I like the feelings given here of nostalgia for whomever one used to be. I think they come through clearly. I think the emotion can't really shine through without some additional elements like music or a little more story structure or eventual moving forward. with a little choice for the player or some more events that occur that we can identify with, I think this could be improved but I do appreciate the style you went for.

There's some nice writing here! I'd love to have more of the "game" present though. At present this is just a short story that could just exist on paper. I think it'd shine if you used the medium of games to help express the feelings you wanted to express.