My first time seeing the system in person was when I was 15 back in 99 with my father we were in a Sears at our local mall and I saw it running in all it's glory. It was in a slightly different style kiosk than the normal NTSC-U ones but really cool. I remember seeing Craazy Taxi running on it and the cool VMU's.
I also got the September 1999 issue of EGM, known as The Dreamcast Issue, and it really went over the console in fine detail.
After that issue I knew I had too have one. So I got my first job at 16 the following year of 2000 and it became my very first console I bought with my own money. I got 4X4 Evo and Shenmue, and bought an OZ of weed and had a 3 day spree off from work as I was a part time worker. I played Shenmue for 3 whole days straight not coming out of my room except for when nature called, I was hungry or I had to go smoke. I was super immersed into the game and it had my attention like no other game ever before or since. It was that game that showed me that games were no longer a kids toy but an art form equal to literature, theater and movies and music.
After the DC was discontinued, I will admit I sold it off after the games weren't stocked anymore at GameStop. In those times GameStop was the only place for used games, and once they stopped selling them it was impossible to find the games. I also didn't have the internet back then to know you could do all this amazing stuff with the system with no moods at all.
Around 2008 I discovered DCISOZONE and NullDC. I began getting nostalgic all over again for that High School sweetheart, so I started researching all the homebrew things it could do. My mind was utterly blown and I was super depressed I had not known this sooner. All the early years would have been so much more fun with it if I had kept mine and discovered homebrew.
In 2009 I registered to DCISOZONE, and purchased another console and the rest is pretty much history. I discovered this place that same year and been hooked every since. Now I have a modded Dreamcast with a GDEMU and 128gb SD card, a 20% overclock to 240mhz and 2 OC'd VMU's, a PS4 thumbstick mood and I was fortunate enough to get a DreamPi this year as well.