So what is your suggestion if we notice he has had a bad day? How can we approach the "I care how you are doing" without appearing needy and pursuing?
See my AOSs example, above. Or, simply do nothing.
It's not your job to perpetually make him feel good about himself. That's co-dependency. It's also not your job to shelter him from the consequences (a heavy heart, a lot on his mind, etc.) of his recent decisions regarding your marraige. It is GOOD, and HEALTHY, and NECESSARY for him to feel those feelings, and think those thoughts.
