I think your partner lives by the old maxim: "What's thine is mine; what's mine is my own."

So the boy lived in the home occupied by his bio mom until he was 11 y.o. (She moved from "the home he grew up in.") So he grew up in that home, but he wasn't really raised there. Your narrative gets a bit tortuous. In any case, he's a real good kid, with whom you have a close and warm relationship.

Your partner owes you $96,000. Maybe, if his law practice continues to do great, you'll get some more large checks from his business. As you say, those disbursements should reduce the tax liability of his practice, which increases the total of your combined incomes. He, however, doesn't seem to think in terms of your joint financial situation . . . except when it suits him to do that because he wants to press a claim on your assets. With an income of $3000/mon, you're not exactly rolling in dough. You have considerable assets, which you may need in later years. He seems to not think very much about the retirement years. That makes me suspect that those years are further ahead for him than they are for you. By any chance is he 5 or 10 years younger than you?

Of the money he owes you, $30,000 is covered by a promissory note. That can be enforced legally, as I'm sure you know. Taking a romantic partner to court, however, tends to torpedo the romance. I think he doubts that you'll want to do that. Still, he might pay up. Then, again, when the novelty of the new car wears off, he'll likely yearn for some other new, shiney ego booster - maybe a boat. I doubt you'll ever get that older $66,000 back. I think that was the price you paid for setting up a scenario where you got to feel like a spouse and mother. He wants the best for his kids, as long as he can get someone else to provide it - right down to their birthday gifts and Christmas presents. That 13 year old has a nice bedroom because you provided it. Does Dad have anything put aside for this boy's education? You buy the boy's expensive sneakers and keep him smartly dressed. But Dad puts his kids first? Hmmm. He sure gets a lot for his thousand bucks a month. I know a divorced mother of a teen whose blue collar father has to send her $700/mon in child support. This guy of yours sure knows how to cut a deal for himself. Then he's got the kid who dropped out of school. That young person will probably need a helping hand soon enough. How will Dad help out that child, when he can't manage to pay credit cards on time. If he does respond to the needs of an older child, that will be his excuse for why he can't pay you. He'll self-righteously say, "How can you pressure me when I'm trying to think of our children?" You'll be the bad one the way he'll tell it.

Clover, you're educated and financially sophisticated. For over a decade, you've declined marrying this guy. I think that was wise of you. I believe you are enough of a survivor to know better than to ever put his name on the deed to your house. You structured this relationship so that you could keep one foot in, but have one foot out. (Been there and done that, myself.) With an irresponsible partner, there may not be a better alternative. But everything in life exacts a price. I hope you will always keep secure your title to your home. No more ELoCs. No more loans, period. The man is not creditworthy. Let him do his future borrowing from banks. They can afford a loss better than you can. If they won't lend to him, neither should you.

He's an attorney, past the age of 45, who needs to borrow his girlfriend's credit card? The man has character deficits that he will not live long enough to evolve beyond, even with the help of a team of steller therapists meeting with him daily. It's sad that he had a drunken father. It's sad that he's so damaged. He may truly be doing the best he can make himself do. But what you see is what you get. Avoid buying into the delusion that he can "work through" his "issues," if you just give him more time and another $60,000 in exchange for some heartfelt sounding promise. When he signed that promissory note, he intended to pay you back. He only breaks promises when he discovers they're hard to keep. He'll go to his grave doing that. Character is durable. Lack of character is durable.

I'm not saying dump him. Keep him, if you want him. Just recognize who he is. Don't ask him to be who he is not. It's not wrong to love a deeply flawed person. Just don't lend him money.