It was winter and suddenly his screen was a fuzzy grey, with funny looking windows, instead of the comforting (to me) windows teal.
At the time, it represented to me, a change into the unkonwn. As it was (assume) the start of a new contract (my dad worked at home alot) it was also a time of financial pressure.
So to me, I hated X, and how it looked. It was to me, the equivalent of a brutalist housing block. Well built sure, but foreboding to look at.
Later when I was I was using Linux my self (around redhat 5/6) If you suddenly saw that you were dropping into a "natural" X, It was a sign that you'd fucked up the window manager, or that the switch between gnome and E (or which ever one you were trying) had gone wrong.
I kinda like it now though.