This a long one :))
If you don't get it, TC was projecting himself in the dialogue.
"or maybe he wasn't (happy)"
"Maybe he doesn't want to leave here ever"
In the AU, TC hated their brothers (Archivists) so they left and Wittebros found him! I basically parallelled their story with Caleb's, how they both hated where they came from and found happiness in the BI
Wow so now Pip feels conflict!!! :D