Darling, he's not struggling. He's playing while you struggle. As long as he knows he can fall back on you, why should he do boring things like get a part-time job to help pay the rent.

Why he's the way he is with money is not important at this moment.

What you're going to do and how you're going to do it are the more important questions.

You know what you want and need to do and that's to stop paying his way. First off, you can Just Say No (thank you, Nancy Reagan) to paying his loans, credit cards and whatever other debts he runs up. Practice saying it. No. No. No! NO!

I bring up the Just Say No campaign because it was aimed at steering young people away from drugs. Well, is there any drug stronger than love? And feeling needed? This guy has been able to sweet talk you into giving him money against your better judgment, so practicing saying no may be an important skill for you.

You need a place to live and if you live in NYC that doesn't come cheap. Not paying the rent, even if he doesn't have his share, would be a bad choice because you don't want to end up homeless in the city. But if he doesn't start pulling his own weight, you may need to figure out how to end this whole thing with him, find a new place or find a roommate who will pay up.

You might consider some self-help groups like Co-dependents Anonymous. You might get some books like Co-dependent No More or Women Who Love Too Much. As soon as you started paying his student loans when your weren't rolling in wealth yourself you kinda sorta displayed some glaring co-de signs right there and when you continued to pay his way despite not getting paid back, you sealed the deal.

It's important to get some help, either self-help or professional help, because even if you break it off with your Dreamer boyfriend, you're in serious danger of getting involved with another workless, but dreamy, man and paying his way again. Why?

Because when push comes to shove, bottom line, the final analysis, all those good cliches -- it's about the person who keeps giving and giving when they get only empty promises in return. That's the person who needs help.

I'm all for giving. I'm a giver myself. But there's a point where generosity can become pathologically enabling and it's no longer healthy or even generous. It wouldn't hurt to take a look at that more deeply. I wish you the best. It's not easy to break free from this dynamic of dysfunction. But it can be done and your life will be immensely better for it. Take Care.