...Well, I hope he manages to succeed. It sounds like something like that has the chance to break him down, if he stays there too long. That wouldn't be good for him at all...

[...she says it like she knows something about it, but...if anything, her look goes a bit softer.]

You must be doing something about it too, then, right? He must be very proud to have a friend like you on his side, helping to support his goals...