The biggest problem lies in that he brought up moving in together next year, and seemed to have taken a lot of steps towards preparing himself for that, and then last week over drafted his checking account, again, and now another two weeks will go by without us being able to do anything that costs money.

How can I seriously share an apartment with someone like that? It's really sad to me to lose out on a sweet guy that I love simply because he's financially stupid.

- Not His Mom in Bangor

Dear Not His Mom,

Short answer? You can't. And shouldn't.

What we have here is a very special sort of loser - the stealth loser. The stealth loser is the guy who, despite his many faults, gives off an air of potential that makes otherwise rational women who should know better think they can change him. Take it from me: he will not change. Ever.

This guy has got some serious shortcomings that no amount of sweetness can possibly make up for. Look, I'm glad you like him and I'm sure he's a charming guy; hell, he'd have to be to land an understanding mate such as yourself - particularly considering his circumstances. But you deserve better than this. You really do. If you hitch your wagon to this guy, you'll just be dragging an anchor until you finally wise up and cut the cord.

It's ridiculous for you to have to curtail your own life because Skippy can't keep 20 bucks in his pocket. Oh, and by the way? Nice job on not playing banker. Enabling this guy will do nothing but throw gasoline on the fire.

Responsibility is the biggest key to being a stand-up guy, but it sounds like this dude is more than content to just keep right on sitting.