Wait, it's not repeatable? It might even be worth submitting this as a bug.
The repeatable question in Gale's case is instead checking in on his mental health.
I'm greedy. I want them both. :P
Be greedy! ^^ To be honest, I never felt this question was necessary for Gale though because the importance, the relationship holds for him, is illustrated through so many small details in the regular dialogue.
