He seems to have mixed up "living in their mother's basement" and "hiding behind their mother's skirt," or it's just really, really awkward word choice. Because :autism:.
I think he's been in debt for at least fifteen years. Really, though, he's a credit card company's ideal customer--he has a shit-ton of debt that he's never going to completely pay off, he has a ton of cards (hell, one of them has "Christia Westonchandler" as the name on it, IIRC) which he keeps maxing out, and he always pays the minimums. To him, it's free money, and the credit card companies see it the exact same way.
Totes Sweet and Sparkles!