Yeah, I think that's what the problem was. I rested in a lot of different places throughout ToB and I never got that love talk to trigger except in the Pocket Plane. From there, everything went smoothly. I even went back to my save near the end of ToB and rested in the Pocket Plane and the romance finally triggered there as well. Hopefully most people don't have this problem since I just so happened to not rest there my whole playthrough.