First play (2003)
I remember I wasn't supposed to play it until I'd finished something school-related (done an exam, some homework, a project, something that wouldn't be for at least a few days), but I snuck out of my room in the night and played it in the little landing outside mine and Matthew's rooms (downstairs at Pine Lodge).
Still one of the best games I've ever played. The mood, aesthetics, characters, story, execution, experience, music, gameplay, rain, it's all beautifully put together.
Second play (5th - 26th November 2013)
Wii U (HD version)
Played through it again after I got the Zelda edition Wii U which came with its HD remake. I guess I went for as close to 100% as I could, quickly, and ended up collecting most if not all of the items and heart pieces (I imagine I missed a few) as well as taking pictures of every enemy for the figurines (once I'd figured out how to get the colour camera).
Obviously the story is no longer as compelling to me, since I'm a) older and more experienced, and b) pretty familiar with it by now, but it was fun to play through it again, enjoying the HD graphics and Wii U controls. I'm watching the end credits now and the music is so awesome :P