So my boyfriend of 5 or so months is unemployed. He's been like this pararently since we met. He has a record so its hard to get a job but he said he could possibly get a pardon to get rid of it but then recently he said he couldn't get it. Like I don't understand. He always tells me its his problem and for me to stay out his business but then he asks me for money. He's too old to be asking me for money and I'm too young to be giving someone his age money. He's emotionally support me unlike my family but he's not financially stable and that bothers me.

You have asked this question before and it seems no closer to resolution than you were 2 months ago. You have to be able to talk about this and set some boundaries. You can't be told to stay out of his business when he is borrowing money from you, or you are paying for everything when you are out on dates.

Its more difficult when you are starting to be emotionally dependent on him too. That's a double whammy that throws any good orderly direction way out of balance. You may never change him, or be able to resolve this to both your benefits without his being willing to do his part, and to be frank he seems very unwilling at this time to even talk to you let alone talk and LISTEN.

Clearly you need to back off, and reduce your emotional dependence on him greatly by limiting contact, or even think about ending this thing. I know that's so hard, and unthinkable for you, but it will be a lot harder the deeper you get into him. Maybe you approach him with blunt straight up honesty then, and let him know that while you are together/dating, unless he can talk about HIS business, you have NO business together.

My second suggestion is stop giving him money, and see where that gets you. If you have to give a guy money to keep his emotional support, then he isn't worth it. Relax though because I know for a fact, if something doesn't change for the better, you will dump him, because you will be sick and tired of (t)his crap, or he dumps you because you won't financially support him any longer.

You can only go so long without things getting better before you just get tired of it, and make a decision to change things. I think you are almost there to be honest.

And let me add this to what Tal already did an excellent job of answering....

Him having a record should only make it difficult to get certain kinds of work so he is pretty much just using this as an excuse to not have to work. I mean, why should he work when you're supporting him? Don't believe the crap. There are jobs out there if he is willing to do them.