Originally Posted by
courageouscrane 
He is borrowing money from his parents for rent, legal fees (DUI in February), has $100k of debt, and NOT looking for jobs.
Beyond the alcoholism, this should be a BIG red flag. This person sounds like they have a lot of work to do to become a functioning adult. Perhaps you should find someone who more closely shares your ambition to be successful and matches your maturity level.
I know it is hard when there are romantic feelings clouding the issue, but it sure seems like you aren't "settling for less" in the other areas of your life...