I just defeated NORG (so I'm toward the beginning of the second disk), and I've already noticed the little trend you described. Squall still seems pretty apathetic about most people*, but given that the cover artwork is Squall holding Rinoa, I know that he's going to eventually start feeling something, and I don't know how that's going to be believable.

BUT my enjoyment of FFVIII has been immensely bolstered by the recommendation made by a friend, that I keep in mind that everyone in your party is a teenager, and that their young age in reflected in their personal maturity. That's helped alot... and I think I'm going to go right now and write a blog post about this?

* His mancrush on Seifer being a notable exception, maybe?