Perhaps you've heard of the OS-tans. Basically they're cute/attractive female "moe" ("mo-eh", not "mo") anthromorphizations of operating systems. For example, 95-tan is a very composed traditional-looking japanese woman with a kimono and a katana (the katana apparently symbolizes how 95 finally made microsoft dominated the PC os field) unfamiliar with things like USB ports; XP is a young girl in flashy clothing and an insatiable hunger (reflecting XP's apparent memory-gobbling ways).
According to the
wiki entry on them, the whole idea spun out of Futaba Channel, a forum frequented by Japanese Otaku.
But, yeah, that's all beside the point, I've come bearing a pic of the "-tan" version of Portal's GLaDOS, aka GLaDOS-tan:
http://i26.tinypic.com/v7hbnq.jpg
Ok, so it's highly unlikely that GLaDOS could be considered cute (more of a psycho girlfriend, methinks); but if, say, the orange sphere (the one that's like a kid, remember?) suddenly became the dominant personality for GLaDOS, it could happen, I think.