He's spoken openly to you, and that matters. In a situation like this, too much pushing can make him feel even more inadequate. Let him breathe. After a while, if it becomes apparent that he's not going to make it, I would let him go. But right now, enjoy his company. See how it goes. The job loss, the lower income, and the pressure he feels are real, but they do not automatically mean he is pulling away for the wrong reasons.