If we're talking strictly games, I first played Final Fantasy X when my brother brought it home one time. He was (and still is) a big fan of VII and VIII and I quite liked them as well so we were both psyched to see what this game would be all about. Turned out to be pretty fun. Though it took me years to come to appreciate it the way I do now; but here I am ^^

As for visual novels, I'd just gotten done reading through Higurashi no Naku Koro ni's main 8 episodes when I asked Ultima Shadow what he thought I should read next, and among my considerations were Umineko no Naku Koro ni and a couple others. I was 'subtly' nudged towards Umineko so I started it straight away. I somehow managed to finish it in two weeks with university on the side. And I say 'finish' loosely because in rushing through it like that I managed to miss several facts that are only ever hinted at and not stated outright. And I failed just about every single mystery. So, uh, can't recommend doing it that way. Again, like with FFX, it took me quite a bit of time before I ended up loving it as much as I do now, but it was still an amazing experience.