Shawn knew if something happens to Aarvi, Aaron wasn't going to listen to anybody. He won't be surprised if Aaron leaves the country or stops seeing anybody. So he asked so that they could find a solution to the problem that might possibly occur.
Thinking of Aarvi, he wished for the family and the family love that she finally got to stay with her. He didn't want her to think his grandfather was pitying her or making up for the past.
Leaving it apart, he wanted to convince Jordan to speak before Aaron loses his cool. Aaron had already waited for three whole years for Jordan to speak voluntarily. His patience was running out.
Jordan was holding his cane avoiding looking at anybody. He had daily persuaded himself to speak about it with Aaron, if not Aarvi. Even though he didn't do anything on purpose, he was still responsible for his actions that affected Aarvi.
This won't be a large arc. Only a few important events like first, last plus a crucial.
Much Love,
Munchkin