I always like how people who learn English as a second language actually have better grammar than those of us who are native speakers.
Well if you take him around with you you can get more influence with him to open more dialogue, but that is only if you have not jedified him yet. This dialogue is a one time thing though - it's not like Handmaiden or Mira dialogue which kind of just sticks around.
If you have not already done so, I would look for an influence guide (there are tons of them). So, no this is not a bug
Welcome to Lucas Forums!