It sounds like you've hit some sort of glitch Ricc. I'm having the same problem too only because I merely did not happen take the right NPCs with me at the key times I needed them around to gain influence. And on Nar Shadda, there are several places where you can gain influence w/ multiple characters, and if you have two in your party that should react, only one of them will. I later found out that I lost many opportunities to gain influence w/ Atton just because the other NPC I was with spoke up first.
I really enjoyed talking to the NPCs in KOTOR1 so I was disappointed to find out, after 30 hours of playing (I tried not to look for spoilers too soon), that I missed a lot of dialogue just because I chose my NPC combinations poorly. I feel like my game is not at its full potential...! *sigh*
Is it really worth playing through again to hear more of the NPC dialogue? (spoiler:
?)