Though it may make you cringe, you should ask him how much he makes. Don’t guess based on his firm or industry. Assumptions won’t cut it. Find out exactly how much he’s taking home every paycheck to get a sense of what his money situation is like now. He may be up for a promotion, but what if he doesn’t get it? This cuts both ways, though. You’ll both need to see how much the other is bringing in to even begin a reasonable discussion about what you can and can’t afford as a couple.
Student loans, who doesn’t have them? But five maxed-out credit cards is another story — one he better have an explanation for. Of course you’ll want to know exactly how much he owes. But more important is the issue of whether he’s paying it down. No plan in place should be considered a billowing red flag. You don’t want your credit suffering because his has.