I also totally missed this thread. I found Head-Fi at age thirteen while seeking an upgrade to a set of Sennheiser PXC-300s (I think). Someone recommended I try Grado's, so I bought a pair of SR-60s from TTVJ sometime in early eight grade. Truth be told, I didn't like them: the midrange seemed harsh and unbalanced; the treble piercing. I desperately wanted RS-1s, though, for all the wrong reasons.
On my fourteenth birthday, my dad drove me to a meet in NYC, where I heard Grado's finest and a bunch of other high end headphones for the first time. I was instantly captivated an astounded; I couldn't believe that my SR-60s and this particular pair of RS-1s were made by the same company. Needless to say, I left that meet with a passion and a purchase list.
With a part time job and some diligence, I bought a set of RS-1s and flats from TTVJ around the end of eight grade; and a few months after that, an EAR+ HD. Some sort of high end source was next on my "to-do list," but then I discovered my passion for photography, which ate money faster than I anticipated.
I'm now sixteen, and with my camera setup virtually complete I'm considering a return to a more serious side of this audio hobby. I guess we'll see what junior year has in store for me.