He will not learn how to handle money if you continue to bail him out of his jams. Unless the bills are something that you and he both agreed upon and were necessary for living, etc., I would step back and allow him to figure out how to pay them. He's a big boy and I'm sure he'll find a way to do it w/o "mom's" help.
I know you are a fixer and this is tough, but you've got to allow your man/child to grow up on his own.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.