you two really put baby in a corner here, how exactly am I supposed to say anything fresh and half as brilliant than either of ya'll? i love your readings. they build on each other beautifully and their slight differences give us fascinating ways to approach the same scene.
i want to go back to @idwaitforthelion's stellar questions: "Is he afraid of the cost to himself? Why is the cost so big Jack? Is he tired of trying? Is he frustrated at Robby?". I want to float the possibility that there may indeed be some sense of, as you put it, cost here that's fueling his reluctance -- a sense, perhaps, that if Jack doesn't walk this line very carefully with Robby, he really could stand to lose something.
As Alethia says, Jack will often push Robby but no so far that he'll alienate him and, as Astronomical points out, this is likely far from the only time he's dealt with someone for whom suicidality has been an issue. I love the idea that Jack's reluctance when Dana prompts him to reach out to Robby is coming from a place of wanting to avoid an inevitable fight with him if he can help it (like Alethia, I also get the sense this has now become an exhausted sticking point between them -- consider, for instance, how badly the subject of therapy lands between them in the s2 finale versus the s1 finale). I also love the idea that Jack might have also let himself believe Robby hadn't gotten "that bad" under his watch (as Astronomical's reading highlights so beautifully). To his credit, Robby does put up a front to suggest he's jumping through the therapeutic hoops: he tells Caleb, for instance, that he's seen two different therapists already (even if he's almost certainly not giving them a real shot) and I'd be shocked if he hasn't told Jack much the same.
So, what does Jack really stand to lose if he pushes harder, forces the conversation, gets into yet another fight with Robby about therapy and they finally broach the topic of Robby's suicidality? I think the singular nature of their relationship tells us something: yes, of course, Jack is his emergency contact (wow!!). But it's telling that, when all else fails, Dana goes to Jack specifically -- not Noelle, not his favorites amongst the residents, and she certainly doesn't pick up the phone and try to call Heather, Janey, or Jake (that'd be nuts for all parties involved, our girl is too savvy for that). In my reading, the text of the show (and Shawn and Noah's performances) really speak to a long history between them, a singular trust and ease and capacity for vulnerability that they don't demonstrate elsewhere with anyone else. What does it mean to be the only person Robby trusts like that? What does it mean that Robby seemingly lets nobody else in that close (and still holds Jack at a considerable emotional distance all the same)? If Jack were somehow to push their relationship past a breaking point (by, say, forcing a conversation that he knows will likely end in a nasty fight and, btw, canonically it does!), who else could possibly get through to Robby in his stead? Who else would Robby speak to or trust in that way? This is a slightly different can of worms, but Robby's season-long tension with Langdon is proof, I think, that once his trust is lost, it is incredibly difficult to earn back. Why is the cost of speaking so big for Jack? Perhaps because there's some sense that, if he challenges Robby to the point of alienation (at a time where people genuinely think he's going to take his own life, no less!), he stands to lose him entirely in more ways than one. And yet he makes the choice to speak anyway (and, in my reading, to potentially risk the goodwill between them) and the gamble pays off in one of the biggest scenes between them in the series thus far!
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