancier. Though i wish the surly long haul trucker came in my size with 700cc wheels, rather than the smaller ones...