I have almost the same story. I was also a freshman in High School, and my first concert was seeing phish the next night on 11/19/95. I started to listen to Phish with my cousin who was two years older around the summer of 1993. As soon as I heard Junta, I was hooked. I remember loving the lack of structure and the jams that Phish was able to produce. I had been listening to the dead for a couple of years with my older brother, but I remember thinking the dead were amazing, but phish was for my generation.
On the day of the concert, my friends parents dropped us off, who were total deadheads and instructed us to stay away from the nitrous tanks. My friend and his brother were named after grateful dead songs, so his parents definitely knew what we were about to face in the parking lot. There were three of us in the car each with about a quarter of the brown frown. We were 14 so it did the job.
Anyways, I was blown away from the whole experience, and I remember thinking 2001 was the best song in the world. The parking lot scene was so inviting, and even though we must have been the youngest people there, I don't remember feeling that intimidated. I knew afterwords that I was going to be seeing this band for along time, and that I had finally found the music scene that would change the rest of my life. The lot in 95 was so good, and was not sketch at all in Charlotte. I was heavily into skateboarding and enjoyed art, and noticed that there were others in the lot who were into the same things. Also trading tapes back in the 90's was great. I met so many people who were just as interested in phish and trying to get a copy of a first gen tape. With the internet and torrent sites, it seems like people just getting into the scene miss out on this aspect. Maybe technology has allowed people to get more music, which is a good thing.
I continued collecting tapes (XL11s) or MP3s, and seeing phish at least one show for the rest of their tours. I used to try to get the tapes as soon as they were available to hear how the new songs were played live, and the new musical style. Phish crossed so many musical boundaries playing funk, jazz, rock, etc. I am so happy that they are reuniting, and hope that they will come back with more energy than the last time around. Although Greensboro 2003 has to be one of the best phish shows that I have ever seen.
I can't wait to see what phish will do in 2009.