I first saw Escaflowne (and soon after, Trigun) and really got into anime around 1999 or so, and my first con was Otakon 2004, so about 5 years. That is, unless you count stuff like Littl' Bits when I was 5, before I knew what Japan was, let alone that a cartoon was made here or there or anything. In that case it was about 14 years.
I've been watching stuff like Pokemon and Yu-gi-oh since I was like in 4th or 5th grade. I actually DID know that they were from Japan by the time I was in about 6-7th grade. Then I started watching stuff on Adult Swim...then I went to my first con at the end of my 9th grade year.
I started about 18 years ago with Tonari no Totoro (well, before with dragon ball, candy, sailor moon, etc.) but Totoro made me look for more stuff like it, fortunately the video rental place had some Miyazaki and Tezuka, as well as some Heidi action. And consolidated at the age of 13/14 when I started working at a "Internet cafe" as a clerk about 11 years ago.
As for conventions... I've never been to a real one, went as a photographer for a small one though, about 3 year ago.
The first time I watched anime (and knew it was anime) I was 17 and my ex-boyfriend showed me Record of Lodoss War: Chronicles of the Heroic Knight. That was also the first year I ever played role playing games and larped. After that a friend showed me Trigun and that was that - I was an anime fan. I am now 24, so that was 7 years ago. It is a shame that there haven't been any shows the past couple of years that really caught my interest. My first con was Otakon '01 or '02 (I don't remember), but I spent most of the con helping my then-boyfriend-now husband sell his artwork and merchandise. I have to say, I only really enjoy cons if I am doing something at them. I doubt I will ever go to a con again without selling, presenting, hosting, etc.
I'm not really much of a CON goer. Every CON I have been to was either as a guest of the CON or a guest of an exhibitor at the CON. I don't think I've ever paid for a CON badge or anything other than food and toys at a CON.
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Then I started watching stuff on Adult Swim...then I went to my first con at the end of my 9th grade year.
So roughly.....4ish years, I guess.
First anime convention was Anime Next 2006.
As for conventions... I've never been to a real one, went as a photographer for a small one though, about 3 year ago.