It’s not your job.
When someone you care about says they’re “fine” and you know they aren’t fine, you should press a little. But after a couple of attempts, can I suggest it’s now their responsibility to own their own feelings and fess up? It is not your job to chase after another adult and coax them into talking about their feelings.
Learn to be okay with people feeling how they feel.
Just like it is not anyone else’s job to make us feel better, we extend the same accountability to others.